DOCSLIB.ORG

United States Patent Office Patented Jan

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent Office Patented Jan 3,230,260 United States Patent Office Patented Jan. 18, 1966 2 3,230,260 acid this does not occur. Thus the relatively non-volatile PROCESS FOR THE SOLATION OF N,O-DIMETH acid salts of N,O-dimethylhydroxylamine can be formed YLHYDROXYLAMINE Such as the hydrochloride, the sulfate or hydrogen sul Jack A. Snyder, Claymont, Del, assignor to E. I. du Pont fate. Sulfamic acid or phosphoric acid can similarly be de Nemours and Company, Wilmington, Del, a cor 5 used though they are less preferred. An amount of acid poration of Delaware can be used which is at least stoichiometrically equivalent No Drawing. Filed May 26, 1961, Ser. No. 112,772 to N.O-dimethylhydroxylamine and is preferred. Less 2 Claims. (C. 260-583) than stoichiometric amounts can be used though as less This invention relates to the preparation of N.O-di and less acid is used there will be loss of yield. While methylhydroxylamine. The invention is more particu O the processes of the invention can be operated with a pH larly directed to processes for the isolation of NO up to about 9, it is ordinarily preferred to use a pH dimethylhydroxylamine from a mixture of O-methylhy around 1 or 2. droxylamine and N,O-dimethylhydroxylamine by adding The amount of O-methylhydroxylamine and N.O-di formaldehyde thereby to convert O-methylhydroxylamine methylhydroxylamine dissolved in an aqueous solution to O-methylformaldoxime which escapes as a gas. 5 will ordinarily be of the order of 1 molar though it can By the methylation of hydroxyurethane followed by be higher or lower. The molarity of O-methylhydroxyl hydrolysis and distillation, one can make a mixture of amine and N.O-dimethylhydroxylamine combined can O-methylhydroxylamine and N.O - dimethylhydroxyla often run to 2 molar though there is no reason why it mine. The methylation produces additional materials as should not go up to 5 or 6 or even more. does the hydrolysis but these are separated out, for the 20 According to the invention formaldehyde is used to most part, in the distillation. Such a process is described effect a conversion of O-methylhydroxylamine to in Major and Fleck J.A.C.S. 50 1479 (1928). O-methylformaldoxime. The formaldehyde can be the A material produced as just described or a mixture of ordinary formalin solutions of commerce which contain O-methylhydroxylamine and N.O-dimethylhydroxylamine about 37% CHO and small amount of methanol. Other prepared in any fashion can be employed as a starting 25 forms of formaldehyde can equally well be used depend material in processes of the present invention. O-methyl ing upon the process equipment and one can for example hydroxylamine and N.O-dimethylhydroxylamine are ex use gaseous CH2O. Similarly, aqueous solutions of tremely difficult to separate by ordinary means because formaldehyde can be used which are produced by depo N,O - dimethylhydroxylamine boils at 42 C. and lymerization of paraformaldehyde by using a little caustic. O-methylhydroxylamine boils at 48 C. The difference 30 The techniques of supplying substantially monomeric of only 6 degrees makes separation by distillation vir formaldehyde for reaction are well understood. tually impossible and it is made even more difficult by The amount of formaldehyde to use is, of course, de the desired product being the lower boiling of the two. termined by the amount of O-methylhydroxylamine in a According to the present invention O-methylhydroxyl mixture to be treated. The formaldehyde reacts stoi amine and N.O-dimethylhydroxylamine are separated by 35 chiometrically with O-methylhydroxylamine and should the addition of formaldehyde, preferably in acid solution, be used in an amount to remove whatever proportion of to leave N.O-dimethylhydroxylamine substantially un O-methylhydroxylamine one wishes to take out of the changed and to produce O-methylformaldoxime which, mixture. Ordinarily it is desired to take out all in which being volatile, escapes as a gas. This reaction and case a slight excess of formaldehyde would ordinarily be procedure can be illustrated as follows: 40 employed. Even a large excess can be used because the I CH3ONE acid III CEON=CH formaldehyde is readily removed from the product Wutil CH2O --> the O-methylformaldoxime by distillation. II CHONECH3 I CEONHCH3 The reaction of formaldehyde can be conducted at In the above: room temperatures but can also be operated at higher 45 temperatures in which event the subsequent heating step I is O-methylhydroxylamine, which is preferred becomes a part of the formaldehyde II is N,O-dimethylhydroxylamine, and addition step and not a separate operation. III is O-methylformaldoxime. After O-methylformaldoxime has been formed or is In addition to O-methylhydroxylamine and N.O-di forming it is ordinarily desired to heat the aqueous solu methylhydroxylamine a commercial mixture often con 50 tion to reflux temperatures, that is to say temperatures tains other materials depending upon the process of pro near 100° C. O-methylformaldoxime which because of duction. Ordinarily such additional materials can be its volatility is already leaving the solution is driven off separated by conventional means either before or after more completely by the elevated temperature. Formal treatment according to the present invention. dehyde, too, is driven from the solution by the heating. The relative proportions of O-methylhydroxylamine 55 After O-methylformaldoxime and formaldehyde have and N,O-dimethylhydroxylamine can vary over a wide been driven from the solution it is cooled and the pH is range depending upon the completeness of the methyla raised by the addition of a suitable alkali such as sodium tion in the process by which they are produced or, more hydroxide. The pH should be above 4 and it is preferred broadly, depending upon the process by which they are that it be above 6. Ordinarily the pH will be above 7. produced. For purposes of the present invention it is 60 The exact pH is not at all critical. immaterial how much of O-methylhydroxylamine is The product, N.O-dimethylhydroxylamine, is then re present with N.O-dimethylhydroxylamine because any moved by distillation and it is to be observed that as the where from near traces up to quite substantial amounts product is removed the pH tends to fall and it should can be removed. be kept above 4 or preferably above 6 or 7 as above noted Processes of the invention are ordinarily conducted in 65 by further additions of alkali. Alternatively one can aqueous solutions and it is more desired that the solution use larger amounts of alkali initially. be at a pH below 7. The reason for having a low pH In order that the invention may be better understood is that if NO-dimethylhydroxylamine is present in the reference should be had to the following illustrative ex free state as an amine the escaping O-methylformald amples: oxime will tend to carry some of the N.O-dimethylhy 70 Example 1 droxylamine with it, thus leading to a loss in yield. If NO-dimethylhydroxylamine is combined with an A mixture of O-methylhydroxylamine hydrochloride 3,230,260 3 4. and N.O-dimethylhydroxylamine hydrochloride is pre heated to the reflux temperature and gaseous O-methyl pared as described by Major and Fleck except that the formaldoxime and excess formaldehyde are distilled over crude amine hydrochloride mixture is not recrystallized with about 200 ml, of water. The acidic solution is made after evaporation to remove alcohol and other volatiles. alkaline with 80 parts by weight of 50% aqueous NaOH, An aqueous solution of the mixed amine hydrochlorides and the freed amines are distilled. Two 100 ml. aqueous is prepared which has the following composition: amine fractions are taken. The first fraction proved to Percent contain all the amines. Analysis by gas chromatography O-methylhydroxylamine --------------------- 2.2 indicates the following recoveries of amines: N.O-dimethylhydroxylamine ------------------ 15.25 Parts by weight Hydroxylamine and other unidentified 10 O-methylhydroxylamine --------- Absent. basic impurities -------------------------- 1.3 N.O-dimethylhydroxylamine ------ 26.3 (0.43 mole). To 600 parts by weight of the above solution contain N,NO-trimethylhydroxylamine --- 1.2 (0.016 mole). ing 91.6 parts by weight (1.50 moles) of N.O-dimethyl Thus, the O-methylhydroxylamine has been completely hydroxylamine and 13.2 parts by weight (0.28 moles) of 15 eliminated from the solution while the desired N.O-di O-methylhydroxylamine at approximately pH 2.0 is added methylhydroxylamine is recovered substantially undimin 25.8 parts by weight (a 10% excess) of 36% aqueous ished. Instead of using sulfuric acid as in the above ex formaldehyde (9.3 parts by weight, 0.31 moles HCHO). ample there can be used molecularly equivalent amounts The resulting solution is heated slowly to reflux while of hydrochloric acid (Example 1), or phosphoric acid or gases from the top of the condenser operating at 10 C. 20 any other non-reactive acid of sufficient strength to fix the are led into a trap cooled by solid carbon dioxide and ace amine in substantially non-volatile condition during re tone. Gaseous O-methylformaldoxime is evolved from moval of excess formaldehyde. about 30° C. up to the reflux temperature. About 17 I claim: parts by weight of solid is collected in the trap (theoret 1. A process for isolating N.O-dimethylhydroxylamine ical: CHON=CH 16.5 parts by weight). The solid 25 from a mixture of O-methylhydroxylamine and N.O-di melted at about -65 C. and boiled at about -12 C. methylhydroxylamine by adding formaldehyde to an The corresponding constants for O-methylformaldoxime aqueous solution of O-methylhydroxylamine and N.O- are B.P.
Load more

Recommended publications
  • Mechanistic Aspects of the Reaction of Oxime Tosylates with Grignard Reagents
    University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Spring 1965 MECHANISTIC ASPECTS OF THE REACTION OF OXIME TOSYLATES WITH GRIGNARD REAGENTS STANFORD SALAVATORE PELOSI JR. Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation PELOSI, STANFORD SALAVATORE JR., "MECHANISTIC ASPECTS OF THE REACTION OF OXIME TOSYLATES WITH GRIGNARD REAGENTS" (1965). Doctoral Dissertations. 811. https://scholars.unh.edu/dissertation/811 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. This dissertation has been 65-9084 microfilmed exactly as received PELOSI, Jr., Stanford Salvatore, 1938- MECHANISTIC ASPECTS OF THE REACTION OF OXIME TOSYLATES WITH GRIGNARD REAGENTS. i University of New Hampshire, Ph.D., 1965 ; Chemistry, organic i I i University Microfilms, Inc., Ann Arbor, Michigan i Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. MECHANISTIC ASPECTS OF THE REACTION OF OXIME TOSYLATES WITH GRIGNARD REAGENTS BY STANFORD SALVATORE PELOSI, JR. B. S., Boston College, 1960 A THESIS Submitted to the University of New Hampshire, In Partial Fulfillment of The Requirements for the Degree of Doctor of Philosophy Graduate School Department of Chemistry March, 1965 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. This thesis has been examined .and approved. I | :.c < I ' l Y . 7 1 / 1 / Ctrvi HS Dat Reproduced with permission of the copyright owner.
    [Show full text]
  • Enhanced Isotopic Ratio Outlier Analysis (IROA) Peak Detection and Identification with Ultra-High Resolution GC-Orbitrap/MS
    H OH metabolites OH Article Enhanced Isotopic Ratio Outlier Analysis (IROA) Peak Detection and Identification with Ultra-High Resolution GC-Orbitrap/MS: Potential Application for Investigation of Model Organism Metabolomes Yunping Qiu 1 ID , Robyn D. Moir 2, Ian M. Willis 2, Suresh Seethapathy 3, Robert C. Biniakewitz 3 and Irwin J. Kurland 1,* 1 Stable Isotope and Metabolomics Core Facility, Diabetes Center, Department of Medicine, Albert Einstein College of Medicine, Bronx, NY 10461, USA; [email protected] 2 Department of Biochemistry, Albert Einstein College of Medicine, Bronx, NY 10461, USA; [email protected] (R.D.M.); [email protected] (I.M.W.) 3 Thermo Fisher Scientific, Somerset, NJ 08873, USA; suresh.seethapathy@thermofisher.com (S.S.); [email protected] (R.C.B.) * Correspondence: [email protected]; Tel.: +1-718-678-1091 Received: 7 November 2017; Accepted: 10 January 2018; Published: 18 January 2018 Abstract: Identifying non-annotated peaks may have a significant impact on the understanding of biological systems. In silico methodologies have focused on ESI LC/MS/MS for identifying non-annotated MS peaks. In this study, we employed in silico methodology to develop an Isotopic Ratio Outlier Analysis (IROA) workflow using enhanced mass spectrometric data acquired with the ultra-high resolution GC-Orbitrap/MS to determine the identity of non-annotated metabolites. The higher resolution of the GC-Orbitrap/MS, together with its wide dynamic range, resulted in more IROA peak pairs detected, and increased reliability of chemical formulae generation (CFG). IROA uses two different 13C-enriched carbon sources (randomized 95% 12C and 95% 13C) to produce mirror image isotopologue pairs, whose mass difference reveals the carbon chain length (n), which aids in the identification of endogenous metabolites.
    [Show full text]
  • Important Features of the Potential Energy Surface of the Methylamine Plus O(1D) Reaction
    Physical Chemistry Chemical Physics Important Features of the Potential Energy Surface of the Methylamine Plus O(1D) Reaction Journal: Physical Chemistry Chemical Physics Manuscript ID CP-ART-09-2019-005039.R1 Article Type: Paper Date Submitted by the 17-Oct-2019 Author: Complete List of Authors: Wolf, Mark; University of Georgia , Center for Computational Quantum Chemsitry; Hoobler, Preston; Covenant College, Chemistry; University of Georgia Franklin College of Arts and Sciences, Center for Computational Quantum Chemistry Turney, Justin; University of Georgia, Center for Computational Chemistry Schaefer, Henry; University of Georgia, Computational Chemistry Page 1 of 13 Physical Chemistry Chemical Physics Journal Name Important Features of the Potential Energy Surface of the Methy- lamine Plus O(1D) Reaction † Mark E. Wolf, Preston R. Hoobler, Justin M. Turney, and Henry F. Schaefer III∗ This research presents an ab initio characterization of the potential energy surface for the methy- lamine plus 1D oxygen atom reaction, which may be relevant to interstellar chemistry. Ge- ometries and harmonic vibrational frequencies were determined for all stationary points at the CCSD(T)/aug-cc-pVTZ level of theory. The focal point method along with several additive correc- tions was used to obtain reliable CCSDT(Q)/CBS potential energy surface features. Extensive conformational analysis and intrinsic reaction coordinate computations were performed to ensure accurate chemical connectivity of the stationary points. Five minima were determined to be pos- sible products of this reaction and three novel transition states were found that were previously unreported or mislabeled in the literature. The pathways we present can be used to guide further searches for NH2 containing species in the interstellar medium.
    [Show full text]
  • Inhibition of DNA Synthesis by Hydroxyurea: Structure-Activity Relationships1
    [CANCER RESEARCH 27 Part 1, 535-540, March 1967] Inhibition of DNA Synthesis by Hydroxyurea: Structure-Activity Relationships1 CHARLES W. YOUNG, GERALD SCHOCHETMAN, SADIE HODAS, AND M. EARL BALIS Divisions of Clinical Chemothirapy and Biological Chemistry, Sloan-Ketlering Institute for Cancer Research, New York, New York 10021 SUMMARY allosteric effectors, altering substrate specificity and the rate of The following comix>unds inhibited incorporation of thy- the overall reaction (12, 13). The molecular mechanism by which midine-3H into the DNA of HeLa cells without significantly hydroxyurea inhibits deoxyribonucleotide synthesis is not known. impairing cellular incorjwration of uridine-3H into RNA or Substrate attack is unlikely because the drug does not impair loucine-3H into protein; the}' are listed in order of potency. synthesis of RNA; an attack ui>on the product of the reaction Dihydro.xyurea > jV-methylhydroxyurea > .V-acetylhydroxy- (deoxyribonucleotides) could not be demonstrated in ex|>eriments urea = hydroxyurea = A'-hydroxyguanidine = N-hydroxyure- with cell-free extracts (26). Because of the lack of structural thane = AT-ethylhydroxyurea > 3-phenyl-l-hydroxyurea = analogy between hydroxyurea and ribonucleotides or deoxyribo formamidoxime > Ar-mcthylacetohydroxamic acid = Ar-methyl- nucleotides, competition by the drug for the enzymatic substrate and/or allosteric-effector sites seems improbable. In an effort to hydroxylamine > acetohydroxamio acid. Hydroxylamine, JV-hydroxyglycine amide and 3-phenyl-l-hydroxy-2-thiourea clarify the relationship between molecular structure and inhibi tory activity, we have studied the effects of various hydroxyl- inhibited incori>oration of all three labeled precursors. Methoxy- amine, methoxyurea, and Ar-methylmethoxyurea had no effect amine and hydroxamic acid derivatives u)xjn protein and nucleic acid metabolism in HeLa cells.
    [Show full text]
  • Assessing the Chemistry and Bioavailability of Dissolved Organic Matter from Glaciers and Rock 2 Glaciers 3
    bioRxiv preprint doi: https://doi.org/10.1101/115808; this version posted April 11, 2019. The copyright holder for this preprint (which was not certified by peer review) is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. It is made available under aCC-BY-NC-ND 4.0 International license. 1 ASSESSING THE CHEMISTRY AND BIOAVAILABILITY OF DISSOLVED ORGANIC MATTER FROM GLACIERS AND ROCK 2 GLACIERS 3 4 1,2 1,3 3 1,4 5 Fegel, Timothy , Boot, Claudia M. , Broeckling, Corey D. , Hall, Ed K. 6 1. Natural Resource Ecology Laboratory, Colorado State University 2. U.S. Forest Service, 7 Rocky Mountain Research Station, 3. Department of Chemistry, Colorado State University 4. 8 Proteomics and Metabolomics Facility, Colorado State University 4. Department of Ecosystem 9 Science and Sustainability, Colorado State University 10 11 Tim Fegel [email protected] 12 13 14 Key Points: 15 Bioavailability of organic matter released from glaciers is greater than that of rock glaciers in the 16 Rocky Mountains. 17 The use of GC-MS for ecosystem metabolomics represents a novel approach for examining 18 complex organic matter pools. 19 Both glaciers and rock glaciers supply highly bioavailable sources of organic matter to alpine 20 headwaters in Colorado. 1 bioRxiv preprint doi: https://doi.org/10.1101/115808; this version posted April 11, 2019. The copyright holder for this preprint (which was not certified by peer review) is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. It is made available under aCC-BY-NC-ND 4.0 International license.
    [Show full text]
  • The Development of Novel Biocatalysts for the Asymmetric Hydroamination of Alkenes
    The Development of Novel Biocatalysts for the Asymmetric Hydroamination of Alkenes A Thesis Submitted to the University of Manchester for the Degree of Doctor of Philosophy in the Faculty of Engineering and Physical Sciences 2014 Sarah Louise Lovelock School of Chemistry 1 Contents List of Figures .............................................................................................................................. 5 List of Schemes ........................................................................................................................... 8 List of Tables ............................................................................................................................. 10 Abstract ..................................................................................................................................... 12 Declaration ................................................................................................................................ 13 Copyright Statement ................................................................................................................. 14 Acknowledgements ................................................................................................................... 15 Abbreviations ............................................................................................................................ 16 Chapter 1: Introduction .......................................................................................................... 18 1.1 Introduction
    [Show full text]
  • Mechanic Aspects and Parameters for Biological Effect Monitoring
    Erythrotoxicity of aliphatic hydroxylamines : mechanic aspects and parameters for biological effect monitoring Citation for published version (APA): Spooren, A. A. M. G. (2000). Erythrotoxicity of aliphatic hydroxylamines : mechanic aspects and parameters for biological effect monitoring. UM. https://doi.org/10.26481/dis.20001026as Document status and date: Published: 01/01/2000 DOI: 10.26481/dis.20001026as Document Version: Publisher's PDF, also known as Version of record Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website. • The final author version and the galley proof are versions of the publication after peer review. • The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal.
    [Show full text]
  • Methanamine, N-Methoxy
    Methanamine, N-methoxy- Other names: CH3NHOCH3; Hydroxylamine, N,O-dimethyl-; Methoxyamine, N-methyl-; Methoxymethylamine; Methylamine, N-methoxy-; N,O-Dimethylhydroxylamine; N-Methoxy-N-methylamine; N-Methoxymethylamine; N-Methyl-O-methylhydroxylamine; N-Methylmethoxyamine; O,N-Dimethylhydroxylamine; O-Methyl-N-methylhydroxylamine. InChI: InChI=1S/C2H7NO/c1-3-4-2/h3H,1-2H3 InChI Key: KRKPYFLIYNGWTE-UHFFFAOYSA-N Formula: C2H7NO SMILES: CNOC Molecular Weight: 61.08 CAS: 1117-97-1 Physical Properties Property Value Unit Source ∆ G° -49.65 kJ/mol Joback Method f ∆ H° -163.36 Joback Method f gas kJ/mol ∆ H° 7.22 Joback Method fus kJ/mol ∆ H° 28.89 Joback Method vap kJ/mol IE 8.92 eV NIST Webbook logP -0.23 Crippen Method oct/wat P 5001.51 Joback Method c kPa T 317.75 Joback Method boil K T 488.59 Joback Method c K T 187.19 Joback Method fus K V 0.20 3 Joback Method c m /kg-mol Temperature Dependent Properties Property Value Unit Temperature (K) Source C 87.78 J/mol×K 317.75 Joback Method p,gas Property Value Unit Temperature (K) Source ∆ H 34.30 272.0 NIST Webbook vap kJ/mol Sources Joback Method: https://en.wikipedia.org/wiki/Joback_method NIST Webbook: http://webbook.nist.gov/cgi/inchi/InChI=1S/C2H7NO/c1-3-4-2/h3H,1-2H3 Crippen Method: http://pubs.acs.org/doi/abs/10.1021/ci990307l Legend C : Ideal gas heat capacity (J/mol×K). p,gas ∆ G°: Standard Gibbs free energy of formation (kJ/mol). f ∆ H° : Enthalpy of formation at standard conditions (kJ/mol).
    [Show full text]
  • The Section of the Template to Be Replaced (E
    Issue in Honor of Prof. William F. Bailey ARKIVOC 2011 (v) 230-262 Synthesis of amines by the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents Tahir Daşkapan Department of Chemistry, Ankara University Science Faculty, 06100 Beşevler, Ankara, Turkey E-mail: [email protected] Dedicated to Professor William F. Bailey on occasion of his 65th birthday DOI: http://dx.doi.org/10.3998/ark.5550190.0012.520 Contents 1. Introduction 2. Electrophilic Amination of Organomagnesium Reagents 3. Electrophilic Amination of Organozinc Reagents 4. Electrophilic Amination of Organocopper Reagents 5. Electrophilic Amination of Organolithium Reagents 6. Conclusions 7. Acknowledgement 8. References 1. Introduction Amines are important building blocks in the synthesis of various important organic compounds such as pharmaceuticals, agrochemicals, polymers, dyes, xerographic and photographic materials.1-5 Therefore, development of new synthetic methods for amines has attracted the attention of many researchers.6-11 Among modern amination methods, electrophilic amination of an easily available organometallic reagent has been found to be a viable alternative method and continues to be an active area for research in synthetic organic chemistry.12-16 To date various type of aminating reagents have been used in the electrophilic amination of organomagnesium, -zinc, -copper, and -lithium reagents for the introduction of free or protected amino moieties, such as haloamines, substituted hydroxylamines, imines, oxaziridines, oximes, diazonium salts, azodicarboxylates, azides, and metal amides. This review covers the literature published in the last twenty years in detail. In addition, older literature has been mentioned briefly. Page 230 ©ARKAT USA, Inc. Issue in Honor of Prof. William F.
    [Show full text]
  • Chemical Classification List
    Identifier/CAS # Name Group # 5683-31-8 3-(Trimethylsilyl)propynoic acid 1 21293-29-8 (+)-Abscisic acid, (2, 4-pentadienoic acid) 1 14375-45-2 (±)-Abscisic acid 1 35963-20-3 (1R)-(-)-10-Camphorsulfonic acid 1 3144-16-9 (1S)-(+)-10-Camphorsulfonic acid 1 2444-37-3 (Methylthio)acetic acid 1 611-71-2 (R)-(−)-Mandelic acid 1 20445-31-2 (R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid 1 17257-71-5 (S)-(−)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid 1 17199-29-0 (S )-(+)-Mandelic acid 1 26164-26-1 (S)-(+)-α-Methoxyphenylacetic acid 1 1077-28-7 ±)-α-Lipoic acid, DL-6,8-thioctic acid 1 1703-58-8 1,2,3,4-Butanetetracarboxylic acid 1 3971-31-1 1,3-​Cyclohexanedicarboxylic acid 1 542-05-2 1,3-Acetonedicarboxylic acid 1 112-38-9 10-Undecenoic acid 1 2777-65-3 10-Undecynoic acid 1 71310-21-9 11-​Mercaptoundecanoic acid 1 2834-05-1 11-Bromoundecanoic acid 1 69839-68-5 16-​Mercaptohexadecanoic acid 1 4942-47-6 1-Adamantaneacetic acid 1 828-51-3 1-Adamantanecarboxylic acid 1 636-82-8 1-Cyclohexene-1-carboxylic acid 1 86-87-3 1-Naphthaleneacetic acid 1 3443-45-6 1-Pyrenebutyric acid 1 2062-25-1 2-(Trifluoromethyl)cinnamic acid 1 719-60-8 2,3,4,5,6-Pentafluorocinnamic acid 1 653-21-4 2,3,4,5,6-Pentafluorophenylacetic acid 1 94-75-7 2,4-D (2,4-Dichlorophenoxyacetic acid) 1 94-82-6 2,4-DB 1 89-86-1 2,4-Dihydroxybenzoic acid, Resorcylic acid 1 207234-00-2 2,4-Dinitrobenzenesulfonic acid dihydrate 1 490-79-9 2,5-Dihydroxybenzoic acid 1 1141-38-4 2,6-​Naphthalenedicarboxylic acid 1 80-58-0 2-Bromobutyric acid 1 70610-87-6 2-Bromooctanoic acid 1 584-93-0
    [Show full text]