Oxidizing Agents

Oxidation, which makes its target substance lose electrons, is ● Sodium Hypochlorite one of the most basic reactions in organic chemistry and is Sodium hypochlorite pentahydrate (NaClO·5H2O) [S0939] is a exemplified by the combination with oxygen or a dehydrogenation stable crystalline solid and effective for the oxidation of hydroxy reaction. In particular, oxidizing agents have often been used for and sulfide groups. For instance, S0939 can oxidize secondary the transformation of alcohols to the corresponding aldehydes, alcohols into ketones in the presence of a catalytic amount of ketones or carboxylic acids. Heavy metal compounds, such as TEMPO [T1560].6) S0939 is also utilized in the oxidative cleavage chromium(VI) oxide and potassium permanganate, have been of 1,2-diols7) and oxidation of sulfides.8) Sulfoxides and sulfones exploited for many years. Later, less harmful oxidizing agents can be synthesized in high yields by adjusting the equivalents of without heavy metals were developed, such as Dess-Martin S0939. Furthermore, it has recently been reported that S0939 is periodinane, the Mukaiyama oxidizing agent and oxoammonium useful for the convenient synthesis of hypervalent iodine salts. Moreover, oxidation reactions employing inexpensive compounds.9) cooxidants have been reported in the presence of oxidation catalysts like tetrapropylammonium perruthenate (TPAP) and NaClO·5H2O [S0939] OH cat. TEMPO [T1560] O cat.Bu NHSO [T0835] TEMPO. In this way, oxidation reactions involving organic CH3 4 4 CH3 CH3 CH3 CH2Cl2 compounds have great diversity, and many books on oxidation CH3 CH3 1) have been published. OH OH O S0939 This brochure introduces a variety of oxidizing agents and or AcOH catalysts for oxidation. We hope that it will be useful for your OH OH O research in organic synthesis. In addition, we have prepared S0939 (1.1 eq.) O another brochure, “Reducing Agents”, which is the reverse S CH3CN / H2O Ph CH3 S reaction to oxidation. Ph CH3 S0939 (2.4 eq.) O O S toluene / H2O Ph CH3

● Chromate Salts I AcO I OAc S0939 Jones et al. reported that a mixture of chromium oxide(VI) and AcOH diluted sulfuric acid was useful for the oxidation of alcohols, and this reaction is called Jones oxidation.2) It can convert primary and secondary alcohols into carboxylic acids and ketones, respectively. Since this report, chromium oxidants have been ● Criegee Oxidation improved to develop the Sarett-Collins oxidation3) process using Criegee oxidation gives two ketones or aldehydes from 1,2-diols complex chromium(VI) oxide-2py, pyridinium chlorochromate by using lead(IV) tetraacetate (LTA) [L0021] as an oxidant.10) This (PCC) [P0930]4) and pyridinium dichromate (PDC) [P0931].5) reaction is different from the oxidative cleavage reaction using These reagents can oxidize primary alcohols to aldehydes periodate salt (= Malprade reaction)11) and proceeds when applied without overreaction. to trans-1,2-diols, which would be difficult to pass through the five- Caution: Chromium(VI) compounds and the chromium residue membered intermediate. This indicates another reaction after the reaction are highly toxic, so they should be handled or mechanism that does not pass through the cyclic transition state. discarded with consideration to the environment.

OH LTA [L0021] O Jones oxidation Pb(OAc)2 OH O O cis-1,2-diol CrO3, H2SO4 O H2O OH O R OH O H2O / acetone OAc R H R OH R OH OH LTA [L0021] O Pb(OAc)2

OH same above O OH O H OAc trans-1,2-diol R1 R2 R1 R2 cf) Malaprade reaction

PCC and PDC oxidation OH - O O IO4 O O I O OH O O OH PCC [P0930] O PCC: ClCrO3 N H R1 R2 or R1 R2 PDC [P0931]

PDC: 2 Cr2O7 N H

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● Oxidation using Hypervalent Iodine One problem with DMSO oxidation is the odor of the byproduct Compounds dimethyl sulfide. To solve this problem, Togo et al. developed the Dess-Martin periodinane (DMP)12) [D2045] [D4477] can oxidize odorless and recyclable imidazolium salts [M2274] and [M2321] primary and secondary alcohols into aldehydes and ketones, for use in Swern oxidation21a) and Corey-Kim oxidation,21b) respectively. DMP has some advantages compared with respectively. chromate(VI) compounds: the reaction using DMP proceeds under mild conditions; the generality of reactive substrates is wide; the O environmental impact is lower; and the treatment after the reaction S S N CH N CH is easy. 2-Iodoxybenzoic acid (IBX)13) [I0791] and 1-acetoxy-5- 3 3 TsO TsO bromo-1,2-benziodoxol-3(1H)-one (ABBX)14) [A2678], which was N N CH CH developed by Togo, are also utilized as oxidants of alcohols as well 3 [M2274] 3 [M2321] as other hypervalent iodine compounds.15) These compounds are M2274 introduced in our brochure “Hypervalent Iodine Compounds”. (COCl)2 OH Et3N O

OAc O AcO I O R1 R2 CH2Cl2 R1 R2 AcO AcO I O HO I O O R1 = alkyl, aryl O O R2 = H, alkyl, aryl

Br M2321 NCS [C0291] DMP[D2045] IBX[I0791] ABBX[A2678] OH Et N O [D4477] 3 1 2 CH Cl 1 2 12b) R R 2 2 R R D2045 CHO 1 OH NaHCO3 R = alkyl, aryl R2 = H, alkyl, aryl CH3 CH2Cl2 CH3 CH3O CH3O

14) CHO OH A2678 R R DMF, ● Mukaiyama Oxidation Reaction Mukaiyama’s group reported two new oxidation reactions using N-tert-butylbenzenesulfinimidoyl chloride [B2188],22) and catalytic ● DMSO Oxidations and Odorless Swern amounts of N-tert-butylbenzenesulfenamide [B2240] and NCS Oxidants [C0291],23) respectively. It is considered that B2188 is generated Kornblum et al. found that the carbonyl group was produced from in situ by the reaction of B2240 and NCS, and turns into B2240 benzyl halides and tosylates by the treatment of DMSO [D0798] in after the reaction; thus B2240 works as a catalyst. B2188 is a the presence of a base.16) After this report, various types of stable solid and can give a,b-unsaturated ketones from an enolate oxidations using DMSO have been reported as follows: Pfitzner- by deprotonation at the a-position or 1,4-addition.24) In addition, Moffatt oxidation17) using DCC [D0436] or DCC (granulated) the new method has been reported to afford a ketone from an [D4876]; Albright-Goldman oxidation18) using acetic anhydride aldehyde, an alkyllithium and B2188 in one pot.25) 19) [A2036]; Parikh-Doering oxidation using SO3-pyridine complex [P0998]; and Swern oxidation20) using oxalyl chloride [O0082]. CH These reactions are utilized widely from the laboratory scale to the 3 Cl CH 3 S NH C CH3 industrial scale. SCN CH 3 CH3 CH3 Kornbrum oxidation X DMSO O [B2188] [B2240]

1 2 base 1 2 R R R R Oxidation of alcohols X = halogen, TsO NCS [C0291] B2240 B2188 23) Various DMSO oxidations

OH DMSO O OH O

1 2 1 2 R R R R R1 R2 base R1 R2 1 CH2Cl2 R = alkyl, aryl 1 R2 = H, alkyl, aryl R = alkyl, aryl R2 = H, alkyl, aryl

named reactions reagents

DCC [D0436] [D4876] Pfitzner-Moffatt oxid. TFA [T0431]

Albright-Goldman oxid. Ac2O [A2036]

Parikh-Doering oxid. SO3·py [P0998], Et3N [T0424] (COCl) [O0082] or TFAA [T0433] Swern oxid. 2 Et3N [T0424]

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● Catalytic Oxidation Reactions One-pot -substitution of enones 24) 1. Oxidation with TPAP Catalyst O RLi O CuCN [C1952] Tetrapropylammonium perruthenate (TPAP) [T1559] Et2O catalyst can oxidize alcohols into aldehydes and ketones

H then B2188 R by the addition of 4-methylmorpholine N-oxide (= NMO) 29) Ph Ph [M2192] as a cooxidant (Ley-Griffith oxidation). This

"RCu" reaction proceeds under very mild conditions to give the corresponding product in high yield even when applied to O O Ph unstable substances. Moreover, this reaction can oxidize S tBu B2188 N primary alcohols to carboxylic acids in the presence of water by hydration of the aldehyde to form a gem-diol and R H R 30) Ph Ph subsequent reoxidation. TPAP and NMO are often applied in the syntheses of natural products. Gaich’s group, for instance, have reported the total synthesis of ● Epoxidation Reaction (-)-leuconoxine by ingeniously applying this reaction at Epoxidation is also an oxidation reaction and the Prilezhaev the last step.31) (Prileschajew) reaction26) with mCPBA is regarded as a representative epoxidation. Furthermore, asymmetric epoxidation Ley-Griffith oxidation reactions have been reported such as Sharpless-Katsuki cat. TPAP [T1559] asymmetric epoxidation27) for allyl alcohols and Jacobsen- OH NMO [M2192] O Katsuki asymmetric epoxidation28) of cis-olefins. Sharpless- R1 R2 MS4A R1 R2 CH Cl (CH CN) R1 = alkyl, aryl 2 2 3 Katsuki asymmetric epoxidation is often used in the total R2 = H, alkyl, aryl syntheses of natural products. cat. TPAP [T1559] OH O NMO-H2O [M0981] R OH Prilezhaev epoxidation CH3CN R OH R OH

O O OH O O

cat. TPAP [T1559] Cl N Et N 1 2 1 2 NMO [M2192] R R mCPBA R O R H Et N H Et CH CN NH 3 N 4 3 4 3 R R R R HO HO O Sharpless-Katsuki asymmetric epoxidation

D-(-)-DET[T1195] Ti(OiPr)4[T0133] TBHP[B3153] O 2. Oxidation Using AZADOL® MS4A,CH2Cl2 R OH AZADOL® [H1404], known as the precursor of an R OH L-(+)-DET[T0003] oxidation catalyst, is a hydroxyamine developed by Ti(OiPr)4[T0133] 32) TBHP[B3153] O Iwabuchi et al. The oxidizing ability of H1404 is superior

MS4A,CH2Cl2 R OH to that of TEMPO [T1560], particularly for secondary alcohols. In addition, 1,2-diols are oxidatively cleaved by Jacobsen-Katsuki asymmetric epoxidation the treatment of a catalytic amount of PIDA [I0330] to 28c)

CH3 afford two carboxylic acids. H1404 is anticipated as a CH3 cat.B5613 O O aq.NaOCl CH3 CH3 green catalyst for oxidation since sodium hypochlorite, CH Cl 2 2 NC sodium chlorite and even oxygen in air can be utilized as NC aq.NaOH/NaHPO4 O cooxidants.

AZADOL® is a registered trademark of Nissan Chemical Corporation. N N CH3 CH3 Mn cat. AZADOL [H1404] CH3 C O Cl O C CH3 NaOCl OH O CH3 CH3 KBr, TBAB [T0054] CH3 C CH3 CH3 C CH3 R1 R2 CH2Cl2 / aq. NaHCO3 R1 R2 CH3 CH3 R1, R2 = alkyl, aryl (R,R)-Jacobsen'sCatalyst [B5613] O OH cat. AZADOL [H1404] R1 OH PIDA [I0330] R2 1 + R CH CN 3 O OH R2 OH

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16) a) N. Kornblum, J. W. Powers, G. J. Anderson, W. J. Jones, H. O. Larson, References O. Levand, W. M. Weaver, J. Am. Chem. Soc. 1957, 79, 6562. 1) a) T. J. Donohoe, Oxidation and Reduction in Organic Synthesis Oxford Univ b) N. Kornblum, W. J. Jones. G. J. Anderson, J. Am. Chem. Soc. 1959, 81, 4113. Pr on Demand, 2000. 17) a) K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 1963, 85, 3027. b) A. H. Haines, Methods for the Oxidation of Organic Compounds: Alcohols, b) K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 1965, 87, 5661. Alcohol Derivatives, Alky Halides, Nitroalkanes, Alkyl Azides, Carbonyl c) K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 1965, 87, 5670. Compounds, Hydroxyarenes and Aminoarenes, 1988. 18) J. D. Albright, L. Goldman, J. Am. Chem. Soc. 1967, 89, 2416. c) G. Tojo, M. I. Fernandez, Oxidation of Alcohols to Aldehydes and Ketones: 19) J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505. A Guide to Current Common Practice Springer, 2005. 20) a) A. K. Sharma, D. Swern, Terahedron Lett. 1974, 15, 1503. d) L. Kürti, B. Czakó, Strategic Applications of Named Reactions in Organic b) K. Omura, A. K. Sharma, D. Swern, J. Org. Chem. 1976, 41, 957. Synthesis, Elsevier, 2005. c) L. Huang, D. Swern, J. Org. Chem. 1978, 43, 4537. 2) K. Bowden, I. M. Heilbron, E. R. H. Jones, B. C. L. Weedon, J. Chem. Soc. 1946, d) K. Omura, D. Swern, Terahedron 1978, 34, 1651. 39. 21) a) D. Tsuchiya, K. Moriyama, H. Togo, Synlett 2011, 2701. 3) a) G. I. Poos, G. E. Arth, R. E. Beyler, L. H. Sarett, J. Am. Chem. Soc. 1953, 75, b) D. Tsuchiya, M. Tabata, K. Moriyama, H. Togo, Tetrahedron 2012, 68, 6849. 422. 22) T. Mukaiyama, J. Matsuo, D. Iida, H. Kitagawa, Chem. Lett. 2001, 30, 846. b) J. C. Collins, W. W. Hess, F. J. Frank, Terahedron Lett. 1968, 9, 3363. 23) T. Mukaiyama, J. Matsuo, M. Yanagisawa, Chem. Lett. 2000, 29, 1072. 4) E. J. Corey, J. W. Suggs, Terahedron Lett. 1975, 16, 2647. 24) a) J. Matsuo, Y. Aizawa, Chem. Comm. 2005, 2399. 5) E. J. Corey, G. Schmidt, Terahedron Lett. 1979, 20, 399. b) W. J. Kerr, C. M. Pearsona, G. J. Thurston, Org. Biomol. Chem. 2006, 4, 47. 6) T. Okada, T. Asawa, Y. Sugiyama, M. Kirihara, T. Iwai, Y. Kimura, Synlett 2014, 25) J. J. Crawford, K. W. Henderson, W. J. Kerr, Org. Lett. 2006, 8, 5073. 25, 596. 26) N. Prileschajew, Ber. 1909, 42, 4811. 7) M. Kirihara, R. Osugi, K. Saito, K. Adachi, K. Yamazaki, R. Matsushima, 27) a) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974. Y. Kimura, J. Org. Chem. 2019, 84, 8330. b) review: A. Pfenninger, Synthesis 1986, 89. 8) T. Okada, H. Matsumuro, S. Kitagawa, T. Iwai, K. Yamazaki, Y. Kinoshita, 28) a) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. Y. Kimura, M. Kirihara, Synlett 2015, 26, 2547. 1980, 102, 5974. 9) A. Watanabe, K. Miyamoto, T. Okada, T. Asawa, M. Uchiyama, J. Org. Chem. b) R. Irie, K. Noda, Y. Ito, T. Katsuki, Terahedron Lett. 1991, 32, 1055. 2018, 83, 14262. c) N. H. Lee, A. R. Muci, E. N. Jacobsen, Terahedron Lett. 1991, 32, 5055. 10) R. Criegee, Ber. 1933, 64, 260. 29) W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc., Chem. 11) a) L. Malaprade, Bull. Soc. Chim. Fr. 1934, 3, 833. Commun. 1987, 1625. b) P. Karrer, R. Hirohata, Helv. Chim. Acta 1933, 16, 959. 30) A.-K. C. Schmidt, C. B. W. Stark, Org. Lett. 2011, 13, 4164. 12) a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155. 31) M. Pfaffenbach, T. Gaich, Chem. Eur. J. 2015, 21, 6355. b) V. Beghetto, A. Scrivanti, M. Bertoldini, M. Aversa, A. Zancanaro, 32) a) M. Shibuya, Y. Sasano, M. Tomizawa, T. Hamada, M. Kozawa, N. Nagahama, U. Matteoli, Synthesis 2015, 47, 272. Y. Iwabuchi, Synthesis 2011, 21, 3418. 13) M. Frigerio, M. Santagostino, Terahedron Lett. 1994, 35, 8019. b) review: Y. Iwabuchi, Chem. Pharm. Bull. 2013, 61, 1197. 14) M. Iinuma, K. Moriyama, H. Togo, Eur. J. Org. Chem. 2014, 772. 33) M. Shibuya, T. Shibuta, H. Fukuda, Y. Iwabuchi, Org. Lett. 2012, 14, 5010. 15) review: a) H. Tohma, Y. Kita, Adv. Synth. Catal. 2004, 346, 111. b) A. Yoshimura, V. V. Zhdankin, Chem. Rev. 2016, 116, 3328.

P0930 25g 100g 500g P0931 25g 100g 500g B1123 10g

2 2- Cr2O7 2[(C4H9)4N] Cr2O7 Chromates N ClCrO3 N H H 2 Bis(tetrabutylammonium) PCC PDC Dichromate CAS RN: 26299-14-9 CAS RN: 20039-37-6 CAS RN: 56660-19-6 P1088 5g Q0058 10g 25g

2- FCrO Cr2O7 N 3 N H H 2 Pyridinium Fluorochromate Quinolinium Dichromate CAS RN: 83042-08-4 CAS RN: 56549-24-7 S0939 25g 500g

. Hypochlorites NaClO 5H2O Sodium Hypochlorite Pentahydrate CAS RN: 10022-70-5 T0836 25g 100g 500g

(CH2)3CH3 Perchlorates CH3(CH2)3 N (CH2)3CH3 ClO4 (CH2)3CH3 Tetrabutylammonium Perchlorate CAS RN: 1923-70-2 B3153 100g C2223 100g D3411 100mL

CH3 CH3 C OOH CH3 CH3 CH C OOH 3 CH Peroxides 3 CH3 C OOC CH3 CH3 Cumene Hydroperoxide CH CH (contains ca. 20% Aromatic 3 3 TBHP (70% in Water) Hydrocarbon) Di-tert-butyl Peroxide CAS RN: 75-91-2 CAS RN: 80-15-9 CAS RN: 110-05-4 D4894 100g 500g

CH3 CH3 C O O C

CH3 CH3 Dicumyl Peroxide (contains ca. 60% CaCO3) CAS RN: 80-43-3 D2045 1g 5g 25g D4477 25mL 250mL I0791 5g 25g O OAc HO I O AcO OAc AcO AcO I O AcO I O O Hypervalent Iodine O O IBX (stabilized with Benzoic DMP DMP (8-12% in Dichloromethane) Acid + Isophthalic Acid) CAS RN: 87413-09-0 CAS RN: 87413-09-0 CAS RN: 61717-82-6 A2678 1g I0330 10g 25g 250g I0479 5g 25g P1415 1g 5g B1616 1g 5g O O O O O O O CH CO IOCCH CH3 C O I O CH3 CO IOCCH3 3 3 O CF3 C O IOC CF3

CH3 CH3 O CCH3 F F O P I

OCCH3 F F Br CH3 O F ABBX PIDA Iodomesitylene Diacetate PSDIB FPIFA CAS RN: 1580548-81-7 CAS RN: 3240-34-4 CAS RN: 33035-41-5 CAS RN: 36290-94-5 CAS RN: 14353-88-9

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B5405 5g I0073 1g 10g B2539 1g P0077 25g

H3C O O CH3

H3C C C O I O C C CH3 HO I O

H3C CH3 O NIN BF4

[Bis(tert-butylcarbonyloxy)- iodo]benzene IBA Barluenga's Reagent Trisodium Paraperiodate CAS RN: 57357-20-7 CAS RN: 304-91-6 CAS RN: 15656-28-7 CAS RN: 13940-38-0 O0310 25g 500g P0998 25g 100g 500g T2136 5g 25g

CH 3 . . SO3 .. SO3 Sulfur Oxides 2KHSO5 KHSO4 K2SO4 CH3 N CH3 N Pyridine - Sulfur Trioxide Sulfur Trioxide - Oxone Complex Triethylamine Complex CAS RN: 37222-66-5 CAS RN: 26412-87-3 CAS RN: 761-01-3 B6158 250mg B6159 250mg 1g C2329 1g 5g

CH3

CH3 C CH3 Cl

O N N O N-Oxides N N O O 4-(tert-Butyl)pyridine 1-Oxide 4,4'-Bipyridine 1,1'-Dioxide 3-Chloropyridine N-Oxide CAS RN: 23569-17-7 CAS RN: 24573-15-7 CAS RN: 1851-22-5 C3416 1g D3219 5g D3220 1g 5g L0069 5g 25g M0981 25mL 500mL

N(CH3)2 CH3 O CN N

. xH O N Cl N Cl N 2 CH3 NCH3 O O O O O NMO 3-Cyanopyridine N-Oxide 2,6-Dichloropyridine N-Oxide DMAPO Hydrate 2,6-Lutidine N-Oxide (50% in Water, ca. 4.8mol/L) CAS RN: 14906-64-0 CAS RN: 2587-00-0 CAS RN: 1005-31-8 CAS RN: 1073-23-0 CAS RN: 7529-22-8 M2192 5g 25g P0557 25g 100g 500g P2775 250mg 1g T0466 25g 100g 500g T1362 1g 5g

CH3 O N CH3 CH3 . O N N CH3 N CH3 2H2O CH3 N CH3 O O O O NMO Pyridine N-Oxide 2-Phenylpyridine 1-Oxide TMANO Dihydrate TMANO Anhydrous CAS RN: 7529-22-8 CAS RN: 694-59-7 CAS RN: 1131-33-5 CAS RN: 62637-93-8 CAS RN: 1184-78-7 B0089 25g 100g 500g B0887 25g 500g T0061 25g 500g

O O O Cl Cl Other Oxidizing Agents Cl Cl O O O 1,4-Benzoquinone 1,4-Benzoquinone Chloranil CAS RN: 106-51-4 CAS RN: 106-51-4 CAS RN: 118-75-2 C1770 10mL D1070 25g 250g T1503 1g C0291 25g 100g 500g B0656 25g 100g 500g O (CH ) C C(CH ) Cl Cl O 3 3 3 3 NC Cl OOO O O O Cl Cl N N NC Cl O (CH3)3C C(CH3)3 Cl Br Chloranil (ca. 2% in N,N- O 3,3',5,5'-Tetra-tert-butyl- Dimethylformamide) DDQ 4,4'-diphenoquinone N-Chlorosuccinimide N-Bromosuccinimide CAS RN: 118-75-2 CAS RN: 84-58-2 CAS RN: 2455-14-3 CAS RN: 128-09-6 CAS RN: 128-08-5 D1265 25g 500g D3657 5g 25g T0620 25g 500g D1003 25g 500g B2152 5g 25g Br I O O O O O N N Cl Cl Cl O O N N N NNa CH3 CH3 N N N Br CH OON OON S CH3 3 I Br 1,3-Diiodo- Cl Cl O O DBDMH 5,5-dimethylhydantoin Trichloroisocyanuric Acid Sodium Dichloroisocyanurate N-Bromosaccharin CAS RN: 77-48-5 CAS RN: 2232-12-4 CAS RN: 87-90-1 CAS RN: 2893-78-9 CAS RN: 35812-01-2

H0395 25g 100g 500g D4413 1g 5g O0082 25g 100g 500g B2379 500g A0054 500mL O C H O O O O O Cl NOH HO N N OH Cl CH3 CH3 O O O O NHPI NDHPI Oxalyl Chloride Benzaldehyde Acetone CAS RN: 524-38-9 CAS RN: 57583-53-6 CAS RN: 79-37-8 CAS RN: 100-52-7 CAS RN: 67-64-1 B0306 25g D0798 25g 500g M2274 1g 5g M2321 1g 5g B2188 1g 5g O S O S N CH3 N CH O 3 C N N Cl CH3 S . CH . CH3 CH3 SO3 3 CH3 SO3 CH3 CH3 SCN CH3 1-Methyl-3-[6-(methylsulfinyl)- 1-Methyl-3-[6-(methylthio)- CH3 N hexyl]imidazolium hexyl]imidazolium N-tert-Butylphenylsulfinimidoyl 4-Benzoylpyridine Dimethyl Sulfoxide p-Toluenesulfonate p-Toluenesulfonate Chloride CAS RN: 14548-46-0 CAS RN: 67-68-5 CAS RN: 1352947-66-0 CAS RN: 1352947-63-7 CAS RN: 49591-20-0 B2240 1g 5g 25g C0075 25g 100g 500g C0076 25g 500g D0318 25g 100g 500g M1279 1g 5g 25g

CH3

SNHCCH3 SO2NCl SO2NCl CH O CH CH O O 3 Na Na Cl 3 2 CH3 S N CH3CH2 N S N C OCH3 . xH2O . 3H O Cl 2 O CH3CH2 O CH3 N-tert-Butylbenzenesulfenamide Chloramine B Hydrate Chloramine T Trihydrate Dichloramine T Burgess Reagent CAS RN: 19117-31-8 CAS RN: 304655-80-9 CAS RN: 7080-50-4 CAS RN: 473-34-7 CAS RN: 29684-56-8 T0077 5g 25g T3264 1g 5g C1806 50g 500g L0021 25g 500g P1910 25g 100g 500g

NC CN NC CN O . . (NH4)2Ce(NO3)6 CH3 C OPb 12MoO3 H3PO4 xH2O 4 NC CN NC CN Molybdo(VI)phosphoric TCNE TCNE (purified by sublimation) CAN LTA (contains Acetic Acid) Acid Hydrate CAS RN: 670-54-2 CAS RN: 670-54-2 CAS RN: 16774-21-3 CAS RN: 546-67-8 CAS RN: 51429-74-4 S0815 1g 5g T3651 5g 25g N0357 25mL 250mL I0604 25g 500g

CH (CH2)3CH3 3 O Ag2 CH (CH ) N (CH ) CH 3 2 3 2 3 3 NO3 CH3 C ONO I2 NCO 2 (CH2)3CH3 CH3 Picolinic Acid Silver(II) Salt Tetrabutylammonium Nitrate tert-Butyl Nitrite Iodine CAS RN: 14783-00-7 CAS RN: 1941-27-1 CAS RN: 540-80-7 CAS RN: 7553-56-2 H1404 200mg 1g 5g T1560 5g 25g M1197 1g 5g

OCH3

OH CH CH N 3 3 CH3 CH3 Catalysts for Oxidation CH3 N CH3 CH3 N CH3 O O 4-Methoxy-TEMPO Free AZADOL® TEMPO Free Radical Radical CAS RN: 1155843-79-0 CAS RN: 2564-83-2 CAS RN: 95407-69-5 A1348 5g 25g A2065 5g H0878 1g 5g I0908 100mg D4313 1g 5g O O O O O O O NH C CH3 HN C CH3 O C O2N O CH3 CH3

CH3 CH3 CH3 N CH3 CH3 CH3 N N NO2 CH3 CH3 I O BF CH3 N CH3 4 CH3 N CH3 CH3 N CH3 O 4-Acetamido-2,2,6,6- O O O2N 4-Acetamido-TEMPO Free tetramethyl-1-oxopiperidinium 4-Benzoyloxy-TEMPO Free 4-[2-[2-(4-Iodophenoxy)ethoxy]- Radical Tetrafluoroborate Radical carbonyl]benzoyloxy-2,2,6,6- DPPH Free Radical CAS RN: 14691-89-5 CAS RN: 219543-09-6 CAS RN: 3225-26-1 tetramethylpiperidin-1-oxyl CAS RN: 1898-66-4 I1117 100mg M2721 100mg T1559 1g 5g T1803 1g 5g O0308 10mL

O CH3 O

CH3O CH2CH2CH3 (CH2)3CH3 N CH3 O N I H O Fe3O4 P N N CH3CH2CH2 N CH2CH2CH3 RuO4 CH3(CH2)3 N (CH2)3CH3 ReO4 OsO O 4 I CH2CH2CH3 (CH2)3CH3 2-Iodo-N-isopropyl- Iodobenzene Catalyst Supported Tetrabutylammonium Osmium Tetroxide 5-methoxybenzamide on Magnetic Iron Oxide TPAP Perrhenate (4% in Water) CAS RN: 1820802-04-7 Nanoparticle (0.6-0.8mmol/g) CAS RN: 114615-82-6 CAS RN: 16385-59-4 CAS RN: 20816-12-0

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O0414 1g V0016 25g M0042 25g I0079 25g 100g 500g B2681 25g

CH3 CH CH3 CH3 3 O O O O CH3 O O Co OCH3 VO Mn . 2H2O Fe O H Os OH O Si N O OH O Fe3O4 O O O O Si C18H37 CH3 O O CH3 OCH3 CH3 2 CH3 2 CH3 3 2 Osmium Catalyst Manganese(II) supported on Magnetite Vanadyl Acetylacetonate Acetylacetonate Dihydrate Acetylacetone Iron(III) Salt Cobalt(II) Acetylacetonate (0.07-0.09mmol/g) CAS RN: 3153-26-2 CAS RN: 22033-51-8 CAS RN: 14024-18-1 CAS RN: 14024-48-7 C0373 25g 500g T0746 5g M0464 5g 25g A1424 1g 5g P2161 1g

CH3 CF3 CH3 O O O . . O O Co 2H2O Co xH2O Mo O O Pd2+ Pd2+ O O O CH3 C O CH C O 2 3 2 CH3 2 CH3 2 CH3 2 Cobalt(II) Acetylacetonate Cobalt(II) Molybdenum(VI)dioxy Dihydrate Trifluoroacetylacetonate Hydrate Acetylacetonate Palladium(II) Acetate Palladium(II) Acetate (Purified) CAS RN: 123334-29-2 CAS RN: 16092-38-9 CAS RN: 17524-05-9 CAS RN: 3375-31-3 CAS RN: 3375-31-3 P2106 1g 5g P1870 1g 5g S0318 25g 100g 500g B5613 1g 5g D1997 1g 5g

Cl O NN N N PRu Cl Pd2+ Co CH3 Mn CH3 [Pd(CH3COO)2]3 CF C O CH3 C O O C CH3 3 2 Cl O O CH3 CH3 3 CH3 C CH3 CH3 C CH3 CH3 CH3 Tris(triphenylphosphine)- Palladium(II) Acetate Trimer Palladium(II) Trifluoroacetate Salcomine (R,R)-Jacobsen's Catalyst ruthenium(II) Dichloride CAS RN: 53189-26-7 CAS RN: 42196-31-6 CAS RN: 14167-18-1 CAS RN: 138124-32-0 CAS RN: 15529-49-4

P1939 1g 5g C1944 100mg M1296 100mg

H3CCH3 H3C CH3 NO N N O Ru (CH3)3C O O C(CH3)3 KReO4 Cl CH3 Re O (CH3)3C C(CH3)3 O Chloronitrosyl[N,N'-bis(3,5-di-tert-butylsalicylidene)- Potassium Perrhenate 1,1,2,2-tetramethylethylenediaminato]ruthenium(IV) Methyltrioxorhenium(VII) CAS RN: 10466-65-6 CAS RN: 386761-71-3 CAS RN: 70197-13-6