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Fine Chemical Products Fine Chemical Products DOTTIKON EXCLUSIVE SYNTHESIS AG Your Specialist for Hazardous Reactions. DOTTIKON ES manufactures high-quality performance chemicals, intermediates and exclusive active pharmaceutical ingredients (APIs) for the world's leading chemical and pharmaceutical industry. The com- pany with its production site in Dottikon (Aargau, Switzerland) is specialized in hazardous reactions and is positioning itself as strategic development and manufacturing partner. Its safety culture created over the last 100 years guides innovative use of hazardous reactions, low-temperature and high-pressure chemis- try, as well as continuous processing. This shortens conventional chemical synthesis routes, increases yields, selectivities and purities, and reduces waste. The versatile technology and equipment portfolio is used to design, develop and optimize chemical processes, and scale up from kilograms to multi-tons. DOTTIKON ES' one-site strategy allows reduced decision and communication pathways. This ensures rapid and efficient project development as well as clear and transparent communication with customers. Broad process development experience and technological expertise enables us to offer high-quality chemicals and intermediates, including Amines Anilines Azaindoles Benzimidazoles Benzoic acid derivatives Benzyl compounds Boron building blocks Chiral compounds Cyclohexane derivatives Cyclopropyl building blocks Indazoles Indoles N-Heterocycles (various) Nitrate esters Nitroaromatic compounds O-Heterocycles (various) Phenols and anisoles Pyridine building blocks 3 Core Competencies Cross Coupling Reactions Suzuki-Miyaura Stille Heck Kumada Sonogashira Negishi Hazardous Reactions Azide chemistry (NaN3, organic azides such Methylation (Me2SO4, MeI) as DPPA) Nitration (see details below) Bromination (Br2, POBr3, PBr3, NBS) Nitroaldol reaction (MeNO2, EtNO2 ) Chlorination (Cl2, SOCl2, SO2Cl2, POCl3, Organometallic chemistry (Grignard, BuLi, PCl3, PCl5, NCS, oxalyl chloride, C2Cl6 ) HexLi, LDA, LiHMDS) Cyanation (NaCN, HCN [in-situ]) Oxidation (HNO3, KMnO4, mCPBA, DDQ, air, Diazotation (nitrous acid [HONO], ethyl diazo- H2O2, [t-BuO]2, peracids) acetate [EDA], Bestmann-Ohira reagent) Thiophosgenation (CSCl2) Hydrazine chemistry (NH2NH2, alkylhydrazines) Miscellaneous (EDA (Ethyl diazoacetate), Epich- Hydride reduction (LiAlH4, AIH2R2, BH3, lorohydrine, P2O5, HOBT (hydroxybenzotriazole), + Na [H3BCN]-, NaH, NaBH4) DIAD (diisopropylazodicarboxylate)) Iodination (I2, NaI) Heterocycle Synthesis Benzimidazoles Isoquinolines and quinolines Benzofuranes Purine analogs Indazoles and indoles Triazoles and tetrazoles High-pressure Chemistry Catalytic hydrogenation Carbon monoxide/dioxide Heterogeneous (screenings of >400 catalysts) Hydroformylation Homogeneous H2, CO, CO2, NO, NH3, HNR2 Enantioselective Low-temperature Chemistry Metalorganic transformations Boronic acid synthesis Selective oxidations and hydrogenations Cryogenic quenching Nitration Aromatic nitration (conc. HNO3, HNO3/H2SO4, glacial HNO3/AcOH) Continuous nitration technology Nitrate ester formation Separation and Drying under cGMP Stereoisomer separation by fractionated crystallization Filtration and centrifugation on all scales 3 Distillation (0.1–50 m ; columns up to 80 theoretical plates) 3 Drying on large scale (up to 6 m ) 4 More than 100 Reactions on Large Scale Typical Reactions Alkoxylation Nef reaction Alkylation Nitration Aromatic substitution Optical resolution Baeyer-Villiger oxidation ortho-Directed metallation Beckmann rearrangement Oxidation Benzidine rearrangement Oxime formation Boronic acid synthesis Phase-transfer reactions Cannizzaro reaction Pictet-Spengler reaction Carbamoylation Pinner reaction Chiral chemistry Reduction Chlorosulfonation Reductive coupling Claisen condensation Reductive cyclization Cross coupling Robinson annulation Curtius rearrangement Rosenmund reduction Cycloaddition Sandmeyer reaction Cyclocondensation Schiff-base reduction Darzens synthesis Schotten-Baumann reaction Dealkylation Skraup synthesis Decarboxylation Solid acid catalysis Dehalogenation Strecker synthesis Diazonium chemistry Substitution reactions Dieckmann condensation Sulfonation Diels-Alder reaction Sulfoxidation Doebner-Knoevenagel Tosylation condensation Transesterification Enantioselective reactions Ullmann coupling Epoxidation Vilsmeier-Haack reaction Esterification Wacker oxidation Ether formation Wittig reaction Finkelstein reaction Wohl-Ziegler reactions Indole synthesis ... Formylation Gabriel synthesis Halide exchange Halogenation Hemetsberger reaction Hofmann rearrangement Hydrolysis Hydrogenation Hydrosilylation Isomerization Ketalization Liquid-ammonia reactions Lithiation Mannich reaction Mesylation Metal complexation Methylation Michael addition Mitsunobu reaction 5 Content Product Groups 8–9 Products 10–50 Index, Chemical Formula 52 Index, Registry Number 53–54 Index, Parent Name 55–60 The copyright of any content (text, illustration and pictures) in this catalog is owned by DOTTIKON ES HOLDING AG. Unauthorized reproduction of any content is prohibited by Federal law and subject to criminal prosecution. 7 Product Groups Structure Product Group Name Page Amines 10−12 piperidines, piperazines, N H aliphatic amines NH2 Anilines 13−15 Azaindoles 16 N N H N Benzimidazoles 17 N H CO H 2 Benzoic Acid Derivatives 18−21 Benzyl Compounds 22−23 X Boron Building Blocks 24 R B(OH)2 a Chiral Compounds 25–28 d b c O Cyclohexane Derivatives 29–31 cyclohexanones, cyclohexane R carboxylic acids and alcohols Cyclopropyl Building Blocks 32 X 8 Product Groups Structure Product Group Name Page Indazoles 33 N N H Indoles 34–37 N H H N O N-Heterocycles (various) 38–40 NH benzotriazoles, imidazoles, isoquinolines, quinolines, quinoxalines, tetrazoles, triazoles O O2NO H O Nitrate Esters 41 O H ONO2 NO2 Nitroaromatic Compounds 42–43 O-Heterocycles (various) 44 benzodioxanes, benzodioxoles, O isosorbide derivatives OR Phenols and Anisoles 45–46 Pyridine Building Blocks 47–48 N O Various Compounds 49–50 OEt C N 9 Product Amines (1/3) Structure Product Name CAS cis-1-Amino-2,6-dimethylpiperidine 61147-58-8 (Z)-N-Amino-2,6-dimethylpiperidine N NH2 6-Amino-1-hexanol 4048-33-3 NH HO 2 Aminomalonic acid diethyl ester hydrochloride 13433-00-6 EtO C CO Et 2 2 Diethyl aminomalonate hydrochloride NH2 · HCl 2-(Aminomethyl)-1-ethylpyrrolidine 26116-12-1 NH 2 N-Ethyl-2-aminomethylpyrrolidine N 2-(Aminomethyl)piperidine 22990-77-8 2-Piperidinemethylamine NH N 2 H 2-(4-Aminophenyl)acetonitrile 3544-25-0 CN 4-Aminophenylacetonitrile H2N 1-Aminopiperidine 2213-43-6 1-Piperidinamine N NH2 1-Benzylpiperazine 2759-28-6 N HN 10 Product Amines (2/3) Structure Product Name CAS 1-Benzyl-4-piperidinamine 50541-93-0 N 4-Amino-1-benzylpiperidine H2N 4-Benzylpiperidine 31252-42-3 HN O 1-Boc-azetidin-3-one 398489-26-4 tert-Butyl 3-oxoazetidine-1-carboxylate N O N-Boc-azetidin-3-one O 1,4-Diazabicyclo[3.2.2]nonane dihydrochloride 150208-70-1 NH N · 2 HCl NH2 2,3-Dimethylcyclohexylamine 42195-92-6 2,3-Dimethylcyclohexanamine cis-2,6-Dimethylpiperidine 766-17-6 N H 3,5-Dimethylpiperidine 35794-11-7 3,5-Lupetidine N (cis:trans ≈ 83:17) H Isopropylhydrazine hydrochloride 16726-41-3 NH . HCl N 2 H 11 Product Amines (3/3) Structure Product Name CAS 1-Methyl-3-phenylpropylamine 22374-89-6 4-Phenyl-2-butylamine NH2 O 1-(Tetrahydro-2-furoyl)piperazine 63074-07-7 THF-Piperazine N HN O COOH DL-m-Tyrosine 775-06-4 3-(3-Hydroxyphenyl)-DL-alanine NH2 OH 12 Product Anilines (1/3) Structure Product Name CAS O 4-Aminoacetophenone 99-92-3 1-(4-Aminophenyl)ethanone 4-Acetylaniline NH2 5(6)-Amino-1-(4-aminophenyl)-1,3,3-trimethylindane 68170-20-7 5/6,4‘-Diamino-1,3,3,3-trimethyl-1-phenylindane H2N NH2 N 4-Amino-N-ethyl-N-isopropylaniline hydrochloride 91215-79-1 N-Ethyl-N-isopropyl-para-phenylenediamine hydrochloride NH2 · HCl CHO 3-Amino-4-methoxybenzaldehyde 351003-10-6 NH2 OMe CN 2-Amino-6-methylbenzonitrile 56043-01-7 NH2 O N-(3-Amino-2-methylphenyl)acetamide 65999-76-0 HN 3-Amino-2-methylacetanilide NH2 NH 2 4-sec-Butylaniline 30273-11-1 NH 2 1,3-Diamino-4,6-diisopropylbenzene 3102-71-4 4,6-Bis-(1-methylethyl)-1,3-benzenediamine NH2 13 Product Anilines (2/3) Structure Product Name CAS NH2 2,4-Diamino-1,3,5-trimethylbenzene 3102-70-3 2,4-Diaminomesitylene 2,4,6-Trimethyl-meta-phenylenediamine NH2 NH2 3,4-Dimethoxyaniline 6315-89-5 4-Aminocatechol dimethyl ether OMe OMe NH2 Dodecylaniline 68411-48-3 (branched, mixture of isomers) C12H25 NH2 2-Ethylaniline 578-54-1 NH 2 4-Ethylaniline 589-16-2 NH2 4-Methoxy-2-methylaniline 102-50-1 2-Methyl-para-anisidine OMe NH2 4-Methoxy-3-nitroaniline 577-72-0 3-Nitro-para-anisidine NO2 OMe NH2 3-Methyl-1,2-benzenediamine 2687-25-4 NH2 2,3-Diaminotoluene (30% or 50% in toluene) 14 Product Anilines (3/3) Structure Product Name CAS NH2 2-Methyl-3-nitroaniline 603-83-8 3-Nitro-ortho-toluidine NO2 NH2 2-Methyl-6-nitroaniline 570-24-1 O2N 6-Nitro-ortho-toluidine NH 2 2,3,5,6-Tetramethyl-1,4-benzenediamine 3102-87-2 3,6-Diaminodurene 2,3,5,6-Tetramethyl-para-phenylenediamine NH2 NH2 2,4,6-Trimethylaniline 88-05-1 Mesidine 15 Product Azaindoles Structure Product Name CAS N 4-Azaindole-2-carboxylic acid methyl ester 394223-19-9 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid methyl ester CO2Me N H Cl 4-Chloro-5-azaindole-2-carboxylic acid methyl ester 688357-19-9 N 4-Chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester CO2Me N H Cl 4-Chloro-7-azaindole-2-carboxylic
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