108267-20-5

Basic information

• Product Name: (1S,2R)-2-aminocyclohexanol
• Synonyms: (1S,2R)-2-aminocyclohexanol;Cyclohexanol, 2-aMino-, (1S,2R)-
• CAS NO: 108267-20-5
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.175
• Mol File: 108267-20-5.mol
• Article Data: 68

Chemical Properties

• Boiling Point: 201℃
• Flash Point: 75℃
• Appearance: /
• Density: 1.037
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.94±0.40(Predicted)
• CAS DataBase Reference: (1S,2R)-2-aminocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-aminocyclohexanol(108267-20-5)
• EPA Substance Registry System: (1S,2R)-2-aminocyclohexanol(108267-20-5)

Safety Data

• Hazardous Substances Data: 108267-20-5(Hazardous Substances Data)

Usage

General Description

(1S,2R)-2-Aminocyclohexanol is a chemical compound that exists as a single stereoisomer and is a derivative of cyclohexane. It consists of a cyclohexane ring with an amino group and a hydroxyl group attached to it. (1S,2R)-2-Aminocyclohexanol is widely used in organic synthesis as a chiral building block for the preparation of various pharmaceuticals and agrochemicals. It also has potential applications in the production of certain types of polymers and surfactants. Additionally, (1S,2R)-2-Aminocyclohexanol has been investigated for its potential anti-inflammatory and anti-cancer properties, making it a subject of interest in the field of medicinal chemistry. Overall, this compound plays a significant role in the development of various chemical and pharmaceutical products.

Upstream product

• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 110716-78-4 (1R,2R)-trans-2-azidocyclohexanol 
• 98462-58-9 (1R,2R)-trans-2-[(R)-(α-methylbenzyl)amino]cyclohexanol 
• 286-20-4 cyclohexene oxide 
• 119479-49-1 (1S,2S)-trans-2-azidocyclohexanol 
• 221110-45-8 1-azido-2-(trimethylsiloxy)cyclohexane 
• 98361-56-9 (1S,2S)-trans-2-[(R)-(α-methylbenzyl)amino]cyclohexanol 
• 322407-34-1 (1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 2425-33-4 2-bromocyclocyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 28353-73-3 O-acetyl-2-cyclohexene-1-one oxime 
• 7480-30-0 trans-hexahydrobenzoxazol-2-one 
• 40571-86-6 rac-(1R,2R)-2-(benzylamino)cyclohexanol 

Downstream Products

• 18421-15-3 (±)-N-((1R,2R)-2-hydroxycyclohexyl)acetamide 
• 102176-62-5 optically inactive N,N'-bis-(trans-2-hydroxy-cyclohexyl)-adipamide 
• 102179-81-7 optically inactive N,N'-bis-(trans-2-hydroxy-cyclohexyl)-heptanediamide 
• 101591-07-5 (+/-)-N-benzyloxycarbonyl-N-methyl-glycine-(trans-2-hydroxy-cyclohexylamide) 
• 98428-55-8 (+/-)-(trans-2-hydroxy-cyclohexyl)-urea 
• 286-18-0 7-azabicyclo[4.1.0]heptane 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 
• 931-15-7 (1S,2S)-trans-2-aminocyclohexanol 
• 1437-81-6 (+/-)-sulfuric acid mono-(trans-2-amino-cyclohexyl ester) 
• 108881-46-5 (+/-)-N-(trans-2-hydroxy-cyclohexyl)-thiobenzamide 
• 92645-06-2 (+/-)-trans-2-(N-benzyloxycarbonyl)aminocyclohexanol 
• 88328-38-5 meso-N.N'-bis-(trans-2-hydroxy-cyclohexyl)-ethylenediamine 
• 88328-38-5 racem.-N.N'-bis-(trans-2-hydroxy-cyclohexyl)-ethylenediamine 
• 7432-60-2 trans-2-diethylaminocyclohexanol 

Relevant articles and documents

Synthesis and crystal structure of perhydro-1,4-benzoxazino[2,3-n]phenoxazine

The oxidation of trans-2-aminocyclohexanol with nitrobenzene in the presence of catalytic amounts of iron inter alia yields perhydro-1,4-benzoxazino[2,3-n]phenoxazine (1). This compound has been characterized analytically, spectroscopically and by X-ray diffraction. It is postulated that the oxidation of the 2-aminoalcohol leads to the intermediate formation of a 1,2-dione. The direct synthesis of 1 from trans-2-aminocyclohexanol and 1,2-cyclohexandione supports this hypothesis.

A NOVEL AND EFFICIENT SYNTHESIS OF (+)- AND (-)-TRANS-2-AMINOCYCLOHEXANOL BY ENZYMATIC HYDROLYSIS

Both enantiomers of trans-2-aminocyclohexanol were obtained by enzimatic hydrolysis of (+/-)-2-azidocyclohexanoates using lipases and subsequent hydrogenation.

Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water

Reduction of azides to amines and amides was carried out with NaBH4/CoCl2·6H2O in sole water at 25 °C under catalytic heterogeneous conditions. A broad spectrum of azides was reduced in a short time, chemoselectively in high yield and purity.

Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid

(S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(-)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81～>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.

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Enzymatic method of preparation of opticallly active trans-2-amino cyclohexanol derivatives

Supported Lipase Amano PS-D catalyzes the resolution of (±)-trans-2- tert butoxycarbonyl amino cyclohexanol by a selective acylation reaction. Using the supported enzyme gave a much faster reaction compared to existing methodology on similar substrates. A variety of acylating agents were investigated, with vinyl acetate providing the most practical and convenient procedure.

Method for synthesizing trans-cyclohexyldiamine

The invention discloses a method for synthesizing trans-cyclohexyldiamine. The method comprises the following steps: by using epoxy cyclohexane as the raw material, carrying out ring opening with ammonia water, adding sulfuric acid for dewatering and salification, adding free alkali, carrying out ring opening with ammonia water, and distilling to obtain the trans-cyclohexyldiamine. The method has the advantages of high repetitiveness of the synthesis route, and simple and accessible raw materials, and provides an alternative scheme for obtaining the trans-cyclohexyldiamine pure product.