6850-38-0

Basic information

• Product Name: 2-Aminocyclohexanol
• Synonyms: aminocyclohexanol;2-Aminocyclohenxanol;2-Aminocyclohexanol 98%;2-Aminocyclohexanol98%;1-Amino-2-hydroxycyclohexane;2-Aminocyclohexanol (cis- and trans- mixture);2-Aminocyclohexanol;2-Aminocyclohexan-1-ol 98%
• CAS NO: 6850-38-0
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• Mol File: 6850-38-0.mol
• Article Data: 69

Chemical Properties

• Melting Point: 65 °C
• Boiling Point: 201.1 °C at 760 mmHg
• Flash Point: 75.4 °C
• Appearance: /
• Density: 1.037 g/cm³
• Storage Temp.: 0-10°C
• Solubility: soluble in Methanol
• PKA: 14.94±0.40(Predicted)
• CAS DataBase Reference: 2-Aminocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminocyclohexanol(6850-38-0)
• EPA Substance Registry System: 2-Aminocyclohexanol(6850-38-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 34-22
• Safety Statements: 26-36/37/39
• RIDADR: 3259
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6850-38-0(Hazardous Substances Data)

Usage

Chemical Properties

White to Light orange to Yellow powder to crystal.

Uses

Trans-2-aminocyclohexanol and cis-/trans-1,2-cyclohexanediamines have found their application in the synthesis of the antiarrhythmic medicament vernakalant and spleen tyrosine kinase inhibitor, κ-opioid analgesics.

Preparation

2-Aminocyclohexanol Synthesis: Under water bath reaction conditions, 214.3 g of ammonia water was added to a 500 mL three-necked flask. Stir and heat, and when the internal temperature reaches about 50°C, start to slowly drop 50.0 g of 1,2-epoxycyclohexane into the reaction flask. After the dropwise addition was completed, the reaction was performed at a constant temperature for 12h. After the reaction was completed, the reaction was processed to obtain a crude product, which was purified by recrystallization to obtain 2-aminocyclohexanol with a yield of 90% and an amine value (mgKOH/g) of 453.

InChI:InChI=1/C6H13NO/c7-5-3-1-2-4-6(5)8/h5-6,8H,1-4,7H2

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 40571-86-6 rac-(1R,2R)-2-(benzylamino)cyclohexanol 
• 882409-01-0 (S)-mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol 
• 141553-09-5 (1R,2R)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 119479-49-1 (1S,2S)-trans-2-azidocyclohexanol 
• 155975-21-6 (1S,2S)-2-(t-butoxycarbonylamino)cyclohexyl acetate 
• 882409-00-9 (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol 
• 1541-25-9 3-amino-1-cyclohexene 
• 28353-73-3 O-acetyl-2-cyclohexene-1-one oxime 
• 7480-30-0 trans-hexahydrobenzoxazol-2-one 
• 108-93-0 cyclohexanol 
• 5456-63-3 trans-2-aminocyclohexanol hydrochloride 
• 2425-33-4 2-bromocyclocyclohexanol 
• 6628-80-4 trans-2-chlorocyclohexanol 

Downstream Products

• 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) 
• 92645-06-2 (+/-)-trans-2-(N-benzyloxycarbonyl)aminocyclohexanol 
• 101260-08-6 optically inactive N,N'-bis-(trans-2-hydroxy-cyclohexyl)-malonamide 
• 138036-49-4 (1α,2β)-2-(2,2,2-trifluoro-1,1-diphenylethylsulfenyl)aminocyclohexan-1-ol 
• 91390-37-3 N-(2-fluoroethyl)-N'-(cis-2-hydroxycyclohexyl)-N-nitrosourea 
• 51925-38-3 (1SR,2SR)-2-n-butylaminocyclohexanol 
• 7432-60-2 trans-2-diethylaminocyclohexanol 
• 35357-98-3 2-(dipropylamino)cyclohexanol 
• 69592-28-5 trans-2-(isopropylamino)cyclohexan-1-ol 

Relevant articles and documents

One-pot production of phenazine from lignin-derived catechol

Upgrading lignin-derived monomeric products is crucial in bio-refineries to effectively utilize lignin. Herein, we report a simple strategy to convert catechol to phenazine, a useful N-heterocycle three-aromatic-ring compound, whose current synthetic procedure is complex via a petroleum-derived feedstock. The reaction uses catechol as the sole carbon source and aqueous ammonia as reaction media and a nitrogen source. Without additional solvents, phenazine was obtained in 67% yield in the form of high purity crystals (>97%) over a Pd/C catalyst after a one-pot-two-stage reaction. When cyclohexane was used as a co-solvent in the first step, a higher yield (81%) and purity (>99%) were achieved. Mechanistic investigations involving control experiments and an isotope labeling study reveal that hydrogenation, amination, coupling and dehydrogenation reactions are the key steps leading to phenazine formation. The conversion of other lignin-derived catechols highlights that the protocol is extendable to produce substituted phenazines.

Asymmetric amination of meso-epoxide with vegetable powder as a low-toxicity catalyst

This paper describes the scope and limitation of substrates subjected to asymmetric amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening commercially available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals.

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.