6850-39-1

Basic information

• Product Name: 3-Aminocyclohexanol
• Synonyms: 3-Aminocyclohexanol;3-Amino-cyclohexanol(mixture of cis-and trans-);3-AMinocyclohexanol (cis/trans Mixture);3-aMinocyclohexan-1-ol;3-AMino-cyclohexano.HCl;3-AMinocyclohexanol hcl;3-aMinocyclohexanol hydrochloride;1-Amino-3-hydroxycyclohexane, 3-Hydroxycyclohexan-1-amine
• CAS NO: 6850-39-1
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• Product Categories: pharmacetical;Amines;Intermediates;Miscellaneous Reagents
• Mol File: 6850-39-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 64-69°C
• Boiling Point: 201.1 °C at 760 mmHg
• Flash Point: 75.4 °C
• Appearance: /
• Density: 1.037 g/cm³
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform, Dichloromethane, Dichloro Sulfoxide, Methanol
• PKA: 15.09±0.40(Predicted)
• CAS DataBase Reference: 3-Aminocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminocyclohexanol(6850-39-1)
• EPA Substance Registry System: 3-Aminocyclohexanol(6850-39-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 6850-39-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to Pale Pink Solid

Upstream product

• 621-42-1 meta-hydroxyacetanilide 
• 764-59-0 hex-5-en-1-al 
• 177366-86-8 N-<1-(Trimethylsiloxy)hex-5-enyl>formamide 
• 591-27-5 m-Hydroxyaniline 
• 106729-79-7 (+/-)-cis-2-(3-hydroxycyclohexyl)isoindole-1,3-dione 
• 5220-49-5 3-amino-cyclohex-2-enone 
• 13941-94-1 (rac)-trans-1-(3-hydroxycyclohexyl)benzamide 
• 57376-99-5 (+/-)-N-(cis-3-hydroxy-cyclohexyl)-acetamide 

Downstream Products

• 764-59-0 hex-5-en-1-al 
• 91470-37-0 2-oxa-4-aza-bicyclo[3.3.1]nonan-3-one 
• 15676-77-4 trans-3-Tritylamino-cyclohexanol 
• 15676-77-4 cis-3-Tritylamino-cyclohexanol 
• 23074-07-9 1-{[4-[2-(5-chloro-2-methoxybenzamido)ethyl]phenyl]sulfonyl}-3-(trans-3-hydroxycyclohexyl)urea 
• 23074-07-9 1-{[4-[2-(5-chloro-2-methoxybenzamido)ethyl]phenyl]sulfonyl}-3-(cis-3-hydroxycyclohexyl)urea 
• 721884-82-8 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide 
• 13941-94-1 (R,R)-3-benzylamidocyclohexanol 
• 721884-81-7 (1S,3S)-3-aminocyclohexanol 
• 721884-88-4 (R,R)-3-benzylaminocyclohexanol 
• 1257303-73-3 (1R,3R)-(3-hydroxycyclohexyl)ammonium (S)-mandelate 
• 1257303-70-0 (1S,3S)-(3-hydroxycyclohexyl)ammonium (R)-mandelate 
• 750649-39-9 ((1R,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 750649-39-9 ((1S,3R)-3-hydroxycyclohexyl)carbamic acid benzyl ester 

Relevant articles and documents

Diastereoisomeric salt formation and enzyme-catalyzed kinetic resolution as complementary methods for the chiral separation of cis-/trans-enantiomers of 3-aminocyclohexanol

This contribution demonstrates the preparative-scale synthesis of (1S,3S)-3-aminocyclohexanol by either enzymatic kinetic resolution of Cbz-protected 3-aminocyclohexanols or direct diastereoisomeric salt formation with (R)-mandelic acid. The salt formation demonstrates how a single enantiomer, (1S,3S)-3-aminocyclohexanol (R)-mandelate, can be effectively isolated from the cis/trans racemic mixture and subsequently converted to the free amine, (1S,3S)-3-aminocyclohexanol, by ion-exchange chromatography. We have also demonstrated how the other three enantiomers of 3-aminocyclohexanol can be prepared by either diastereoisomeric salt formation or enzymatic kinetic resolution.

Resolution of trans-3-aminocyclohexanol

(R,R)- and (S,S)-trans-3-Aminocyclohexanol were prepared via an enzymatic resolution of (±)-trans-1-acetoxy-3-benzylamido-cyclohexane with >95% enantiomeric excess.

Convenient Procedure for the Reduction of β-Enamino Ketones: Synthesis of γ-Amino Alcohols and Tetrahydro-1,3-oxazines

γ-Amino alcohols 3 can be easily synthesized in very good yields by reduction of enaminones 1 with Na in PrOH-tetrahydrofuran.The reaction is fast, easy to perform, inexpensive and the easily accesible starting materials provide a convenient entry to γ-amino alcohols.The relative configuration assignment of the diastereomeric γ-amino alcohols obtained has been established by 1H and 13C NMR studies and unequivocally assigned by their cyclic tetrahydro-1,3-oxazine derivatives 4.