721884-81-7

Basic information

• Product Name: (1S,3S)-3-AMINOCYCLOHEXANOL
• Synonyms: Trans-(3S,4S)-3-aMino-cyclohexanol hydrochloride;Cyclohexanol, 3-amino-, (1S,3S)-;(1S,3S)
• CAS NO: 721884-81-7
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17352
• Mol File: 721884-81-7.mol

Chemical Properties

• Melting Point: 70.6-70.9 °C
• Boiling Point: 201.1±33.0 °C(Predicted)
• Appearance: /
• Density: 1.037±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.09±0.40(Predicted)
• CAS DataBase Reference: (1S,3S)-3-AMINOCYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S)-3-AMINOCYCLOHEXANOL(721884-81-7)
• EPA Substance Registry System: (1S,3S)-3-AMINOCYCLOHEXANOL(721884-81-7)

Safety Data

• Hazardous Substances Data: 721884-81-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(1S,3S)-3-Aminocyclohexanol is utilized as a key intermediate in the synthesis of various pharmaceuticals, leveraging its unique structural features to construct complex organic molecules with potential therapeutic applications.
Used in Asymmetric Synthesis:
Owing to its chiral nature, (1S,3S)-3-Aminocyclohexanol serves as a valuable component in asymmetric synthesis, enabling the production of enantiomerically pure compounds, which is crucial for the development of drugs with specific biological activities.
Used in Metal-Catalyzed Asymmetric Reactions:
(1S,3S)-3-Aminocyclohexanol is explored for its potential as a ligand in metal-catalyzed asymmetric reactions, where it can influence the selectivity and efficiency of these processes, contributing to the advancement of catalytic methodologies in organic chemistry.
Used in Organic Chemistry Research:
As a versatile chemical, (1S,3S)-3-Aminocyclohexanol is employed in research settings to study and develop new synthetic pathways, reaction mechanisms, and applications in organic chemistry, thereby expanding the horizons of chemical knowledge and innovation.

Upstream product

• 750649-39-9 (+/-)-trans-(3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 750649-39-9 ((1S,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 1257303-70-0 (1S,3S)-(3-hydroxycyclohexyl)ammonium (R)-mandelate 
• 13941-94-1 (rac)-trans-1-(3-hydroxycyclohexyl)benzamide 
• 6850-39-1 3-aminocyclohexanol 

Downstream Products

• 1397712-48-9 (1S,3S)-3-(6,6-dimethyl-4,4-dioxo-5-phenyl-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-ylamino)cyclohexanol 
• 1439358-23-2 C₁₉H₂₄N₄O₄S 
• 1146615-90-8 (1S,3S)-3-(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol 

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.

2-Substituted-1H-benz(de)-isoquinoline-1,3-(2H)-diones

Compounds of the following formula STR1 wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, and trifluoromethyl, and R is selected from a triacetyl substituted pentose, pentose, a tetraacetyl substituted hexose, hexose, a hydroxy substituted cycloalkyl of 5 to 7 carbons, STR2 wherein n is 1 or 2 and R3 is hydrogen, an alkali metal or alkaline earth metal ion; are disclosed. These compounds possess useful anti-inflammatory activity.