32958-55-7

Basic information

• Product Name: (trans)-3,3,5-trimethylcyclohexylamine
• Synonyms: (trans)-3,3,5-trimethylcyclohexylamine;Einecs 251-308-9
• CAS NO: 32958-55-7
• Molecular Formula: C₉H₁₉N
• Molecular Weight: 141.25386
• EINECS: 251-308-9
• Mol File: 32958-55-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 172.2°Cat760mmHg
• Flash Point: 32.9°C
• Appearance: /
• Density: 0.819g/cm³
• Vapor Pressure: 1.35mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: (trans)-3,3,5-trimethylcyclohexylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (trans)-3,3,5-trimethylcyclohexylamine(32958-55-7)
• EPA Substance Registry System: (trans)-3,3,5-trimethylcyclohexylamine(32958-55-7)

Safety Data

• Hazardous Substances Data: 32958-55-7(Hazardous Substances Data)

Usage

Description

(trans)-3,3,5-trimethylcyclohexylamine, with the molecular formula C9H19N, is a tertiary amine characterized by three alkyl groups attached to the nitrogen atom. This chemical compound features a bicyclic structure with three methyl groups on the cyclohexyl ring, which contributes to its unique steric hindrance and bulkiness.

Uses

Used in Pharmaceutical Synthesis:
(trans)-3,3,5-trimethylcyclohexylamine is utilized as a key building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique structure and chemical properties make it a valuable component in the development of new drugs and chemicals.
Used in Organic Synthesis:
As a versatile reagent, (trans)-3,3,5-trimethylcyclohexylamine is employed in organic synthesis to facilitate the creation of a wide range of chemical products. Its steric properties and reactivity contribute to its effectiveness in this application.
Used as a Chiral Resolving Agent in Chromatography:
(trans)-3,3,5-trimethylcyclohexylamine's unique structure also makes it suitable for use as a chiral resolving agent in chromatography, a technique used to separate enantiomers or optical isomers of chiral molecules.
Used in Corrosion Inhibition:
Studies have explored the potential of (trans)-3,3,5-trimethylcyclohexylamine for use in corrosion inhibition, where it could be applied to protect materials from the damaging effects of corrosion.
Used as a Stabilizer in Polymer Production:
Additionally, (trans)-3,3,5-trimethylcyclohexylamine has been investigated for its potential use as a stabilizer in the production of polymers, enhancing the stability and quality of the final product.

InChI:InChI=1/C9H19N/c1-7-4-8(10)6-9(2,3)5-7/h7-8H,4-6,10H2,1-3H3

Upstream product

• 37690-43-0 trans-3.3.5-Trimethylcyclohexanol-tosylat 
• 37694-11-4 3,3,5-trimethylcyclohexanone oxime 
• 134734-56-8 (E)-O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime 
• 2157-58-6 3,5,5-trimethyl-cyclohex-2-enone oxime 
• 37690-43-0 (+/-)-toluene-4-sulfonic acid-(3,3,5c-trimethyl-cyclohex-r-yl ester) 

Downstream Products

• 1803274-65-8 3-(2-{[4-(trifluoromethoxy)phenyl]amino}-1-[(1R,5R)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-5-yl)propanoic acid 

Relevant articles and documents

SYNTHESIS AND REACTIONS OF α,β-UNSATURATED AMINES AND THEIR DERIVATIVES. PART VI. ACTION OF DIBORANE ON O-ACETYL 3,5,5-TRIMETHYL-2-CYCLOHEXENE-1-ONE OXIME

The reaction of diborane with O-acetyl 3,5,5-trimethyl-2-cyclohexene-1-one oxime (1) has been examined.The effect of the temperature, molar ratio of substrates and O-acetyl oxime configuration on the stoichiometry and direction of the reaction is described.

Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen ? Systems with Hydride Reagents

Reductions of 3- and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH4, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (i.e., acetoxyboranes) attack preferentially from the equatorial side.This is in direct contrast to the results observed for the same reagents with the corresponding ketones and is interpreted as implying that additional steric interactions induced by the nitrogen substituents encumber axial attack by substituted hydride reagents and force approach from the equatorial direction.The very bulky tri-sec-butylborohydride anion affords highly stereodiscriminating equatorial attack.Reductions of 2-alkylcyclohexyl and 2-alkylcyclopentyl imines and enamines also proceed with high stereoselectivity to give cis-2-alkyl cyclic amines with both hindered and unhindered reagents.This is interpreted to be the result of (1) augmented steric interactions between nitrogen substituents and equatorial 2-alkyl groups (1,3-allylic strain) which induces conformational changes to favor the axial 2-alkyl conformer and (2) hindrance toward equatorial approach by reagents induced by axial alkyl substituents.The result is that equatorial approach is favored with equatorial 2-alkyl conformers and preferential axial approach with axial 2-alkyl conformers, leading to stereoselective production of cis-2-alkylamines. trans-2-n-Propyl-4-tert-butylcyclohexanone is reduced by LiBH(sec-Bu)3 preferentially from the axial direction in contrast to the usual highly selective equatorial attack observed with other cyclohexanones.