2163-33-9

Basic information

• Product Name: 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS
• Synonyms: 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS;CIS-1-AMINO-4-TERT-BUTYLCYCLOHEXANE;CIS-4-TERT-BUTYL-1-CYCLOHEXANAMINE;CYCLOHEXANAMINE, 4-(1,1-DIMETHYLETHYL)-, CIS-;Cis-1-Amino-4-tert-butylcyclohexylamine;Cis-1-Amino-4-Tert-Butylcyclohexane(WXC00783)
• CAS NO: 2163-33-9
• Molecular Formula: C₁₀H₂₁N
• Molecular Weight: 155.28
• Mol File: 2163-33-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 197.953 °C at 760 mmHg
• Flash Point: 51.316 °C
• Appearance: /
• Density: 0.861 g/cm³
• Vapor Pressure: 0.369mmHg at 25°C
• Refractive Index: 1.46
• PKA: 10.58±0.70(Predicted)
• CAS DataBase Reference: 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS(2163-33-9)
• EPA Substance Registry System: 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS(2163-33-9)

Safety Data

• Hazardous Substances Data: 2163-33-9(Hazardous Substances Data)

Usage

General Description

4-TERT-BUTYLCYCLOHEXYLAMINE, CIS is a chemical compound with the molecular formula C10H21N. It is an organic compound with a cyclohexylamine backbone and a tert-butyl group attached to the carbon atom. The "cis" designation indicates that the tert-butyl and cyclohexyl groups are oriented on the same side of the amine functional group. 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS is used as a building block in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and specialty chemicals. It is also used as a stabilizer in the manufacture of polymers and plastics. 4-TERT-BUTYLCYCLOHEXYLAMINE, CIS is a colorless liquid with a faint odor and is considered to be relatively stable under normal storage and handling conditions.

InChI:InChI=1/C10H21N/c1-10(2,3)8-4-6-9(11)7-5-8/h8-9H,4-7,11H2,1-3H3/t8-,9+

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 98-54-4 para-tert-butylphenol 
• 67498-84-4 cis-N-benzyl-4-tert-butylcyclohexylamine 
• 344869-42-7 N-(4-tert-butylcyclohexyl)benzylamine 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 943-27-1 4'-t-butylacetophenone 
• 4701-98-8 4-tert-butylcyclohexanone oxime 
• 943-28-2 cis-4-t-butylcyclohexanecarboxylic acid 

Downstream Products

• 2523-68-4 cis-4-t-butyl-N,N-dimethylcyclohexylamine 
• 101866-18-6 2-[(cis-4-tert-Butyl-cyclohexylimino)-methyl]-phenol 
• 52755-77-8 N-(cis-4-tert.-Butylcyclohexyl)-sulfinylamin 
• 67282-90-0 trans-N-(4-tert-butylcyclohexyl)pyrrolidine 
• 61925-69-7 N-(4-tert-Butyl-cyclohexyl)-3,3-diphenyl-propionamide 

Relevant articles and documents

Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates

The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).

Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines

Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.

Aliphatic C-H Bond Oxidation with Hydrogen Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through Torsional Effects

Substituted N-cyclohexyl amides undergo aliphatic C-H bond oxidation with H2O2 catalyzed by manganese complexes. The reactions are directed by torsional effects leading to site-selective oxidation of cis-1,4-, trans-1,3-, and cis-1,2-cyclohexanediamides. The corresponding diastereoisomers are unreactive under the same conditions. Competitive oxidation of cis-trans mixtures of 4-substituted N-cyclohexylamides leads to quantitative conversion of the cis-isomers, allowing isolation and successive conversion of the trans-isomers into densely functionalized oxidation products with excellent site selectivity and good enantioselectivity.