2-Isopropyl-5-methylcyclohexanamine

Base Information

• Chemical Name: 2-Isopropyl-5-methylcyclohexanamine
• CAS No.: 21411-81-4
• Molecular Formula: C10H21 N
• Molecular Weight: 155.283
• Hs Code.: 2921300090
• European Community (EC) Number: 244-377-1
• NSC Number: 243755
• UNII: ZRS6GYG67V
• DSSTox Substance ID: DTXSID20903120
• Nikkaji Number: J226.200B
• Mol file: 21411-81-4.mol

Synonyms:2-Isopropyl-5-methylcyclohexanamine;21411-81-4;Menthylamine;Neomenthylamine;5-methyl-2-(propan-2-yl)cyclohexan-1-amine;5-methyl-2-propan-2-ylcyclohexan-1-amine;ZRS6GYG67V;L-Menthylamine;L-MENTHYLAMINE, TECH. 85;EINECS 218-693-5;2-(Isopropyl)-5-methylcyclohexylamine;NSC-243755;(1R, 2R, 5S)-NEOMENTHYL AMINE;51743-63-6;menthylamin;(1R-(1alpha,2beta,5alpha))-2-(Isopropyl)-5-methylcyclohexylamine;7231-40-5;NoName_3716;Maybridge3_000691;UNII-ZRS6GYG67V;Cyclohexanamine, 5-methyl-2-(1-methylethyl)-;(1R,2R,5S)-Neomenthylamine;[1R-(1alpha,2Beta,5alpha)]-2-(isopropyl)-5-methylcyclohexylamine;SCHEMBL1659593;DTXSID20903120;Cyclohexanamine, 5-methyl-2-(1-methylethyl)-, (1R-(1alpha,2beta,5alpha))-;p-Menthan-3-amine, trans-1,4-;2-Isopropyl-5-methylcyclohexylamine;NSC 7325;EINECS 244-377-1;MFCD00038549;NSC243755;2-Isopropyl-5-methylcyclohexanamine #;AKOS000133718;AKOS016900963;NSC 243755;SB31034;SB37452;SB45643;IDI1_012078;5-Methyl-2-(1-methylethyl)cyclohexanamine;FT-0612710;FT-0679680;FT-0771282;EN300-37524;J-010529;Z239626690;Cyclohexanamine, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.alpha.,5.beta.)-

Chemical Property of 2-Isopropyl-5-methylcyclohexanamine

Chemical Property:

• Boiling Point: 192.8°Cat760mmHg
• Flash Point: 45.8°C
• PSA: 26.02000
• Density: 0.834g/cm³
• LogP: 3.10620
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 155.167399674
• Heavy Atom Count: 11
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

5-methyl-2-(propan-2-yl)cyclohexan-1-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)N)C(C)C
• General Description: L-Menthylamine, Tech. 85, is an optically active amine derived from the reductive amination of l-menthol with aliphatic nitriles, yielding a mixture of stereoisomers including menthylamine, neomenthylamine, isomenthylamine, and neoisomenthylamine in varying ratios (54:24:17:5). The reaction employs a copper-alumina catalyst modified with lithium hydroxide under controlled conditions, demonstrating selectivity for specific N-alkyl derivatives. L-MENTHYLAMINE, TECH. 85 is also known by alternative names such as p-Menthan-3-amine and NSC 243755.

Technology Process of 2-Isopropyl-5-methylcyclohexanamine

There total 20 articles about 2-Isopropyl-5-methylcyclohexanamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

DL-neomenthol (490-99-3,491-01-0,491-02-1,1490-04-6,2216-51-5,2216-52-6,3623-51-6,3623-52-7,3623-53-8,15356-60-2,15356-70-4,20747-49-3,20752-33-4,20752-34-5,23283-97-8,64282-88-8,89-78-1) → rac-menthylamine (2216-54-8,4894-99-9,7231-40-5,16934-77-3,20706-69-8,20706-70-1,21411-81-4,23399-21-5,51743-63-6,66609-74-3,85549-06-0,787534-09-2)

Guidance literature:

DL-neomenthol; With 1-methyl-1H-imidazole; methanesulfonyl chloride; triethylamine; In toluene; at 20 ℃; for 2h;

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 48h;

With hydrogen; nickel; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1002/ejoc.201301566

Reference yield: 98.0%

2‐azido‐1‐isopropyl‐4‐methylcyclohexane (898543-45-8,898543-46-9) → rac-menthylamine (2216-54-8,4894-99-9,7231-40-5,16934-77-3,20706-69-8,20706-70-1,21411-81-4,23399-21-5,51743-63-6,66609-74-3,85549-06-0,787534-09-2)

Guidance literature:

With hydrogen; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1055/s-0030-1258295

Reference yield: 88.0%

menthol (89-78-1) → 2-isopropyl-5-methyl-cyclohexylamine (21411-81-4,787534-09-2)

Guidance literature:

With sodium azide; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; at 90 ℃; for 7h;

DOI:10.1080/00397910008087402

upstream raw materials:

L-Tartaric acid

rac-menthylamine

(2R,5S)-menthone

ammonium formate

Downstream raw materials:

N-menthyl-butyramide

N-menthyl-formamide

N-menthyl-acetamide

benzylidene-menthyl-amine

Refernces

REDUCTIVE AMINATION OF l-MENTHOL BY ALIPHATIC NITRILES

10.1007/BF00568510

The research investigates the reductive amination of l-menthol using aliphatic nitriles, aiming to understand the stereochemical composition of the products and propose a mechanism for the reaction. The study utilized a copper-alumina catalyst modified with lithium hydroxide and conducted the reaction under specific conditions of temperature, pressure, and space velocity. The chemicals involved included l-menthol, aliphatic nitriles such as acetonitrile, acrylonitrile, and butyronitrile, and a catalyst composed of 15% copper and 6% lithium hydroxide on alumina. The results showed that the reaction produced a mixture of isomeric optically active N-alkyl derivatives of menthylamine, neomenthylamine, isomenthylamine, and neoisomenthylamine in a ratio of 54:24:17:5.