21651-83-2

Basic information

• Product Name: (1R,2R)-2-(MethylaMino)cyclohexanol
• Synonyms: (1R,2R)-2-(MethylaMino)cyclohexanol;(1R-trans)-2-(Methylamino)-cyclohexanol;(1R,2R)-(-)-2-(Methylamino)cyclohexanol (1R-trans)-2-(Methylamino)-cyclohexanol;(1R,2R)-2-(Methylamino)cyclohexanol,99%e.e.
• CAS NO: 21651-83-2
• Molecular Formula: C₇H₁₅NO
• Molecular Weight: 129.2001
• Mol File: 21651-83-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (1R,2R)-2-(MethylaMino)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-(MethylaMino)cyclohexanol(21651-83-2)
• EPA Substance Registry System: (1R,2R)-2-(MethylaMino)cyclohexanol(21651-83-2)

Safety Data

• Hazardous Substances Data: 21651-83-2(Hazardous Substances Data)

Usage

General Description

(1R,2R)-2-(MethylaMino)cyclohexanol, also known as menthoxypropanediol, is a chiral compound that consists of a cyclohexane ring with a hydroxyl group and an amino group as substituents. It is used as an active ingredient in cosmetic and personal care products for its cooling and soothing properties, making it a popular additive in products such as skin creams, lotions, and lip balms. (1R,2R)-2-(MethylaMino)cyclohexanol is often used to provide a refreshing sensation on the skin and has also been studied for its potential as a treatment for certain skin conditions such as itching and inflammation, due to its ability to activate specific receptors in the skin.

Upstream product

• 6628-80-4 trans-2-chlorocyclohexanol 
• 20431-81-6 rac-trans-2-methylamino-cyclohexanol 
• 853953-23-8 (1R,2R)-2-methylamino-cyclohexanol (R)-mandelic acid salt 
• 286-20-4 cyclohexane-1,2-epoxide 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 
• 24796-87-0 2-bromo-cyclohexanol 
• 74-89-5 methylamine 
• 38898-70-3 cis-2-amino-cyclohexanol-⁽¹⁾ 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 83196-12-7 [((1R,2R)-2-Hydroxy-cyclohexyl)-methyl-amino]-acetonitrile 
• 83196-13-8 [Methyl-((R)-2-oxo-cyclohexyl)-amino]-acetonitrile 
• 83196-15-0 cis-3a-phenyl-4-oxo-decahydrocycloheptapyrrole 
• 83196-14-9 {[(1R,2R)-2-Hydroxy-2-(1-phenyl-vinyl)-cyclohexyl]-methyl-amino}-acetonitrile 
• 90227-79-5 cis-(2-Hydroxy-cyclohexyl)-methyl-aminomethan-sulfonsaeure 
• 116203-82-8 N-nitrosomethyl-N-2-oxocyclohexylamine 
• 882409-15-6 (1R,2S)-cis-2-(N-methyl)amino-1-cyclohexanol 
• 112708-89-1 (1S,2R)-cis-2-(N-methyl)amino-1-cyclohexanol 

Relevant articles and documents

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.

The use of benzamide derivatives of secondary amines for stereochemical studies by circular dichroism

The benzamide chromophore is widely used as a Cottonogenic derivative of primary amines for stereochemical studies by circular dichroism. The assignments based on the exciton chirality method are reliable since the benzamide group has well-defined geometry and conformation. A recent report U.D. Chisholm, J. Golik, B. Krishnan, J.A. Matson, D.L. Van Vranken, J. Am. Chem. Soc. 1999, 121: 3801-3802) claimed a caveat in the application of the exciton chirality method to benzamides derived from secondary amines. By the use of benzoyl derivatives of amino alcohols (1-4) and diamines (5, 6) of known absolute configuration we demonstrate that the 250-210 nm range exciton Cotton effects due to secondary and tertiary benzamides are generally of opposite sign. The origin of such disparity is traced to different conformational equilibria of the amide C-N bond in secondary and tertiary benzamides, as shown by semiempirical molecular modelling and NMR data. This feature can be useful in the determination of absolute configuration by analysis of the CD spectra due to exciton coupling of tertiary benzamides.

O.N-Bis(diphenylphosphino) Derivatives of Chiral trans- and cis-2-Aminocyclohexanols: Synthesis and Enantioselective Behaviour as Ligands in Rh-based Homogeneous Hydrogenation Catalysts

trans- and cis-2-Methylamino cyclohexanols (MAC) were prepared in enantiomerically pure forms and transformed into O.N-bis(diphenylphosphino) derivatives ("PONP").An analogous trans-1R;2R-aminocyclohexanol PONP could only be isolated in an impure form, whereas the attempted synthesis of PONP's of diastereomeric trans-2-(N-α-phenylethylamino)-cyclohexanols failed.Cationic Rh(I)-chelates of the new PONP's catalyzed the enantioselective hydrogenation of dehydro-α-acylamino acids with /= 97percent ee.A comparison of the enantiodiscriminating properties of the MAC-PONP's with structurally related chiral ligands leads to surprising conclusions.