19043-03-9

Basic information

• Product Name: (1R,2R)-(-)-trans-2-methylcyclohexanol
• Synonyms: (1R,2R)-(-)-trans-2-methylcyclohexanol
• CAS NO: 19043-03-9
• Molecular Weight: 114.188
• Mol File: 19043-03-9.mol
• Article Data: 39

Chemical Properties

• Melting Point: -4.3--3.7 °C
• Boiling Point: 66.7 °C(Press: 12 Torr)
• Density: 0.9247 g/cm3
• CAS DataBase Reference: (1R,2R)-(-)-trans-2-methylcyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(-)-trans-2-methylcyclohexanol(19043-03-9)
• EPA Substance Registry System: (1R,2R)-(-)-trans-2-methylcyclohexanol(19043-03-9)

Safety Data

• Hazardous Substances Data: 19043-03-9(Hazardous Substances Data)

Usage

Description

(1R,2R)-(-)-trans-2-methylcyclohexanol, also known as trans-menthol, is a chemical compound characterized by its minty, camphor-like odor and a cooling sensation when applied to the skin. It is widely recognized for its stereochemistry, which is crucial in many organic synthesis reactions, particularly for the preparation of chiral compounds.

Uses

Used in Perfumery and Flavoring Industry:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a fragrance ingredient and flavoring agent for its distinct minty and cooling properties, enhancing the sensory experience of various consumer products.
Used in Pharmaceutical Industry:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a local anesthetic and as a component in over-the-counter medications for coughs and colds, leveraging its cooling effect and soothing properties to alleviate symptoms.
Used in Organic Synthesis:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as a key intermediate in the synthesis of chiral compounds, playing a significant role in the production of enantiomerically pure substances for pharmaceutical and chemical applications.
Used in Pest Control Products:
(1R,2R)-(-)-trans-2-methylcyclohexanol is used as an insecticide in pest control products, capitalizing on its natural insecticidal properties to manage and control pests effectively.

Upstream product

• 591-49-1 1-methylcyclohex-1-ene 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 583-59-5 2-Methylcyclohexanol 
• 583-60-8 2-Methylcyclohexanone 
• 148615-29-6 (1R,2R)-trans-2-methylcyclohexyl octanoate 
• 5726-19-2 2-methylcyclohexyl acetate 
• 7443-52-9 (+/-)-trans-2-methylcyclohexanol 
• 5726-24-9 Heptanoic acid (R)-2-methyl-cyclohexyl ester 
• 22554-27-4 (S)-2-methylcyclohexanone 
• 82166-21-0 methyl cyclohexane 
• 1373216-32-0 tris(4-isopropylphenyl)silyl chloride 
• 7443-70-1 cis-2-methylcyclohexanol 
• 99299-20-4 (2R,4R)-2,4,7-trimethyl-1,5-dioxaspiro[5.5]undecane 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Downstream Products

• 2133-66-6 2-(trans-2-methylcyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 931-11-3 (1R,2R)-2-methyl-1-cyclohexylamine 
• 111-71-7 heptanal 
• 591-49-1 1-methylcyclohex-1-ene 
• 5726-20-5 trans-2-Methyl-cyclohexyl-propionat 
• 836-05-5 N-[(1R, 2R)-2-methylcyclohexyl]benzamide 
• 1350552-16-7 carbonic acid 1-chloroethyl ester (1R,2R)-2-methylcyclohexyl ester 
• 146566-58-7 (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1R,2R)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester 

Relevant articles and documents

A crystalline, internally-coordinated chloroborane for asymmetric hydroboration

Asymmetric hydroboration is an important method in the preparation of enantiomerically-enriched compounds that are necessary in many areas of chemistry. Here is reported the preparation of a unique chiral chloroborane-internal ether complex and its applic

Catalytic carbonyl hydrosilylations: Via a titanocene borohydride-PMHS reagent system

Reduction of a wide range of aldehydes and ketones with catalytic amounts of titanocene borohydride in concert with a stoichiometric poly(methylhydrosiloxane) (PMHS) reductant is reported. Preliminary mechanistic studies demonstrate that the reaction is mediated by a reactive titanocene(iii) complex, whose oxidation state remains constant throughout the reaction.

P-Tolylimido rhenium(v) complexes with phenolate-based ligands: Synthesis, X-ray studies and catalytic activity in oxidation with tert-butylhydroperoxide

The reactions of mer-[Re(p-NTol)X3(PPh3)2] (X = Cl, Br) with chelating phenolate-based ligands (2-(2-hydroxy-5-methylphenyl)benzotriazole (HL1), 2-(2-hydroxyphenyl)benzothiazole (HL2) or 2-(2-hydroxyphenyl)benzoxazole (HL3)) afforded a series of p-tolylimido rhenium(v) complexes cis- or trans-(X,X)-[Re(p-NTol)X2(L)(PPh3)]·yMeCN (where X = Cl, Br; L = L1, L2, L3 and y = 0-2) and [Re(p-NTol)X(L)(PPh3)2]Z·pPPh3 (where X = Cl, Br; Z = ReO4, PF6; L = L1, L2, L3 and p = 0 or 1). The reported compounds were characterized by elemental analysis, FT-IR, NMR (1H, 13C and 31P) and X-ray crystallography. Interestingly, the halide ions of [Re(p-NTol)Cl2(L1)(PPh3)]·MeCN (1) and [Re(p-NTol)Cl2(L2)(PPh3)]·2MeCN (3) are in cis relative dispositions, whereas the complexes [Re(p-NTol)Br2(L)(PPh3)] (L1 for 2, L2 for 4 and L3 for 6) and [Re(p-NTol)Cl2(L3)(PPh3)] (5) were found to be trans-(X,X) isomers. The compounds [Re(p-NTol)X(L)(PPh3)2](PF6) (X = Cl, Br; L = L1 and L2) and [Re(p-NTol)X(L3)(PPh3)2](PF6)·PPh3 (X = Cl, Br) have been tested in oxidative catalysis. A few compounds exhibited very good catalytic properties in oxidation of alcohols with tert-BuOOH (TBHP) in acetonitrile solution at moderate temperatures. Complex [Re(p-NTol)Cl(L2)(PPh3)2]PF6 (13) is the catalyst of choice for oxidation of 1-phenylethanol to acetophenone (in 80% yield; turnover number attained 290 after 30 h) and cyclooctanol to cyclooctanone (in 88% yield). Notably lower activity has been found in the oxidation of alkanes with TBHP. Product distribution in the oxidation of methylcyclohexane indicates some steric hindrance around the reaction center.