6957-08-0

Basic information

• Product Name: 1-(m-Tolyl)cyclohexanol
• Synonyms: 1-(m-Tolyl)cyclohexanol
• CAS NO: 6957-08-0
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28
• Mol File: 6957-08-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 309.3°C at 760 mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 1.043g/cm³
• Vapor Pressure: 0.000279mmHg at 25°C
• Refractive Index: 1.554
• PKA: 14.77±0.20(Predicted)
• CAS DataBase Reference: 1-(m-Tolyl)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(m-Tolyl)cyclohexanol(6957-08-0)
• EPA Substance Registry System: 1-(m-Tolyl)cyclohexanol(6957-08-0)

Safety Data

• Hazardous Substances Data: 6957-08-0(Hazardous Substances Data)

Usage

General Description

1-(m-Tolyl)cyclohexanol is a chemical compound with the molecular formula C13H18O. It is a cyclohexanol derivative with a methyl group attached to the meta position of the phenyl ring. 1-(m-Tolyl)cyclohexanol is commonly used in the production of fragrances, pharmaceuticals, and as a precursor in organic synthesis. It is a colorless to pale yellow liquid with a mild, floral odor. It is also known for its potential for skin irritation and eye damage, and should be handled with care. Its main applications include its use as a fragrance ingredient in personal care products and as a reactant in the synthesis of various organic compounds.

InChI:InChI=1/C13H18O/c1-11-6-5-7-12(10-11)13(14)8-3-2-4-9-13/h5-7,10,14H,2-4,8-9H2,1H3

Upstream product

• 625-95-6 3-Iodotoluene 
• 108-94-1 cyclohexanone 
• 17933-03-8 m-tolylboronic acid 
• 223799-24-4 2-(3-methyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 
• 108-93-0 cyclohexanol 
• 591-17-3 meta-bromotoluene 
• 28987-79-3 m-tolylmagnesium bromide 
• 79421-98-0 2,4,6-tris(m-tolyl)boroxine 

Downstream Products

• 2201-28-7 1-<3-Methyl-phenyl>-cyclohexylamin 
• 4575-46-6 1-cyclohexyl-3-methylbenzene 
• 643-93-6 3-methylbiphenyl 
• 22618-50-4 3'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 

Relevant articles and documents

Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization

The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Bronsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.

Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.

Synthesis and Anticonvulsant Activity of 1-Phenylcyclohexylamine Analogues

Thirty-eight analogues of 1-phenylcyclohexylamine (PCA), a phencyclidine (PCP) derivative, were examined for their activities in the mouse maximal electroshock (MES) seizure test and in a motor-toxicity assay.In addition, we determined the binding affinities of the compounds for PCP acceptor sites in rat brain membranes labeled with -1-piperidine.Many of the analogues were protective against MES seizures (ED50s of 4-41 mg/kg, ip) and all of these compounds caused motor toxicity.The potencies in the motor toxicity and MES seizure tests showed a moderate correlation with the affinities for PCP sites.Several analogues exhibited a greater separation of potencies in the motor toxicity and MES seizure tests than did the parent compound PCA.These were obtained by (i) 3-methylation of the cyclohexyl ring trans to the phenyl ring, (ii) methoxylation at the ortho position on the phenyl ring, and (iii) contraction of the cyclohexane ring to form the corresponding cyclopentane.