5472-13-9

Basic information

• Product Name: 2-Methylbenzhydrol
• Synonyms: PHENYL O-TOLYL CARBINOL;PHENYL-O-TOLYL-METHANOL;TIMTEC-BB SBB005873;(2-METHYLPHENYL)-PHENYLCARBINOL;2-METHYLDIPHENYLMETHANOL;2-METHYLBENZHYDROL;AURORA KA-7055;2-Methyldiphenylmethanol~Phenyl o-tolyl carbinol
• CAS NO: 5472-13-9
• Molecular Formula: C₁₄H₁₄O
• Molecular Weight: 198.26
• EINECS: 226-810-6
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 5472-13-9.mol
• Article Data: 150

Chemical Properties

• Melting Point: 93-95 °C(lit.)
• Boiling Point: 323 °C(lit.)
• Flash Point: 323°C
• Appearance: almost white adhering powder
• Density: 1.0074 (rough estimate)
• Vapor Pressure: 0.000111mmHg at 25°C
• Refractive Index: 1.5381 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly),
• PKA: 13.56±0.20(Predicted)
• BRN: 1952703
• CAS DataBase Reference: 2-Methylbenzhydrol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzhydrol(5472-13-9)
• EPA Substance Registry System: 2-Methylbenzhydrol(5472-13-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5472-13-9(Hazardous Substances Data)

Usage

Description

2-Methylbenzhydrol is an organic compound derived from benzhydrol, featuring a methyl group substitution at the 2nd position. It is an almost white adhering powder and serves as a metabolite of the antihistaminic Orphenadrine (O695300). Its chemical structure allows for various chemical reactions, such as etherification with tropine and reduction in specific conditions, making it a versatile compound in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
2-Methylbenzhydrol is used as an intermediate in the synthesis of various pharmaceutical compounds due to its ability to undergo etherification and reduction reactions. Its role in the production of tropinyl 2-methyl-benzhydryl ether hydrobromide (BS 6825) highlights its importance in the development of antihistaminic medications.
Used in Chemical Industry:
In the chemical industry, 2-Methylbenzhydrol is utilized as a starting material for the creation of diphenylmethane derivatives. Its reduction in acetic acid containing iodine and aqueous hypophosphorous acid yields diphenylmethanes, which are valuable in the synthesis of various organic compounds and materials.

Synthesis Reference(s)

Synthetic Communications, 5, p. 441, 1975 DOI: 10.1080/00397917508065578

InChI:InChI=1/C14H14O/c1-11-7-5-6-10-13(11)14(15)12-8-3-2-4-9-12/h2-10,14-15H,1H3

Upstream product

• 20002-32-8 2,2'-dimethylbenzopinacol 
• 131-58-8 2-Methylbenzophenone 
• 932-31-0 ortho-tolylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 103-73-1 Phenetole 
• 693-03-8 n-butyl magnesium bromide 
• 109-72-8 n-butyllithium 
• 52669-93-9 hex-5-enylmagnesium chloride 
• 1586-01-2 (2-hydroxymethylphenyl)phenylmethanol 
• 108-86-1 bromobenzene 
• 529-20-4 2-methylphenyl aldehyde 
• 22776-23-4 α-o-tolylbenzyl cation 
• 100-58-3 phenylmagnesium bromide 
• 60-29-7 diethyl ether 

Downstream Products

• 41870-52-4 α-phenyl-o-methylbenzyl chloride 
• 713-36-0 2-benzyltoluene 
• 2212-36-4 N,N,N'-Trimethyl-N'-[2-(phenyl-o-tolyl-methoxy)-ethyl]-ethane-1,2-diamine 
• 37834-56-3 4'-Hydroxy-2-methyl-triphenylmethan 
• 92189-38-3 2-methyl-benzhydryl bromide 
• 37834-54-1 1,2-diphenyl-1,2-di-o-tolyl-ethane 
• 17322-49-5 N,N-Dimethyl-2-<(o-methyl-α-phenylbenzyl)oxy>acetamid 
• 145701-78-6 2-(Phenyl-o-tolyl-methylsulfanyl)-ethylamine; hydrochloride 
• 131-58-8 2-Methylbenzophenone 
• 55190-63-1 1-[methoxy(phenyl)methyl]-2-methylbenzene 
• 20263-93-8 -essigsaeure 
• 22776-23-4 α-o-tolylbenzyl cation 
• 22135-59-7 <2-Chlor-aethyl>-<2-methyl-benzhydryl>-aether 
• 18552-76-6 2-(Phenyl-o-tolyl-methoxy)-acetamide 

Relevant articles and documents

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Manganese catalyzed asymmetric transfer hydrogenation of ketones

The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.

Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand

We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.