5623-26-7

Basic information

• Product Name: ALPHA-HYDROXY-ALPHA-METHYLBENZYL PHENYL KETONE
• Synonyms: RARECHEM AQ A2 0041;2-HYDROXY-1,2-DIPHENYL-1-PROPANONE;ALPHA-HYDROXY-ALPHA-METHYLBENZYL PHENYL KETONE;LABOTEST-BB LT00848218;alpha-Methylbenzoin;à-hydroxy-à-methylbenzyl phenyl ketone;à-methylbenzoin;ɑ-Hydroxy-ɑ-methylbenzyl phenyl ketone, 98%
• CAS NO: 5623-26-7
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• Mol File: 5623-26-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 66-67°C
• Boiling Point: 373.1°Cat760mmHg
• Flash Point: 159.3°C
• Appearance: /
• Density: 1.151g/cm³
• Vapor Pressure: 3.15E-06mmHg at 25°C
• Refractive Index: 1.592
• BRN: 2049961
• CAS DataBase Reference: ALPHA-HYDROXY-ALPHA-METHYLBENZYL PHENYL KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-HYDROXY-ALPHA-METHYLBENZYL PHENYL KETONE(5623-26-7)
• EPA Substance Registry System: ALPHA-HYDROXY-ALPHA-METHYLBENZYL PHENYL KETONE(5623-26-7)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 5623-26-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 984, 1955 DOI: 10.1021/ja01609a053The Journal of Organic Chemistry, 53, p. 2381, 1988Tetrahedron Letters, 33, p. 2621, 1992 DOI: 10.1016/S0040-4039(00)79041-1

InChI:InChI=1/C15H14O2/c1-15(17,13-10-6-3-7-11-13)14(16)12-8-4-2-5-9-12/h2-11,17H,1H3

Upstream product

• 75-16-1 methylmagnesium bromide 
• 134-81-6 benzil 
• 67-56-1 methanol 
• 98-86-2 acetophenone 
• 100-47-0 benzonitrile 
• 917-54-4 methyllithium 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 74-88-4 methyl iodide 
• 451-40-1 phenyl benzyl ketone 
• 1528-00-3 di-n-butyldimethylstannane 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 98-88-4 benzoyl chloride 
• 80-48-8 methyl p-toluene sulfonate 
• 4344-45-0 5,6-Diphenyl-2,3-dihydro-[1,4]dioxine 

Downstream Products

• 4452-11-3 1,2-diphenylprop-2-en-1-one 
• 92435-53-5 3-chloro-1,2-diphenylpropan-1-one 
• 115963-83-2 2-hydroxy-1,2,5,6-tetraphenyl-hexane-1,6-dione 
• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 4915-86-0 2-acetoxy-1,2-diphenyl-propan-1-one 
• 129263-06-5 (S)-2-hydroxy-1,2-diphenylpropan-1-one 
• 129263-07-6 (+)-(R)-2-hydroxy-1,2-diphenylpropan-1-one 
• 1037383-83-7 (rac)-1-methyl-2-oxo-1,2-diphenylethyl 2-[N-((1,1-dimethylethoxy)carbonyl)amino]ethanoate 
• 41848-64-0 3-bromo-1,2-diphenylpropan-1-one 
• 859317-00-3 1-(4-methoxy-phenyl)-2,3,5-triphenyl-cyclopentane-1,2-diol 
• 855365-41-2 1-(4-methoxy-phenyl)-2,4,5-triphenyl-pentane-1,5-dione 
• 854917-01-4 1-(4-chloro-phenyl)-2,3,5-triphenyl-cyclopentane-1,2-diol 

Relevant articles and documents

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

The cross-selective titanium(III)-catalysed acyloin reaction

A titanium(iii)-catalysed intermolecular reductive coupling of ketones or imines with nitriles is described, which gives direct access to α-hydroxylated and α-aminated ketones. This coupling reaction is cross-selective and a catalytic version of the classical acyloin condensation. A reaction mechanism that is supported by first DFT calculations is discussed. the Partner Organisations 2014.

A dinuclear palladium catalyst for α-Hydroxylation of carbonyls with O2

A chemo- and regioselective α-hydroxylation reaction of carbonyl compounds with molecular oxygen as oxidant is reported. The hydroxylation reaction is catalyzed by a dinuclear Pd(II) complex, which functions as an oxygen transfer catalyst, reminiscent of an oxygenase. The development of this oxidation reaction was inspired by discovery and mechanism evaluation of previously unknown Pd(III)-Pd(III) complexes.