579-43-1

Basic information

• Product Name: meso-1,2-Diphenyl-1,2-ethanediol
• Synonyms: 1,2-Ethanediol, 1,2-diphenyl-, (R*,S*)-;1,2-Ethanediol, 1,2-diphenyl-, meso-;meso-Stilbene glycol;1,2-DIPHENYL-1,2-ETHANEDIOL;MESO-1,2-DIPHENYLETHYLENE GLYCOL;MESO-1,2-DIPHENYL-1,2-ETHANEDIOL;MESO-HYDROBENZOIN;HYDROBENZOIN MESO
• CAS NO: 579-43-1
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• EINECS: 207-758-3
• Mol File: 579-43-1.mol
• Article Data: 488

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 373 °C at 760 mmHg
• Flash Point: 179.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.193 g/cm³
• Vapor Pressure: 3.18E-06mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• Solubility: Soluble in hot alcohol or chloroform.
• PKA: 13.38±0.20(Predicted)
• Merck: 14,4777
• BRN: 2050814
• CAS DataBase Reference: meso-1,2-Diphenyl-1,2-ethanediol(CAS DataBase Reference)
• NIST Chemistry Reference: meso-1,2-Diphenyl-1,2-ethanediol(579-43-1)
• EPA Substance Registry System: meso-1,2-Diphenyl-1,2-ethanediol(579-43-1)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 579-43-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

meso- Hydrobenzoin has been used in the preparation of trans-methyl meso- hydrobenzoin phosphite.

General Description

Desymmetrization of meso-hydrobenzoin using chiral phosphine catalyst has been reported. Conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide has been reported.

Purification Methods

meso-Hydrobenzoin [579-43-1] M 214.3, m 139o, 139-140o. Crystallise it from EtOH or water. [Beilstein 6 H 1003, 6 I 490, 6 II 967. 6 III 5429, 6 IV 6682.]

InChI:InChI=1/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14+

Upstream product

• 79-21-0 peracetic acid 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 555-75-9 aluminum ethoxide 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 91-17-8 decalin 
• 60-29-7 diethyl ether 
• 677-22-5 tert-butylmagnesium chloride 
• 71-43-2 benzene 
• 28276-08-6 1,1-dimethylpropylmagnesium chloride 
• 108-88-3 toluene 
• 100-52-7 benzaldehyde 
• 74-95-3 1,1-dibromomethane 
• 64-17-5 ethanol 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 947-91-1 Diphenylacetaldehyde 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 
• 13440-24-9 1,2-dibromo-1,2-diphenylethane 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 38270-63-2 2-benzhydryl-4,5-diphenyl-[1,3]dioxolane 
• 100-52-7 benzaldehyde 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 6067-45-4 4,4'-dinitrobenzil 
• 27797-53-1 4,5-diphenyl-[1,3]-dioxolan-2-one 
• 19455-94-8 (meso-bibenzyldiyl-(α.α'))-sulfite 
• 15951-99-2 meso-1,2-dichloro-1,2-diphenylethane 
• 97176-53-9 2-hydroxy-2-oxo-4,5-diphenyl-1,3,2-dioxaphospholane 

Relevant articles and documents

Diastereoselective Ce(III)-catalyzed pinacol couplings of aldehydes

Aliphatic and aromatic aldehydes were converted into the corresponding pinacoles by using different cerium catalysts. Ce(OtBu)3 proved to be superior over other cerium(III) catalysts. Especially the highly diastereoselective pinacol coupling of sterically non demanding aldehydes such as hexanal is remarkable.

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

A convenient pinacol coupling of diaryl ketones with B2pin2viapyridine catalysis

A convenient, pyridine-boryl radical-mediated pinacol coupling of diaryl ketones is developed. In contrast to the conventional pinacol coupling that requires sensitive reducing metal, the current method employs a stable diboron reagent and pyridine Lewis base catalyst for the generation of a ketyl radical. The newly developed process is operationally simple, and the desired diols are produced with excellent efficiency in up to 99% yield within 1 hour. The superior reactivity of diaryl ketone was observed over monoaryl carbonyl compounds and analyzed by DFT calculations, which suggests the necessity of both aromatic rings for the maximum stabilization of the transition states.