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

Description

meso-1,2-Diphenyl-1,2-ethanediol is a white crystalline powder with unique chemical properties that make it suitable for various applications across different industries.

Uses

Used in Chemical Synthesis:
meso-1,2-Diphenyl-1,2-ethanediol is used as a key intermediate for the preparation of trans-methyl meso-hydrobenzoin phosphite, which is an important compound in the chemical industry.
Used in Pharmaceutical Industry:
meso-1,2-Diphenyl-1,2-ethanediol is used as a chiral catalyst for the desymmetrization of meso-hydrobenzoin, a process that is crucial in the synthesis of various pharmaceutical compounds.
Used in Chemical Reactions:
meso-1,2-Diphenyl-1,2-ethanediol is used as a reactant in the conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide, which is a significant reaction in organic chemistry.

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

• 19456-17-8 (4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one 
• 693-03-8 n-butyl magnesium bromide 
• 100-52-7 benzaldehyde 
• 556-56-9 allyl iodid 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 645-49-8 cis-stilben 
• 134-81-6 benzil 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 119-53-9 2-hydroxy-2-phenylacetophenone 

Downstream Products

• 6067-45-4 4,4'-dinitrobenzil 
• 27797-53-1 4,5-diphenyl-[1,3]-dioxolan-2-one 
• 40058-69-3 2,3-dimethyl-7,8-diphenyl-1,4,6,9-tetraoxa-5λ⁵-phospha-spiro[4.4]nonane 
• 104833-17-2 (4S,5R)-2,2,2,4,5-Pentaphenyl-2λ⁵-[1,3,2]dioxaphospholane 
• 87248-50-8 <2R,2'R-(2α,2'α,3aα,3a'α,4α,4'α,7α,7'α,7aα,7a'α)>-2,2'-Oxybis(2,3,3a,4,5,6,7,7a-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran) 
• 100680-93-1 <2R-<2α(αR^*,βS^*),3aα,4α,7α,7aα>>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-α-phenylbenzolethanol 
• 100680-94-2 <2R-<2α(αS^*,βR^*),3aα,4α,7α,7aα>>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-α-phenylbenzolethanol 
• 87218-36-8 <2R-(2α(S^*,S^*),3aα,4α,7α,7aα)>-2-(7,8,8-Trimethyl-octahydro-4,7-methano-1-benzofuran-2-yloxy)-1,2-diphenylethanol 
• 87218-36-8 (R)-1,2-Diphenyl-2-((1R,2S,4R,6S,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethanol 
• 85891-96-9 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1R,2R)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-1,2-diphenyl-ethyl ester 
• 85891-96-9 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1S,2S)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-1,2-diphenyl-ethyl ester 
• 29509-31-7 2-Phenoxy-1,2-diphenylethan-1-ol 
• 4456-34-2 bis(4-methoxyphenyl)telluride 
• 100-52-7 benzaldehyde 

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.

Efficient splitting of alcohols into hydrogen and C–C coupled products over ultrathin Ni-doped ZnIn2S4 nanosheet photocatalyst

Integrating selective organic synthesis with hydrogen (H2) evolution in one photocatalytic redox reaction system sheds light on the underlying approach for concurrent employment of photogenerated electrons and holes towards efficient production of solar fuels and chemicals. In this work, a facile one-pot oil bath method has been proposed to fabricate a noble metal-free ultrathin Ni-doped ZnIn2S4 (ZIS/Ni) composite nanosheet for effective solar-driven selective dehydrocoupling of benzyl alcohol into value-added C–C coupled hydrobenzoin and H2 fuel, which exhibits higher performance than pure ZIS nanosheet. The remarkably improved photoredox activity of ZIS/Ni is mainly attributed to the optimized electron structure featuring narrower band gap and suitable energy band position, which facilitates the ability of light harvesting and photoexcited charge carrier separation and transfer. Furthermore, it has been demonstrated that it is feasible to employ ZIS/Ni for various aromatic alcohols dehydrocoupling to the corresponding C–C coupled products. It is expected that this work can stimulate further interest on the establishment of innovative photocatalytic redox platform coupling clean solar fuels synthesis and selective organic conversion in a sustainable manner.

Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties

A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.