34737-70-7

Basic information

• Product Name: 1,2-Ethanediol, 1,2-bis(2-methylphenyl)-, (1R,2S)-rel-
• Synonyms: meso-1,2-di(o-methylphenyl)ethane-1,2-diol;2,2'-Dimethyl-hydrobenzoin od. 1,2-Bis-(2-methyl-phenyl)-ethan-1,2-diol
• CAS NO: 34737-70-7
• Molecular Formula: C16H18O2
• Molecular Weight: 242.318
• Mol File: 34737-70-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 111 - 116 °C
• Boiling Point: 406.6±40.0 °C(Predicted)
• Density: 1.142±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2-Ethanediol, 1,2-bis(2-methylphenyl)-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol, 1,2-bis(2-methylphenyl)-, (1R,2S)-rel-(34737-70-7)
• EPA Substance Registry System: 1,2-Ethanediol, 1,2-bis(2-methylphenyl)-, (1R,2S)-rel-(34737-70-7)

Safety Data

• Hazardous Substances Data: 34737-70-7(Hazardous Substances Data)

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 4389-39-3 2-hydroxy-1,2-bis(2-methylphenyl)ethanone 
• 36888-18-3 (E)-2,2'-dimethylstilbene 
• 89-95-2 2-methyl-benzyl alcohol 
• 1530-36-5 [(2-methylphenyl)methyl]triphenylphosphonium bromide 
• 603-35-0 triphenylphosphine 
• 89-92-9 2-methylbenzyl bromide 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 74-88-4 methyl iodide 
• 5294-03-1 di-o-tolylethyne 

Downstream Products

• 916525-60-5 1,2-bis(2-methylphenyl)-2-[(7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan-2-yl)oxy]ethanol 
• 916525-72-9 (1R,2S)-1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethanol 
• 916525-82-1 hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethyl ester 
• 916525-77-4 oxophenylacetic acid (1R,2S)-1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethyl ester 
• 916525-65-0 [1,2-bis(2-methylphenyl)-2-(2-methylpropoxy)ethoxy]-7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan 

Relevant articles and documents

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

Oxidative and Redox-Neutral Approaches to Symmetrical Diamines and Diols by Single Electron Transfer/Hydrogen Atom Transfer Synergistic Catalysis

Homocoupling reactions of benzylamines and benzyl alcohols were examined under synergistic catalysis conditions with a photoredox catalyst and thiobenzoic acid as a hydrogen atom abstractor. When pivalaldehyde was used as an electron acceptor, oxidative dimerization proceeded selectively, whereas the use of benzaldehydes or iminium ions as electron acceptors resulted in redox-neutral coupling. These reactions afforded symmetrical 1,2-diamines and 1,2-diols in good yields.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).