71776-58-4

Basic information

• Product Name: 1,2-Ethanediol, 1,2-bis(2-chlorophenyl)-, (1R,2S)-rel-
• CAS NO: 71776-58-4
• Molecular Formula: C14H12Cl2O2
• Molecular Weight: 283.154
• Mol File: 71776-58-4.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediol, 1,2-bis(2-chlorophenyl)-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol, 1,2-bis(2-chlorophenyl)-, (1R,2S)-rel-(71776-58-4)
• EPA Substance Registry System: 1,2-Ethanediol, 1,2-bis(2-chlorophenyl)-, (1R,2S)-rel-(71776-58-4)

Safety Data

• Hazardous Substances Data: 71776-58-4(Hazardous Substances Data)

Upstream product

• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 95-49-8 2-methylchlorobenzene 
• 10577-21-6 1,2-Bis(2-chlorophenyl)-1-chloroethane 
• 89-98-5 2-chloro-benzaldehyde 
• 25144-38-1 (E)-2,2'-dichlorostilbene 
• 35190-16-0 2,2'-dichlorobenzoin 
• 21854-95-5 2,2'-dichlorobenzil 

Downstream Products

• 668991-40-0 (S)-1,2-bis-(2-chloro-phenyl)-2-hydroxy-ethanone 
• 249626-07-1 (R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one 
• 929219-24-9 4,5-bis(2-chlorophenyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-dioxolane 
• 84574-53-8 (2S,3S,5R,6R)-2,3,5,6-Tetrakis-(2-chloro-phenyl)-[1,4]dioxane 
• 84574-54-9 (2S,3R,5S,6R)-2,3,5,6-Tetrakis-(2-chloro-phenyl)-[1,4]dioxane 

Relevant articles and documents

Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst

The carbon-carbon bond cleavage of 1,2-diols is an important chemical transformation. Although traditional stoichiometric and catalytic oxidation methods have been widely used for this transformation, an efficient and valuable method should be further explored from the views of reusable catalysts, less waste, and convenient procedures. Herein an inorganic-ligand supported iron catalyst (NH4)3[FeMo6O18(OH)6]·7H2O was described as a heterogeneous molecular catalyst in acetic acid for this transformation in which hydrogen peroxide was used as the terminal oxidant. Under the optimized reaction conditions, carbon-carbon bond cleavage of 1,2-diols could be achieved in almost all cases and carboxylic acids or ketones could be afforded with a high conversion rate and high selectivity. Furthermore, the catalytic system was used efficiently to degrade renewable biomass oleic acid. Mechanistic insights based on the observation of the possible intermediates and control experiments are presented.

Chiral Benzoins via Asymmetric Transfer Hemihydrogenation of Benzils: The Detail that Matters

The synthesis of enantiomerically pure benzoins by hydrogenation of readily available benzils has been long thwarted by their base-sensitivity. We show here that an iron(II) hydride complex catalyzes the asymmetric transfer hydrogenation of benzils from 2-propanol. When strictly base-free conditions are granted, excellent enantioselectivity is achieved even with o-substituted substrates, which are particularly challenging to prepare with other methods. Hence, under optimized reaction conditions, chiral benzoins were prepared in good yields (up to 83%) and excellent enantioselectivity (up to 98% ee) in short reaction times (30-75 min). Also, this work confirms that both enantiomers of the benzoin products can be accessed when a metal catalyst is used, which is a clear advantage over enzymatic methods.

MeOH or H2O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds

A variety of carbonyl compounds were treated by allylSmBr (allylSmBr) with MeOH as the cosolvent to have further insights on the previously reported reductive coupling of aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted by allylSmBr.