37580-81-7

Basic information

• Product Name: 1,2-Ethanediol,1,2-bis(4-chlorophenyl)-, (1R,2S)-rel-
• Synonyms: 1,2-Ethanediol,1,2-bis(4-chlorophenyl)-, (R*,S*)-; (1R,2S)-rel-1,2-bis(4-chlorophenyl)-1,2-ethanediol;meso-4,4'-Dichlorohydrobenzoin
• CAS NO: 37580-81-7
• Molecular Formula: C14H12 Cl2 O2
• Molecular Weight: 283.154
• Mol File: 37580-81-7.mol
• Article Data: 124

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediol,1,2-bis(4-chlorophenyl)-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol,1,2-bis(4-chlorophenyl)-, (1R,2S)-rel-(37580-81-7)
• EPA Substance Registry System: 1,2-Ethanediol,1,2-bis(4-chlorophenyl)-, (1R,2S)-rel-(37580-81-7)

Safety Data

• Hazardous Substances Data: 37580-81-7(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 3218-36-8 4-Phenylbenzaldehyde 
• 66-99-9 β-naphthaldehyde 
• 105-07-7 4-cyanobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 3457-46-3 4,4'-dichlorobenzil 
• 1507365-51-6 C₁₇H₁₆Cl₂O₂ 
• 67-56-1 methanol 
• 2510-74-9 (E)-1,2-di(4-chlorophenyl)ethene 
• 106-95-6 allyl bromide 
• 78-94-4 methyl vinyl ketone 
• 4254-20-0 4,4'-dichlorobenzoin 
• 556-56-9 allyl iodid 
• 38152-42-0 1,2-bis(trimethylsiloxy)-1,2-bis(4'-chlorophenyl)ethane 

Downstream Products

• 18164-50-6 2,2-bis(4-chlorophenyl)acetaldehyde 
• 3457-46-3 4,4'-dichlorobenzil 
• 104-88-1 4-chlorobenzaldehyde 
• 74-11-3 para-chlorobenzoic acid 
• 23851-46-9 bis(4-chlorophenyl)(hydroxy)acetic acid 
• 1360546-72-0 4-(4-chlorophenyl)pyrrolo[1,2-a]quinoxaline 
• 325811-01-6 (S,S)-(-)-1,2-di(p-chlorophenyl)ethane-1,2-diol 
• 67111-67-5 (R,R)-(+)-1,2-bis(4-chlorophenyl)ethane-1,2-diol 
• 138476-26-3 2,3-bis(4-chlorophenyl)quinoxaline 
• 21711-56-8 4,4′′-dichloro-o-terphenyl 
• 5948-71-0 4-(4-chlorophenyl)-5-(ethoxycarbonyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 
• 5496-32-2 2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole 

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.

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Photocatalytic pinacol C-C coupling and jet fuel precursor production on ZnIn2S4nanosheets

Visible light-driven C-C bond formation has attracted increasing attention recently, thanks to the advance in molecular photosensitizers and organometallic catalysts. Nevertheless, these homogeneous methodologies typically necessitate the utilization of noble metal-based (e.g., Ir, Ru, etc.) photosensitizers. In contrast, solid-state semiconductors represent an attractive alternative but remain less explored for C-C bond-forming reactions driven by visible-light irradiation. Herein, we report that photocatalytic pinacol C-C coupling of benzaldehyde to hydrobenzoin can be achieved on two-dimensional ZnIn2S4 nanosheets upon visible-light irradiation in the presence of a sacrificial electron donor (e.g., triethylamine). We further demonstrate that it is feasible to take advantage of both excited electrons and holes in irradiated ZnIn2S4 for C-C coupling reactions in the absence of any sacrificial reagent if benzyl alcohol is utilized as the starting substrate, maximizing the energy efficiency of photocatalysis and circumventing any byproducts. In this case, industrially important benzoin and deoxybenzoin are formed as the final products. More importantly, by judiciously tuning the photocatalytic conditions, we are able to produce either benzoin or deoxybenzoin with unprecedented high selectivity. The critical species during the photocatalytic process were systematically investigated with various scavengers. Finally, such a heterogeneous photocatalytic pinacol C-C coupling strategy was applied to produce a jet fuel precursor (e.g., hydrofuroin) from biomass-derived furanics (e.g., furfural and furfural alcohol), highlighting the promise of our approach in practical applications.