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

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

Downstream Products

• 3457-46-3 4,4'-dichlorobenzil 
• 104-88-1 4-chlorobenzaldehyde 
• 21711-56-8 4,4′′-dichloro-o-terphenyl 
• 1360546-72-0 4-(4-chlorophenyl)pyrrolo[1,2-a]quinoxaline 
• 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 
• 14399-20-3 7-(4-chlorophenyl)-7H-bis-[1]benzopyrano[4,3-b:3',4'-c]pyran-6,8-dione 
• 4254-20-0 4,4'-dichlorobenzoin 
• 136203-53-7 9-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-2H,5H-1,8-acridinedione 
• 2510-74-9 (E)-1,2-di(4-chlorophenyl)ethene 
• 23851-46-9 bis(4-chlorophenyl)(hydroxy)acetic acid 
• 74-11-3 para-chlorobenzoic acid 
• 67111-67-5 (R,R)-(+)-1,2-bis(4-chlorophenyl)ethane-1,2-diol 
• 325811-01-6 (S,S)-(-)-1,2-di(p-chlorophenyl)ethane-1,2-diol 

Relevant articles and documents

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

High level time-dependent density functional theory (TD-DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values reported for a few candidates has been used for assessing the level of theory. On the basis of the results obtained, new strongly reducing PCs [Eox(PC.+/PC*)=?2.1 – ?2.0 V vs SCE] were discovered. Through the computational study of structure-properties relationships, a number of coumarins derivatives have been synthesized and evaluated in the pinacol coupling of aldehydes as the model reaction. The new organic photoredox catalysts show experimental photophysical and electrochemical data in accordance with the ones predicted by calculation, with excited state reduction potentials surpassing those of highly reducing transition metal-based PCs. A careful investigation of their behavior as PC has revealed crucial issues that need to be taken into consideration in the general photoredox catalysis, shedding light on the use of these PC in the pinacol, as well as, in other photoredox reactions.

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.