113365-36-9

Basic information

• Product Name: Benzonitrile, 4,4'-(1,2-dihydroxy-1,2-ethanediyl)bis-
• CAS NO: 113365-36-9
• Molecular Formula: C16H12N2O2
• Molecular Weight: 264.283
• Mol File: 113365-36-9.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4,4'-(1,2-dihydroxy-1,2-ethanediyl)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4,4'-(1,2-dihydroxy-1,2-ethanediyl)bis-(113365-36-9)
• EPA Substance Registry System: Benzonitrile, 4,4'-(1,2-dihydroxy-1,2-ethanediyl)bis-(113365-36-9)

Safety Data

• Hazardous Substances Data: 113365-36-9(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 105-07-7 4-cyanobenzaldehyde 
• 359792-06-6 1-(tert-Butyldimethylsiloxy)-1-phenylselanyl-2-methyl-1-propene 
• 77078-44-5 Trimethyl-(2-methyl-1-methylsulfanyl-propenyloxy)-silane 
• 145279-03-4 1-(tert-butylthio)-2-methyl-1-(trimethylsilyloxy)prop-1-ene 
• 556-56-9 allyl iodid 
• 17314-40-8 3-Methyl-2-butenyl-trimethylstannane 
• 619-65-8 4-cyanobenzoic Acid 

Downstream Products

• 105-07-7 4-cyanobenzaldehyde 
• 619-65-8 4-cyanobenzoic Acid 

Relevant articles and documents

EFFICIENT FORMATION OF PINACOLS FROM ALDEHYDES OR KETONES MEDIATED BY SAMARIUM DIIODIDE

Samarium diiodide is an excellent reagent for aldehyde or ketone coupling.With aromatic aldehydes, reactions are very fast with a complete selectivity versus substituents such as cyano, carbonyl or nitro groups.

Reductive coupling of aromatic aldehydes promoted by an aqueous TiCl 3/tBuOOH system in alcoholic cosolvents

The tert-butoxyl radical, generated by the aqueous TiIII/TBHP system, abstracts an H atom from alcoholic cosolvents (EtOH, iPrOH), leading to α-hydroxyalkyl radicals that reduce aromatic aldehydes to the corresponding 1,2-diols. The reactivities observed are explained by resonance stabilization of the α-hydroxybenzyl radicals formed in the electron-transfer (ET) process. Good Hammett-type correlations are obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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.

Application of coumarin dyes for organic photoredox catalysis

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.

Transition-metal-free and chemoselective NaOtBu-O 2-mediated oxidative cleavage reactions of vic-1,2-diols to carboxylic acids and mechanistic insight into the reaction pathways

A method for efficient oxidative cleavage of vic-1,2-diols using a NaO tBu-O2 system resulted in the formation of carboxylic acids in high yields. The present protocol is an eco-friendly alternative to a conventional transition-metal-based method. This new strategy allows large-scale production with nonchromatographic purification while also suppressing competitive reaction pathway such as benzilic acid rearrangement.