27739-61-3

Basic information

• Product Name: 1-Butanone, 2-hydroxy-1,2-diphenyl-
• CAS NO: 27739-61-3
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• Mol File: 27739-61-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-Butanone, 2-hydroxy-1,2-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanone, 2-hydroxy-1,2-diphenyl-(27739-61-3)
• EPA Substance Registry System: 1-Butanone, 2-hydroxy-1,2-diphenyl-(27739-61-3)

Safety Data

• Hazardous Substances Data: 27739-61-3(Hazardous Substances Data)

Usage

General Description

1-Butanone, 2-hydroxy-1,2-diphenyl- is a chemical compound that belongs to the ketone family. It is also known as benzophenone hydrazone and is widely used as a reactant in organic synthesis and as a photoinitiator in the production of polymer coatings and adhesives. 1-Butanone, 2-hydroxy-1,2-diphenyl- has a diphenylmethanone backbone with a hydroxyl group and a 1-butanone substituent. It is a yellow crystalline solid at room temperature and is often used as a UV absorber in sunscreen formulations and as an antioxidant in plastics and rubber products. This chemical also has potential pharmaceutical applications, particularly in the development of anti-cancer drugs and photodynamic therapy.

Upstream product

• 76496-47-4 (S)-2-hydroxy-2-phenyl-butyric acid methyl ester 
• 16282-16-9 1,2-diphenyl-butan-1-one 
• 144786-54-9 (S)-2-hydroxy-2-phenylbutanamide 
• 557-20-0 diethylzinc 
• 134-81-6 benzil 
• 611-73-4 Benzoylformic acid 
• 76142-48-8 2-hydroxy-2-phenylbutyric acid methyl ester 
• 35468-69-0 2-hydroxy-2-phenylbutanoic acid 
• 30935-14-9 1,2-diphenyl-1,2-butanediol 
• 925-90-6 ethylmagnesium bromide 
• 557-18-6 diethylmagnesium 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 75-03-6 ethyl iodide 
• 52839-87-9 HEPA 

Downstream Products

• 54444-11-0 cis-2-phenyl-3-methylindanone 
• 79999-03-4 1,2,4-triphenyl-3-methylhexane-1,5-dione 
• 79999-01-2 2,4-dimethyl-3,5,6-triphenylpyridine 
• 54444-14-3 (Z)-1,2-diphenylbut-2-en-1-one 
• 38384-58-6 (E)-1-benzoyl-1-phenylprop-1-ene 

Relevant articles and documents

Reactions of ZnR2 compounds with dibenzoyl: Characterisation of the alkyl-transfer products and a striking product-inhibition effect

The first systematic theoretical and experimental studies of reaction systems involving ZnR2 (R=Me, Et or tBu) with dibenzoyl (dbz) as a non-innocent ligand revealed that the character of the metal-bonded R group as well as the ratio of the reagents and the reaction temperature significantly modulate the reaction outcome. DFT calculations showed four stable minima for initial complexes formed between ZnR2 and dbz and the most stable structure proved to be the 2:1 adduct; among the 1:1 adducts three structural isomers were found of which the most stable complex had the monodentate coordination mode and the chelate complex with the s-cis conformation of the dbz unit appeared to be the least stable form. Interestingly, the reaction involving ZnMe2 did not lead to any alkylation product, whereas the employment of ZntBu2 resulted in full conversion of dbz to the O-alkylated product [tBuZn{PhC(O)C(OtBu)Ph}] already at -20-°C. A more complicated system was revealed for the reaction of dbz with ZnEt2. Treatment of a solution of dbz in toluene with one equivalent of ZnEt 2 at room temperature afforded a mixture of the O- and C-alkylated products [EtZn{PhC(O)C(OEt)Ph}] and [EtZn{OC(Ph)C(O)(Et)Ph}], respectively. The formation of the C-alkylated product was suppressed by decreasing the initial reaction temperature to -20-°C. Moreover, in the case of the dbz/ZnEt 2 system monitoring of the dbz conversion over the entire reaction course revealed a product inhibition effect, which highlights possible participation of multiple equilibria of different zinc alkoxide/ZnEt2 aggregates. Diffusion NMR studies indicated that dbz forms an adduct with the O-alkylated product, which is a competent species for executing the inhibition of the alkylation event. It all depends on R: The first systematic theoretical and experimental study of ZnR2 (R=Me, Et or tBu) with dibenzoyl revealed that the character of the metal-bonded alkyl group as well as the reaction conditions (e.g., ratio of the reagents, temperature) modulate the reaction outcome (see scheme). Monitoring the dibenzoyl conversion over the reaction course revealed a product-inhibition effect, which highlights possible participation of multiple equilibria of different zinc alkoxide/ZnR2 aggregates.

Rearrangement of N- tert-Butanesulfinyl Enamines for Synthesis of Enantioenriched α-Hydroxy Ketone Derivatives

Treating chiral N-tert-butanesulfinyl ketimines with potassium hexamethyldisilazide (or potassium tert-butoxide) and methyl triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford α-sulfenyloxy ketones with excellent enantiopurities. This cascade of enamination-N-methylation-rearrangement was even used to generate acyclic tertiary α-hydroxy ketones bearing two α-substituents showing negligible differences in bulkiness, such as methyl and ethyl groups.

Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions

A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.