3469-17-8

Basic information

• Product Name: 1,2-Diphenyl-2-diazoethanone
• Synonyms: 1,2-Diphenyl-2-diazoethanone;2-Diazo-1,2-diphenylethanone;Azibenzil;Benzoylphenyldiazomethane;2-diazo-1,2-diphenylethan-1-one;2-Diazo-2-phenylacetophenone
• CAS NO: 3469-17-8
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 223.2494
• Mol File: 3469-17-8.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Diphenyl-2-diazoethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diphenyl-2-diazoethanone(3469-17-8)
• EPA Substance Registry System: 1,2-Diphenyl-2-diazoethanone(3469-17-8)

Safety Data

• Hazardous Substances Data: 3469-17-8(Hazardous Substances Data)

Usage

General Description

1,2-Diphenyl-2-diazoethanone is a chemical compound with the molecular formula C14H12N2O. It is a yellow solid that is sensitive to light and heat. 1,2-Diphenyl-2-diazoethanone is used in organic synthesis as a photochemical reagent, particularly in the formation of carbenes for the purpose of inserting into C-H and N-H bonds. It can be used to prepare various substituted porphyrins and porphyrin dendrimers. However, it is important to handle this compound with caution as it is a hazardous material and can pose health risks if not used properly.

InChI:InChI=1/C14H11N2O/c15-16-13(11-7-3-1-4-8-11)14(17)12-9-5-2-6-10-12/h1-10,15H/q+1

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 624-90-8 Methanesulfonyl azide 
• 5344-88-7 benzil monohydrazone 
• 71-43-2 benzene 
• 5344-88-7 (E)-2-hydrazono-1,2-diphenylethanone 
• 103-80-0 phenylacetyl chloride 
• 501-65-5 diphenyl acetylene 
• 947-91-1 Diphenylacetaldehyde 
• 88485-00-1 3-Amino-4-hydroxy-4,5-diphenyl-oxazolidin-2-one 
• 134-81-6 benzil 
• 574-16-3 (Z)-benzilmonooxime 
• 574-15-2 (E)-benzil monooxime 
• 68384-27-0 benzil mono(toluene-p-sulphonyl)hydrazone 
• 88485-01-2 3-amino-4,5-diphenyl-1,3-oxazolin-2-one 

Downstream Products

• 82508-00-7 1-benzyl-3,3,4-triphenyl-2-azetidinone 
• 24765-98-8 4-chlorophenyldiphenylacetamide 
• 103329-74-4 1-diphenylacetoxy-2-(2,2-diphenyl-acetylamino)-ethane 
• 70298-77-0 N-(4-nitrophenyl)-2,2-di-phenylacetamide 
• 106277-95-6 benzil-mono-(triphenylphosphoranylidene-hydrazone) 
• 19352-70-6 1,3,3,4-tetraphenylazetidin-2-one 
• 101611-77-2 1,2,4,4-tetraphenyl-[1,2]diazetidin-3-one 
• 26392-12-1 tetraphenyl-p-quinodimethane 
• 20736-40-7 2-(benzyloxy)-1,2-diphenylethanone 
• 60637-20-9 benzaldehyde N'-(3-methyl-3H-benzothiazol-2-ylidene)-N-oxy-hydrazone 
• 2892-39-9 diphenyl-acetic acid-(2,3,4-triphenyl-[1]naphthyl ester) 
• 3028-34-0 diphenylethanedione mono-[(tri-morpholin-4-yl-λ⁵-phosphanylidene)-hydrazone] 
• 14224-99-8 2-methyl-4,5-diphenyloxazole 
• 36966-43-5 Thiophosphoric acid O,O'-diethyl ester O''-(2-oxo-1,2-diphenyl-ethyl) ester 

Relevant articles and documents

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Reactions of α-diazoketones with indolinone imines: Synthesis of new 1,3,3-triaryl-1′-methylspiro[azetidine-2,3′-indoline]-2′, 4-diones

The paper describes the synthesis of new 1,3,3-triary-1′- methylspiro[azetidine-2,3′-indoline]-2′,4-diones from reaction of the 2-diazo-1,2-diarylethanones with 3-arylimino-1-methyl-2-indolinones. The compounds have been characterized by satisfactory anal

Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds

An efficient copper-catalyzed carbenoid insertion reaction of α-diazo carbonyl compounds into Si-H and S-H bonds was developed. A wide range of α-silylesters and α-thioesters was obtained in high yields (up to 98%) from α-diazoesters using 5 mol% of a simple copper(I) salt as catalyst. Using 0.05 mol% of the same catalyst, α-diazoketones led to α-silylketones in low to good yields (up to 70%).