3282-32-4

Basic information

• Product Name: Diazoacetylbenzene
• Synonyms: 2-Diazo-1-phenylethanone;Benzoyldiazomethane;Diazoacetylbenzene;Diazomethyl(phenyl) ketone;α-Diazoacetophenone;.alpha.-Diazoacetophenone;.Omega.-diazoacetophenone;2-Diazoacetophenone
• CAS NO: 3282-32-4
• Molecular Formula: C₈H₆N₂O
• Molecular Weight: 146.16
• Mol File: 3282-32-4.mol
• Article Data: 82

Chemical Properties

• Melting Point: 49 °C
• Boiling Point: 265.75°C (rough estimate)
• Appearance: /
• Density: 1.2312 (rough estimate)
• Refractive Index: 1.4900 (estimate)
• CAS DataBase Reference: Diazoacetylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Diazoacetylbenzene(3282-32-4)
• EPA Substance Registry System: Diazoacetylbenzene(3282-32-4)

Safety Data

• Hazardous Substances Data: 3282-32-4(Hazardous Substances Data)

Usage

General Description

Diazoacetylbenzene, also known as phenyl diazothioacetate, is a chemical compound that exhibits diazo functionality. It is characterized by a phenyl ring connected to a diazo group, with an acetyl group attached to the diazo group. Diazoacetylbenzene is used as a reagent in organic synthesis, particularly in the formation of amides and esters. It is also utilized in the preparation of diazo dyes, which are used in the textile industry. However, it is important to handle diazoacetylbenzene with caution, as it is a potentially hazardous chemical due to its diazo functionality, which can be unstable and reactive under certain conditions.

InChI:InChI=1/C8H7N2O/c9-10-6-8(11)7-4-2-1-3-5-7/h1-6,9H/q+1

Upstream product

• 186581-53-3 diazomethane 
• 618-32-6 Benzoyl bromide 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 93-97-0 benzoic acid anhydride 
• 30091-47-5 3-(N-methylphenylamino)-1-phenylprop-2-en-1-one 
• 2009-96-3 2-diazo-1-phenylbutane-1,3-dione 
• 65-85-0 benzoic acid 
• 96845-66-8 2-diazo-1-phenyl-2-(triethylsilyl)ethanone 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 60190-80-9 dimethyl (1-diazo-2-oxo-2-phenylethyl)phosphonate 
• 120-46-7 1,3-diphenylpropanedione 
• 6327-79-3 1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 93-91-4 1-phenylbutan-1,3-dione 

Downstream Products

• 51527-45-8 (±)-trans-1-(4-methoxyphenyl)-3,4-diphenylazetidin-2-one 
• 2010-06-2 2-Amino-4-phenylthiazole 
• 948-65-2 2-phenyl-indole 
• 621-06-7 2,N-diphenylacetamide 
• 40669-47-4 N-methyl-N,2-diphenylacetamide 
• 102704-52-9 1-benzyl-4t-(4-nitro-phenyl)-3r-phenyl-azetidin-2-one 
• 23808-72-2 naphthalen-2-yl-(3-naphthalen-2-yl-4-phenyl-3H-thiazol-2-ylidene)-amine 
• 68395-80-2 2-tert-butyl-5-phenyl-1,3-oxazole 
• 61153-48-8 α-Fluor-α-trifluormethoxyacetophenon 
• 33925-37-0 Diphenyl-acetic acid 1-[1-diphenylacetoxy-1-phenyl-meth-(Z)-ylidene]-3-phenyl-1H-inden-2-yl ester 
• 22177-08-8 2-phenylamino-5-phenyl-6H-1,3,4-thiadiazine 
• 1465-11-8 [5-(3-chloro-anilino)-[1,2,3]thiadiazol-4-yl]-phenyl-methanone 
• 3969-09-3 2-methyl-5-phenyl-1,3-oxazole 
• 72012-34-1 2-methyl-3-(2-oxo-2-phenyl-ethyl)-5-phenyl-oxazolium; trifluoromethanesulfonate 

Relevant articles and documents

SYNTHESIS OF SILYLDIAZOKETONES FROM LITHIUM PENTAMETHYLDISILANYLDIAZOMETHANE WITH ACID CHLORIDES

Lithium pentamethyldisilanyldiazomethane, prepared from pentamethyldisilanyldiazomethane and lithium diisopropylamide, reacts with acid chlorides to give pentamethyldisilanyldiazoketones in good yields.

Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

The photoinduced, multicomponent reaction of α-diazoketones, silanols, and isocyanides affords α-silyloxy acrylamides, formally derived from α-keto amides. The presence of a secondary amido group makes classic preparative methods for silyl enol ethers unfeasible in this case, while the mild conditions required by this photochemical approach allow their synthesis in good yields; moreover, the general structure can be easily modified by varying each component of the multicomponent reaction. Fine-tuning of the reaction conditions (i.e., solvents, radiation, additives) can be exploited to obtain complete Z selectivity. The reactivity of this overlooked class of silyl enol ethers has been investigated, and features that could pave the way to new applications have been found.

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

Solvent-Directed Transition Metal-Free C-C Bond Cleavage by Azido-1,3,5-triazines and Their Stability-Reactivity Paradox

We report a solvent-directed and regioselective carbon-carbon bond cleavage of aryl ketones by azido-1,3,5-triazines (ATs), which is typically completed within 10 min in DMSO at room temperature, without using transition metal catalysts. The cleavage is driven by the steric hindrance in the adducts of aryl ketones and ATs, which is substantiated by DFT calculation. Our recent results showed that ATs present high reactivity in solution and high stability in solid state. This "stability-reactivity paradox"has been explained in light of the molecular and crystal structures of ATs.