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 
• 60-29-7 diethyl ether 
• 98-88-4 benzoyl chloride 
• 121-44-8 triethylamine 
• 93-97-0 benzoic acid anhydride 
• 20292-75-5 phenylglyoxal monohydrazone 
• 2009-96-3 2-diazo-1-phenylbutane-1,3-dione 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 100-47-0 benzonitrile 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 4079-52-1 methoxymethyl phenyl ketone 
• 101-41-7 benzeneacetic acid methyl ester 
• 108839-30-1 1,3-diphenyl-4-[2]pyridyl-azetidin-2-one 
• 20341-12-2 N-(2-benzo[1,3]dioxol-5-ylethyl)-2-phenylacetamide 
• 51527-45-8 (±)-trans-1-(4-methoxyphenyl)-3,4-diphenylazetidin-2-one 
• 51096-49-2 2-benzylamino-1-phenyl-ethanol 
• 5300-22-1 (R/S)-2-(ethylamino)-1-phenylethanol 
• 942-94-9 2-(N-propylamino)-1-phenylethanol 
• 15129-13-2 phenylacetylsemicarbazide 
• 40669-47-4 N-methyl-N,2-diphenylacetamide 
• 16141-49-4 trans-1,3,4-triphenyl-2-azetidinone 
• 67655-17-8 α-chloro-α-(phenylthio)acetophenone 
• 37622-86-9 3,5-dibenzoyl-1H-pyrazole 
• 1839-72-1 2-phenylbenzofuran 

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.

N-transfer reagent and method for preparing the same and its application

Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.

Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N?H Carbene Insertions

Implementing catalytic organometallic transformations in living settings can offer unprecedented opportunities in chemical biology and medicine. Unfortunately, the number of biocompatible reactions so far discovered is very limited, and essentially restricted to uncaging processes. Here, we demonstrate the viability of performing metal carbene transfer reactions in live mammalian cells. In particular, we show that copper (II) catalysts can promote the intracellular annulation of alpha-keto diazocarbenes with ortho-amino arylamines, in a process that is initiated by an N-H carbene insertion. The potential of this transformation is underscored by the in cellulo synthesis of a product that alters mitochondrial functions, and by demonstrating cell selective biological responses using targeted copper catalysts. Considering the wide reactivity spectrum of metal carbenes, this work opens the door to significantly expanding the repertoire of life-compatible abiotic reactions.