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

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

Uses

Used in Organic Synthesis:
Diazoacetylbenzene is used as a reagent in organic synthesis for the formation of amides and esters. Its diazo functionality allows for various chemical reactions that are crucial in the synthesis of complex organic compounds.
Used in the Textile Industry:
In the textile industry, Diazoacetylbenzene is utilized in the preparation of diazo dyes. These dyes are important for coloring fabrics and textiles, providing a wide range of color options and enhancing the aesthetic appeal of the products.
Safety Considerations:
It is important to handle Diazoacetylbenzene with caution, as it is a potentially hazardous chemical. Its diazo functionality can be unstable and reactive under certain conditions, necessitating proper safety measures during its use and storage.

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 
• 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 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 53580-21-5 4,4,5,5,6,6,6-heptafluoro-1-phenyl-hexane-1,3-dione 
• 100-47-0 benzonitrile 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 98-86-2 acetophenone 
• 30091-47-5 3-(N-methylphenylamino)-1-phenylprop-2-en-1-one 

Downstream Products

• 779-52-2 1-phenyl-2-piperidin-1-yl-ethanone 
• 495-71-6 phenacylacetophenone 
• 4079-52-1 methoxymethyl phenyl ketone 
• 101-41-7 benzeneacetic acid methyl ester 
• 5633-67-0 1,2,3-tribenzoylcyclopropane 
• 5369-54-0 2,4,2',4'-tetraphenyl-2H,2'H-[2,2']bifuranyl-5,5'-dione 
• 108839-30-1 1,3-diphenyl-4-[2]pyridyl-azetidin-2-one 
• 37552-67-3 3r,4t-diphenyl-1-p-tolyl-azetidin-2-one 
• 103646-24-8 4-ethylmercapto-5-phenyl-3H-oxazole-2-thione 
• 611-71-2 MANDELIC ACID 
• 1843-12-5 2,2'-imino-bis-4,4'-diphenylthiazole 
• 56462-63-6 N'-(4-chloro-phenyl)-2-oxo-2-phenyl-acetohydrazonoyl chloride 
• 73312-79-5 azulen-5-yl-phenyl ketone 
• 51527-50-5 1,3,4,4-tetraphenyl-azetidin-2-one 

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.

Three-component synthesis of fluorinated pyrazoles from fluoroalkylamines, NaNO2 and electron-deficient alkynes

Three-component reaction between RCF2CH2NH2·HCl, NaNO2 and electron-deficient alkynes significantly depends on substituent R . The reaction gives the fluorinated pyrazoles in high yields when R is a fluorine atom or a fluoroalkyl group. With other R unexpected products are formed.

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.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

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%).

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.

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.

Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion

The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.