22693-32-9

Basic information

• Product Name: Benzoyl azide, 4-methyl-
• CAS NO: 22693-32-9
• Molecular Formula: C8H7N3O
• Molecular Weight: 161.163
• Mol File: 22693-32-9.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: Benzoyl azide, 4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl azide, 4-methyl-(22693-32-9)
• EPA Substance Registry System: Benzoyl azide, 4-methyl-(22693-32-9)

Safety Data

• Hazardous Substances Data: 22693-32-9(Hazardous Substances Data)

Upstream product

• 25856-03-5 1-(4-methoxy-phenyl)-3-p-tolyl-propane-1,3-dione 
• 3594-36-3 1,3-bis(p-methylphenyl)-1,3-propanedione 
• 4974-59-8 2,2-dichloro-4'-methylacetophenone 
• 766-97-2 4-n-methylphenylacetylene 
• 50-00-0 formaldehyd 
• 624-31-7 4-tolyl iodide 
• 201230-82-2 carbon monoxide 
• 99-94-5 p-Toluic acid 
• 14189-19-6 ethyl 4-methylbenzoyl carbonate 
• 59046-28-5 p-toluoyl-1H-1,2,3-benzotriazole 
• 36106-76-0 2,4-dinitrophenyl 4-methylbenzoate 
• 874-60-2 4-methyl-benzoyl chloride 
• 3619-22-5 p-toluic hydrazide 

Downstream Products

• 5436-83-9 N-benzyl-4-methylbenzamide 
• 20553-99-5 N-(1-butyl-1λ⁵-phospholan-1-ylidene)-4-methyl-benzamide 
• 732-93-4 4-methyl-N-(4-methylbenzoyl)-benzamide 
• 19711-87-6 2-oxo-2-diphenyl-N-(p-tolyl)acetamide 
• 5602-96-0 methyl p-tolylcarbamate 
• 623-08-5 N-methyl-p-toluidine 
• 106-49-0 p-toluidine 
• 104825-43-6 4-methyl-N-(phenylcarbamoyl)benzamide 
• 67986-12-3 N-(p-tolyl)quinoxalin-2-amine 

Relevant articles and documents

Reactions of Primary Amines and Alcohols with 4-Toluoyl Azide

Primary amines 2 react with 4-toluoyl azide 1 in non-nucleophilic solvents in a clear second order reaction, which is strongly dependent on the size of the amine 2 and the solvent polarity (k2: 15.51 (2a), 0.83 (2b) and 0.19 (2c) l/mol*min; ΔH(excit.) = 22.1 kJ/mol, ΔS(excit.) = -170.5 J/mol*K ).Drastic changes occur in the presence of nucleophilic solvents.With nucleophilic amines 2 added to these in the solutions a concurrent reaction with alcohols 4 yielding 4-toluoyl ester 5 is observed.This is especially dominating with the "smallest" alcohol methanol (4a) and/or effectively promoted by "bulky" amines (2b, 2c; up to 99percent 5a).Compared with the pure alcoholysis a huge acceleration of the ester formation, proportional to the concentration of the nucleophilic amine 2, is observed.The reaction mechanism is discussed with special emphasis on steric effects in the competition of nucleophiles for the aroyl azide 1. - Keywords.Aroyl azide; 4-Toluoyl azide; Alcoholysis; Aminolysis; "Nucleophilic catalysis"; Kinetics; Steric effects.

An Improved Synthesis of Polyfunctional Acyl Azides in PEG 400

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Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition

A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.

Visible Light-Induced Regioselective Cycloaddition of Benzoyl Azides and Alkenes to Yield Oxazolines

Visible light catalysis allows the regioselective synthesis of oxazolines in high yields. The mild photosensitized manifold leverages the intermolecular formation of oxazolines with a wide functional group tolerance on both benzoyl azides and alkenes part