21368-28-5

Basic information

• Product Name: 4-chlorobenzoyl azide
• Synonyms: 4-chlorobenzoyl azide
• CAS NO: 21368-28-5
• Molecular Formula: C₇H₄ClN₃O
• Molecular Weight: 181.57916
• Mol File: 21368-28-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-chlorobenzoyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorobenzoyl azide(21368-28-5)
• EPA Substance Registry System: 4-chlorobenzoyl azide(21368-28-5)

Safety Data

• Hazardous Substances Data: 21368-28-5(Hazardous Substances Data)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 13651-12-2 2,2-dibromo-1-(4-chlorophenyl)ethanone 
• 74-11-3 para-chlorobenzoic acid 
• 32792-54-4 2,4-dinitrophenyl 4-chlorobenzoate 
• 14189-18-5 4-Chlor-benzoesaeure-kohlensaeure-ethylester-anhydrid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 50-00-0 formaldehyd 
• 37975-19-2 1-(4-chlorophenyl)-3-(4-methoxyphenyl)propane-1,3-dione 
• 18362-49-7 1,3-bis(4-chlorophenyl)propane-1,3-dione 
• 100-46-9 benzylamine 
• 4231-70-3 p-chlorobenzoyl-1H-1,2,3-benzotriazole 

Downstream Products

• 32772-86-4 N-acetyl-N'-(4-chloro-phenyl)-urea 
• 92290-74-9 (4-chloro-phenyl)-carbamic acid p-tolyl ester 
• 85966-63-8 (4-chloro-phenyl)-carbamic acid-[1]naphthyl ester 
• 197514-02-6 N-(4-chloro-phenyl)-N'-(2,5-dimethyl-phenyl)-urea 
• 445008-79-7 N-(4-bromo-3-methyl-phenyl)-N'-(4-chloro-phenyl)-urea 
• 39618-23-0 1-(4-chlorophenyl)-3-(4-hydroxyphenyl)urea 
• 57160-46-0 N-((4-chlorophenyl)carbamoyl)benzamide 
• 13257-14-2 1-(4-chlorophenyl)-3-(naphthalen-1-yl)urea 
• 72802-46-1 N-(4-chlorophenyl)-N'-cyclohexylurea 
• 3815-63-2 3-(4-chlorophenyl)-1-(4-tolyl)urea 

Relevant articles and documents

One-step Conversion of Esters to Acyl Azides Using Diethylaluminum Azide

Diethylaluminum azide, prepared from either sodium azide and diethylaluminum chloride or hydrazoic acid and triethylaluminum, reacts with esters to yield acyl azides in one step.

Synthesis of acyl azides from carboxylic acids using cyanuric chloride

A mild, efficient and general method for the preparation of acyl azides from carboxylic acids and sodium azide using cyanuric chloride is described.

FeCl36H2O-Catalyzed acceleration of the acylation of sodium azide with n-acylbenzotriazoles

Catalyzed by ferric chloride hexahydrate (FeCl36H2O), the acylation of sodium azide with N-acylbenzotriazoles was greatly accelerated in a mixed solvent of acetone and water. Thus, good to excellent yields of a variety of acyl azides were obtained at room temperature in a short time. Furthermore, because of the complete conversion of N-acylbenzotriazoles and the easy removal of the by-product, purification by column chromatography was no longer required, which made the protocol suitable for large-scale preparation.

3,4,5-Trifluorobenzeneboronic acid: A mild and versatile catalyst for the one-pot synthesis of acyl azides from carboxylic acids

Acyloxyboron intermediates generated from carboxylic acids and 3,4,5-trifluorobenzeneboronic acid react with sodium azide to furnish the corresponding acyl azides in moderate to good yields.

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

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

Palladium-Catalyzed One-Pot Synthesis of N -Sulfonyl, N -Phosphoryl, and N -Acyl Guanidines

An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N -sulfonyl-, N -phosphoryl-, and N -acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.

Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides

A general protocol for iridium catalyzed direct C?H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).

Synthesis of Acyl Azides from 1,3-Diketones via Oxidative Cleavage of Two C-C Bonds

A metal-free PhI(OAc)2-mediated method for the synthesis of acyl azides through oxidative cleavage of 1,3-diketones is described. This method is shown to have a broad substrate scope, providing a useful tool for multiproduct synthesis in a single procedure. A possible reaction pathway is proposed based on mechanistic studies.

Copper-catalyzed N[sbnd]H/S[sbnd]H functionalization: A strategy for the synthesis of benzothiadiazine derivatives

A copper-mediated N[sbnd]S bond-forming reaction via N[sbnd]H/S[sbnd]H activation is described. This reaction occurs under mild conditions with high efficiency, step economy, and tolerates a wide variety of functional groups, providing an efficient means of accessing biologically important 1,2,4-benzothiadiazin-3(4H)-ones.