14917-59-0

Basic information

• Product Name: Benzoyl azide, 4-bromo-
• Synonyms: Benzoylazide, p-bromo- (6CI,8CI); 4-Bromobenzoyl azide; p-Bromobenzoyl azide
• CAS NO: 14917-59-0
• Molecular Formula: C₇H₄BrN₃O
• Molecular Weight: 229.04
• Mol File: 14917-59-0.mol

Chemical Properties

• CAS DataBase Reference: Benzoyl azide, 4-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl azide, 4-bromo-(14917-59-0)
• EPA Substance Registry System: Benzoyl azide, 4-bromo-(14917-59-0)

Safety Data

• Hazard Codes: 3:
• Safety Statements: − and NOx. See also AZIDES." target="_blank">Explodes when heated above its melting point. When heated to decomposition it
• Hazardous Substances Data: 14917-59-0(Hazardous Substances Data)

Upstream product

• 13195-79-4 2,2-dibromo-1-(4-bromophenyl)ethan-1-one 
• 37975-18-1 1-(4-bromophenyl)-3-(4-methoxyphenyl)propane-1,3-dione 
• 33170-68-2 1,3-bis-(4-bromo-phenyl)-propane-1,3-dione 
• 50-00-0 formaldehyd 
• 589-87-7 1,4-bromoiodobenzene 
• 201230-82-2 carbon monoxide 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-76-5 4-Bromobenzoic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 5933-32-4 4-bromobenzoic acid hydrazide 

Downstream Products

• 25203-41-2 (4-bromo-phenyl)-carbamic acid furfuryl ester 
• 32767-01-4 N-acetyl-N'-(4-bromo-phenyl)-urea 
• 25203-35-4 1-propyl (4-bromophenyl)carbamate 
• 6269-49-4 2-isopropyl-5-methylphenyl (4-bromophenyl)carbamate 
• 57228-71-4 3-(4-bromo-phenylcarbamoyloxy)-cholest-5-ene 
• 100622-46-6 N-((4-bromophenyl)carbamoyl)benzamide 
• 86138-45-6 N-(4-bromo-phenyl)-N'-[1]naphthyl-urea 

Relevant articles and documents

Hypervalent iodine in synthesis. Part 54: One-step conversion of aryl aldehydes to aroyl azides using a combined reagent of (diacetoxyiodo)benzene with sodium azide

Aroyl azides are readily prepared from the corresponding aryl aldehydes with the aid of (diacetoxyiodo)benzene (DIB) and sodium azide in high yields. (C) 2000 Elsevier Science Ltd.

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement

Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.

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.

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.

Visible light sensitization of benzoyl azides: Cascade cyclization toward oxindoles: Via a non-nitrene pathway

Visible light sensitization of benzoyl azides was examined in reaction with N-phenylmethacrylamides to afford biologically important oxindoles and spirooxindoles via a cascade cyclization under mild reaction conditions. Mechanistic studies suggested a non-nitrene pathway, where triplet benzoyl azides act as the reactive intermediate.

Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles

An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).

The challenge of palladium-catalyzed aromatic azidocarbonylation: From mechanistic and catalyst deactivation studies to a highly efficient process

Azidocarbonylation of iodoarenes with CO and NaN3, a novel Heck-type carbonylation reaction, readily occurs in an organic solvent-H 2O biphasic system to furnish aroyl azides at room temperature and 1 atm. The reaction is catalyzed by Xantphos-Pd and exhibits high functional group tolerance. The catalyst deactivation product, [(Xantphos)PdI2], can be reduced in situ with PMHS to Pd(0) to regain catalytic activity. In this way, the catalyst loading has been lowered to 0.2% without any losses in selectivity at nearly 100% conversion to synthesize a series of aroyl azides in 80-90% isolated yield on a gram scale. Alternatively, the ArCON3 product can be used without isolation for further transformations in situ, e.g., to isocyanates, ureas, benzamides, and iminophosphoranes. A detailed experimental and computational study has identified two main reaction pathways for the reaction. For both routes, Ar-I oxidative addition to Pd(0) is the rate-determining step. In the presence of CO in excess, the Ar-I bond is activated by the less electron-rich Pd center of a mixed carbonyl phosphine complex. Under CO-deficient conditions, a slightly lower energy barrier pathway is followed that involves Ar-I oxidative addition to a more reactive carbonyl-free (Xantphos)Pd0 species. Mass transfer in the triphasic liquid-liquid-gas system employed for the reaction plays an important role in the competition between these two reaction channels, uniformly leading to a common aroyl azido intermediate that undergoes exceedingly facile ArCO-N 3 reductive elimination. Safety aspects of the method have been investigated.

Orthogonal reactivity of acyl azides in C-H activation: Dichotomy between C-C and C-N amidations based on catalyst systems

The dual reactivity of acyl azides was utilized successfully in C-H activation by the choice of catalyst systems: while selective C-C amidation was achieved under thermal Rh catalysis, a Ru catalyst was found to mediate direct C-N amidation also highly se

Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid-triphenylphosphine system

A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid-triphenylphosphine, is described.