136340-96-0

Basic information

• Product Name: N-(2-bromophenyl)-2-thiophenecarboxamide
• Synonyms: N-(2-bromophenyl)-2-thiophenecarboxamide
• CAS NO: 136340-96-0
• Molecular Formula: C₁₁H₈BrNOS
• Molecular Weight: 282.15632
• Mol File: 136340-96-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-bromophenyl)-2-thiophenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-bromophenyl)-2-thiophenecarboxamide(136340-96-0)
• EPA Substance Registry System: N-(2-bromophenyl)-2-thiophenecarboxamide(136340-96-0)

Safety Data

• Hazardous Substances Data: 136340-96-0(Hazardous Substances Data)

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 615-36-1 2-bromoaniline 
• 3437-95-4 2-Iodothiophene 
• 201230-82-2 carbon monoxide 
• 527-72-0 2-thiophenylcarboxylic acid 

Downstream Products

• 1263914-04-0 {2-[(thiophene-2-carbonyl)amino]phenyl}phosphonic acid diethyl ester 
• 1263914-25-5 2-(thien-2-yl)-1H-1,3-benzazaphosphole 
• 1263914-29-9 C₁₁H₁₂NPS 

Relevant articles and documents

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water

The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.