18462-35-6

Basic information

• Product Name: Benzene, 1-[(1E)-2-bromoethenyl]-4-nitro-
• CAS NO: 18462-35-6
• Molecular Formula: C8H6BrNO2
• Molecular Weight: 228.045
• Mol File: 18462-35-6.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(1E)-2-bromoethenyl]-4-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(1E)-2-bromoethenyl]-4-nitro-(18462-35-6)
• EPA Substance Registry System: Benzene, 1-[(1E)-2-bromoethenyl]-4-nitro-(18462-35-6)

Safety Data

• Hazardous Substances Data: 18462-35-6(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 75867-38-8 4-nitro-1-(trimethylsilylethynyl)benzene 
• 637-57-0 p-nitrocinnamic acid methyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 51738-10-4 2,2-dibromo-1-(4-nitrophenyl)ethene 
• 19922-82-8 2-bromo-1-(4-nitrophenyl)ethanol 
• 619-89-6 p-nitrocinnamic acid 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 35447-78-0 2,3-dibromo-3-(4-nitro-phenyl)-propionic acid 
• 6286-30-2 erythro-2,3-dibromo-3-phenylpropanoic acid 
• 14275-61-7 (E)-1,2-bis(tri-n-butylstannyl)ethene 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 18436-62-9 1-(2,2-Dimethoxyethyl)-4-nitro-benzene 
• 7214-55-3 (E)-(4-nitrostyryl)(phenyl)sulfane 
• 10035-10-6 hydrogen bromide 
• 1233923-54-0 trans-[Pd(CHCHC₆H₄NO₂)Br(bis(p-tolyl)methylphosphine)2] 
• 1233923-55-1 trans-[Pd(CHCHC₆H₄NO₂)Br(bis(4-fluorophenyl)methylphosphine)2] 
• 1233923-53-9 trans-[Pd(CHCHC₆H₄NO₂)Br(diphenylmethylphosphine)2] 
• 1187023-34-2 (E)-1-(3,3-difluoroprop-1-en-1-yl)-4-nitrobenzene 
• 100-13-0 4-nitrostyrene 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 62-23-7 4-nitro-benzoic acid 
• 31145-10-5 (Z)-4-nitrocinnamonitrile 
• 27892-88-2 (E)-4-nitrocinnamonitrile 
• 18462-38-9 (E)-1-nitro-4-(2-(phenylsulfonyl)vinyl)benzene 
• 1459-12-7 (p-nitrophenyl)acetaldehyde oxime 

Relevant articles and documents

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates

Pd-catalyzed difluoromethylation of di-, tri- or tetra-substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes. Vinyl fantasy: Pd-catalyzed difluoromethylation of di-, tri-, or tetra-substituted vinyl bromides, triflates, tosylates, and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.