33554-73-3

Basic information

• Product Name: 1-BROMO-4-ISOCYANOBENZENE
• Synonyms: 4-BROMOPHENYLISOCYANIDE;4-BROMPHENYLISOCYANIDE;1-BROMO-4-ISOCYANOBENZENE;BIO-FARMA BF000616;HANSA ISN-0517;Benzene, 1-bromo-4-isocyano- (9CI)
• CAS NO: 33554-73-3
• Molecular Formula: C₇H₄BrN
• Molecular Weight: 182.02
• Product Categories: ISONITRITE
• Mol File: 33554-73-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 98 °C(Solv: hexane (110-54-3))
• Appearance: /
• CAS DataBase Reference: 1-BROMO-4-ISOCYANOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-4-ISOCYANOBENZENE(33554-73-3)
• EPA Substance Registry System: 1-BROMO-4-ISOCYANOBENZENE(33554-73-3)

Safety Data

• Hazardous Substances Data: 33554-73-3(Hazardous Substances Data)

Usage

Uses

4-bromophenyl isocyanide is used in preparation of 4-Tetrazolyl substituted-Benzo[d][1,3]oxazine derivatives by Passerini multi-component reaction.

InChI:InChI=1/C7H4BrN/c1-9-7-4-2-6(8)3-5-7/h2-5H

Upstream product

• 2666-65-1 N-dichloromethylene-4-bromoaniline 
• 106-40-1 4-bromo-aniline 
• 2617-78-9 N-(4-bromophenyl)formamide 

Downstream Products

• 33787-91-6 (Z)-3-((4-bromophenyl)amino)-2-phenylacrylonitrile 

Relevant articles and documents

Design, synthesis and anticancer evaluation of 3-methyl-1H-indazole derivatives as novel selective bromodomain-containing protein 4 inhibitors

Bromodomain-containing Protein 4 (BRD4), an ‘epigenetic reader’, regulates chromatin structure and gene expression via recognizing and binding acetylated lysine in histones. BRD4 has become a therapeutic target for cancers because it promotes the expression of the tumor genes, such as c-Myc, NF-κB, and Bcl-2. In this study, a new series of 3-methyl-1H-indazole derivatives were designed via virtual screening and structure-based optimization. All compounds were synthesized and evaluated for their inhibitory activities to BRD4-BD1 and their antiproliferative effects in cancer cell lines. Among them, several compounds (such as 9d, 9u and 9w) exhibited strong BRD4-BD1 affinities and inhibition activities, and potently suppressed MV4;11 cancer cell line proliferation. Among them, compound 9d showed excellent selectivity for BRD4 and effectively suppressed c-Myc, the downstream protein of BRD4. This study provided new lead compounds for further biological evaluation on BRD4.

Silver-Catalyzed Selective Multicomponent Coupling Reactions of Arynes with Nitriles and Isonitriles

Pathway selective aryne-based novel multicomponent coupling reactions with isonitriles and nitriles are described. Crucial to these reactions is the formation of a silver-aryne complex, which shows differential reactivity toward isonitriles and nitriles to form two different forms of ortho-nitrilium organosilver arene species. Interception of the nitrilium of an aryne-isonitrile adduct with another isonitrile leads to the formation of benzocyclobutene-1,2-diimines, whereas the nitrilium of an aryne-nitrile adduct renders selective formation of 3H-indol-3-imines or 3-iminoindolin-2-ol depending on the structure of the nitrile employed.

Synthesis of Imides, Imidates, Amidines, and Amides by Intercepting the Aryne-Isocyanide Adduct with Weak Nucleophiles

New aryne-based multicomponent coupling reactions for the formation of functionalized aromatic compounds have been developed. Arynes generated from triynes or tetraynes through the hexadehydro Diels-Alder reaction readily react with isocyanide to generate nitrilium intermediate. Intercepting this nitrilium species with various weak nucleophile including carboxylic acids, alcohols, sulfonamides, or water generated the corresponding imides, imidates, amidines, or amides. The high regioselectivity of these transformations was mainly controlled by the substituents of the arynes.