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

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

1. Used in Pharmaceutical Industry:
1-BROMO-4-ISOCYANOBENZENE is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows for the formation of diverse molecules with potential therapeutic applications.
2. Used in Chemical Synthesis:
1-BROMO-4-ISOCYANOBENZENE is used as a building block in the synthesis of complex organic molecules, such as dyes, pigments, and polymers. Its reactivity with other compounds enables the creation of a wide range of products with different properties and applications.
3. Used in the Preparation of 4-Tetrazolyl substituted-Benzo[d][1,3]oxazine derivatives:
1-BROMO-4-ISOCYANOBENZENE is used as a reactant in the Passerini multi-component reaction, which is a versatile method for the synthesis of various heterocyclic compounds. The resulting 4-Tetrazolyl substituted-Benzo[d][1,3]oxazine derivatives have potential applications in various fields, including pharmaceuticals and materials science.

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

Upstream product

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

Downstream Products

• 1608155-12-9 N-(4-bromophenyl)-2-(7-bromo-9,9-diethylfluoren-2-yl)isoindole-1-carboxamide 
• 1174062-74-8 N-(4-bromophenyl)-2-phenylpropionamide 

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.

CuSO4-Catalyzed Tandem C(sp3)-H Insertion Cyclization of Toluenes with Isonitriles to Form Indoles

A CuSO4-catalyzed tandem benzylic C-H insertion cyclization of toluene derivatives and isonitriles is described. The naturally abundant salt CuSO4 serves as a low-cost ligand-free redox catalyst. This reaction provides a practical mo

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.

Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines

A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.

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.

Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides

The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.

Dramatically Enhanced Solubility of Halide-Containing Organometallic Species in Diiodomethane: The Role of Solvent???Complex Halogen Bonding

In the current study, we evaluated the solubility of a number of organometallic species and showed that it is noticeably improved in diiodomethane when compared to other haloalkane solvents. The better solvation properties of CH2I2 w

TEMPO-Catalyzed Aerobic Oxidative Selenium Insertion Reaction: Synthesis of 3-Selenylindole Derivatives by Multicomponent Reaction of Isocyanides, Selenium Powder, Amines, and Indoles under Transition-Metal-Free Conditions

A novel and efficient approach for the selenium functionalization of indoles was developed with selenium powder as the selenium source, catalyzed by 2,2,6,6-tetramethylpiperidinooxy (TEMPO) and employing O2 as the green oxidant. This protocol provides a practical route for the synthesis of 3-selenylindole derivatives and has the advantages of readily available starting materials, mild reaction conditions, and a wide scope of substrates. Electron spin-resonance (ESR) studies reveal that the approach involves the formation of nitrogen-centered radicals and selenium radicals via oxidation of in situ generated selenoates.

Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins

A new strategy for constructing indolizino[1,2-b]quinolin-9(11H)-ones (ring cores of camptothecins) from readily available isocyanoarenes and N-(alkyl-2-yn-1-yl)pyridin-2(1H)-ones has been developed through a visible-light-induced radical cascade cyclization process. The reaction proceeds under mild conditions with fair to excellent yields. The easy introduction of substituents for both reactants and the broad functional group tolerance of the reaction make it a straightforward route to the cores of the marketed camptothecins and their derivatives.

Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles

A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.