1885-81-0

Basic information

• Product Name: 1-CHLORO-4-ISOCYANOBENZENE
• Synonyms: BIO-FARMA BF001949;HANSA ISN-0726;4-CHLOROPHENYL ISOCYANIDE;4-CHLORPHENYLISOCYANIDE;1-CHLORO-4-ISOCYANOBENZENE;Benzene, 1-chloro-4-isocyano- (9CI);Chlorophenylisocyanate (3,4 -isomer);p-Chlorophenyl isocyanide
• CAS NO: 1885-81-0
• Molecular Formula: C₇H₄ClN
• Molecular Weight: 137.57
• Product Categories: ISONITRITE
• Mol File: 1885-81-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 71-75 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 1-CHLORO-4-ISOCYANOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-4-ISOCYANOBENZENE(1885-81-0)
• EPA Substance Registry System: 1-CHLORO-4-ISOCYANOBENZENE(1885-81-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1885-81-0(Hazardous Substances Data)

Usage

General Description

1-CHLORO-4-ISOCYANOBENZENE is a compound with the chemical formula C7H4ClNO. It belongs to the class of aromatic isocyanides, which are molecules containing an isocyanide group (-N≡C) attached to an aromatic ring. This chemical is used as an intermediate in the production of pharmaceuticals, dyes, and other organic compounds. It is a highly reactive compound that is sensitive to moisture and air, and should be handled with care. 1-CHLORO-4-ISOCYANOBENZENE has the potential to cause skin and eye irritation, and can also be harmful if inhaled or ingested. Therefore, proper safety precautions should be taken when handling this chemical.

InChI:InChI=1/C7H4ClN/c1-9-7-4-2-6(8)3-5-7/h2-5H

Upstream product

• 2617-79-0 N-(4-chlorophenyl)formamide 
• 67-66-3 chloroform 
• 106-47-8 4-chloro-aniline 
• 34070-24-1 Dichlormethansulfonsaeure-<4-chlor-anilid> 
• 104-12-1 p-chlorphenylisocyanate 
• 3696-23-9 N-(4-chlorophenyl)thiourea 
• 2771-67-7 N-dichloromethylene-4-chloroaniline 

Downstream Products

• 623-03-0 4-Cyanochlorobenzene 
• 74739-70-1 [1-Aziridin-1-yl-meth-(Z)-ylidene]-(4-chloro-phenyl)-amine 
• 74739-82-5 (4-Chloro-phenyl)-[1-pyrrolidin-1-yl-meth-(Z)-ylidene]-amine 
• 74755-78-5 (4-Chloro-phenyl)-[1-piperidin-1-yl-meth-(Z)-ylidene]-amine 
• 99948-63-7 (4-Chloro-phenyl)-[2,5-di-tert-butyl-[1,4,2]dioxazolidin-(3Z)-ylidene]-amine 
• 74739-59-6 N'-(4-Chloro-phenyl)-N,N-diethyl-formamidine 
• 13463-94-0 N-(4-chlorophenyl)cyanamide 
• 935756-14-2 5-chloro-1-[3,3-diethyl-2-oxo-1-(p-chlorophenyl)azetidin-4-yl]-2-[(Z)-3,3-diethyl-2-oxo-1-(p-chlorophenyl)azetidin-4-ylidene]-3-(p-chlorophenylimino)-2,3-dihydroindole 
• 935756-12-0 5-chloro-1-[3,3-diethyl-2-oxo-1-(p-methoxyphenyl)azetidin-4-yl]-2-[(Z)-3,3-diethyl-2-oxo-1-(p-methoxyphenyl)azetidin-4-ylidene]-3-(p-chlorophenylimino)-2,3-dihydroindole 
• 935756-18-6 5-chloro-1-[3,3-diphenyl-2-oxo-1-(p-tolyl)azetidin-4-yl]-2-[(Z)-3,3-diphenyl-2-oxo-1-(p-tolyl)azetidin-4-ylidene]-3-(p-chlorophenylimino)-2,3-dihydroindole 
• 935756-22-2 8-chloro-1-(p-chlorophenyl)-3,3-dimethyl-4-phenylimino-5-(3,3-dimethyl-1-phenylazetidin-2-on-4-yl)-δ-carbolin-2-one 
• 935756-03-9 5-chloro-1-(3,3-dimethyl-2-oxo-1-phenylazetidin-4-yl)-2-((Z)-3,3-dimethyl-2-oxo-1-phenylazetidin-4-ylidene)-3-(p-chlorophenylimino)-2,3-dihydroindole 

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.

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

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.