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

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

Uses

Used in Pharmaceutical Industry:
1-CHLORO-4-ISOCYANOBENZENE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs and medicinal compounds.
Used in Dye Industry:
In the dye industry, 1-CHLORO-4-ISOCYANOBENZENE serves as an intermediate in the production of dyes. Its aromatic and isocyanide properties contribute to the formation of dyes with specific color characteristics and properties.
Used in Organic Compounds Synthesis:
1-CHLORO-4-ISOCYANOBENZENE is utilized as a key intermediate in the synthesis of other organic compounds. Its versatility in chemical reactions allows for the creation of a wide range of organic molecules for various applications, including materials science, agrochemicals, and specialty chemicals.

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> 
• 2771-67-7 N-dichloromethylene-4-chloroaniline 
• 104-12-1 p-chlorphenylisocyanate 
• 3696-23-9 N-(4-chlorophenyl)thiourea 

Downstream Products

• 623-03-0 4-Cyanochlorobenzene 
• 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 
• 129801-44-1 (Z)-2-(4-Chloro-phenyliminomethyleneamino)-3-(2-methoxy-phenyl)-acrylic acid ethyl ester 
• 129801-39-4 1-(4-Chloro-phenylamino)-5-methoxy-isoquinoline-3-carboxylic acid ethyl ester 
• 129801-37-2 1-(4-Chloro-phenylamino)-6,7-dimethoxy-isoquinoline-3-carboxylic acid ethyl ester 
• 90827-51-3 2-(4-Chlorphenyl)-1-(4-chlorphenylamino)-6-(4-methylphenyl)-5-(4-methylphenylamino)benzo<1,2-c:4,5-c'>dipyrrol-4,8(2H,6H)-dion 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 14223-48-4 p-chlorophenyl isoselenocyanate 
• 14815-23-7 C₇H₄ClF₂N 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 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 
• 85830-79-1 1,4-Bis(4-chlorphenylimino)-3,6-diphenyl-1H,4H-furo<3,4-c>furan 

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.

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

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.

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.

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.

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

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.

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.

Rational design and synthesis of 1,5-disubstituted tetrazoles as potent inhibitors of the MDM2-p53 interaction

Using the computational pharmacophore-based ANCHOR.QUERY platform a new scaffold was discovered. Potent compounds evolved inhibiting the protein-protein interaction p53-MDM2. An extensive SAR study was performed based on our four-point pharmacophore model

Development of an Industrial Process Based on the Groebke-Blackburn-Bienaymé Multicomponent Reaction: Efficient Preparation- of 3-Aminoimidazo[1,2-a]pyrazines

3-Aminoimidazo[1,2-a]pyrazine is an important scaffold that is found in many drugs. This scaffold is rapidly accessible through a Groebke-Blackburn-Bienaymé cyclisation starting from an aminopyrazine, an aldehyde and an isocyanide. A scale-up process of this multicomponent reaction has been achieved in high yield and with excellent purity. The scope and limitations of this process leading to various 3-aminoimidazo[1,2-a]pyrazines are disclosed.