935-16-0

Basic information

• Product Name: 1,4-DIISOCYANOBENZENE
• Synonyms: 4-ISOCYANOPHENYLISOCYANIDE;1,4-DIISOCYANOBENZENE;1,4-PHENYLENE DIISOCYANIDE;Benzene, 1,4-diisocyano- (9CI);(p-Phenylene)diisocyanide;p-Phenylenediisocyanide;1,4-Phenylene diisocyanide,1,4-Diisocyanobenzene;1,4-Phenylene diisocyanide 97%
• CAS NO: 935-16-0
• Molecular Formula: C₈H₄N₂
• Molecular Weight: 128.13
• Product Categories: ISONITRITE;Building Blocks;Chemical Synthesis;Isocyanides;Nitrogen Compounds;Organic Building Blocks
• Mol File: 935-16-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 160 °C (dec.)(lit.)
• Appearance: /
• CAS DataBase Reference: 1,4-DIISOCYANOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIISOCYANOBENZENE(935-16-0)
• EPA Substance Registry System: 1,4-DIISOCYANOBENZENE(935-16-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 935-16-0(Hazardous Substances Data)

Usage

General Description

1,4-Diisocyanobenzene is a chemical compound with the formula C8H4N2O2. It is a colorless to light yellow liquid that is used in the production of polymers and plastics, particularly polyurethane. It is a diisocyanate, meaning it contains two isocyanate functional groups, which are highly reactive and are used in the formation of polyurethane polymers. 1,4-Diisocyanobenzene is considered a hazardous chemical, as exposure to it can cause skin and eye irritation, respiratory issues, and allergic reactions. It is important to handle this chemical with caution and ensure proper safety measures are in place when working with it. Overall, 1,4-Diisocyanobenzene plays a vital role in the production of various polymer materials but requires careful handling due to its potential health risks.

InChI:InChI=1/C8H4N2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H

Upstream product

• 6262-22-2 N-(4-formylaminophenyl)formamide 
• 503-38-8 trichloromethyl chloroformate 
• 67-66-3 chloroform 
• 106-50-3 1,4-phenylenediamine 
• 69236-29-9 p-aminophenyl isocyanide 

Downstream Products

• 623-26-7 terephthalonitrile 
• 92883-93-7 3-(4-Isocyano-phenylimino)-N,N,N',N'-tetramethyl-cycloprop-1-ene-1,2-diamine 
• 145333-67-1 W(CO)5CNC₆H₄NCW(CO)5 
• 88314-34-5 {(NC)2C₆H₄FeC₂₀H₈N₄(C₆H₅)4*0.1C₆H₅Cl}(n) 
• 204860-72-0 [μ-(1,4-diisocyanobenzene)-2,3,9,10,16,17,23,24-octakis(pentyloxy)phthalocyaninato]ruthenium(II) 
• 851916-02-4 benzene-1,4-bis[aminomethylidene(bisphosphonic)] acid 
• 1620164-64-8 octaethyl benzene-1,4-bis[aminomethylidene(bisphosphonate)] 

Relevant articles and documents

Pyrimidazole-Based Covalent Organic Frameworks: Integrating Functionality and Ultrastability via Isocyanide Chemistry

Development of new chemistry to simultaneously meet the demands for topology, connectivity, and functionality is highly desired in the research area of covalent organic frameworks (COFs). We explore herein the isocyanide chemistry so as to establish a facile paradigm to integrate functionality and ultrastability in COFs. Using the representative Groebke-Blackburn-Bienaymé (GBB) reaction based on isocyanide chemistry, we are able to construct a series of pyrimidazole-based COFs in one step from isocyanide, aminopyridine, and aldehyde monomers. Diversified functionalities have been bottom-up integrated by the simple replacement of readily available 2-aminopyridine monomers. Meanwhile, the ubiquitous formation of fused imidazole rings within the frameworks has guaranteed their ultrastability. In view of the rich synthetic possibilities provided by isocyanide chemistry, we expect that this contribution opens up a new avenue toward the divergent construction of robust COFs for practical applications.

Mild C?F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm

Fluorinated compounds have become important in the fields of agrochemical industry, pharmaceutical chemistry and materials sciences. Accordingly, various methods for their preparation have been developed in the past. Fluorinated compounds can be accessed via conjugation with fluorinated building blocks, via C?H fluorination or via selective activation of perfluorinated compounds to give the partially fluorinated congeners. Especially the direct activation of C?F bonds, one of the strongest σ-bonds, still remains challenging and new strategies for C?F activation are desirable. Herein a method for the photochemical activation of aromatic C?F bonds is presented. It is shown that isonitriles selectively insert into aromatic C?F bonds while aliphatic C?F bonds remain unaffected. Mechanistic studies reveal the reaction to proceed via the indirect excitation of the isonitrile to its triplet state by photoexcited acetophenone at 350 nm. Due to the relatively mild light used, the process shows high functional group tolerance and various compounds of the class of benzimidoyl fluorides are accessible from aryl isonitriles and commercially available perfluorinated arenes. (Figure presented.).

Novel synthetic route to allyl cyanamides: Palladium-catalyzed coupling of isocyanides, allyl carbonate, and trimethylsilyl azide [6]

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