1-Isocyano-4-nitrobenzene

Base Information

• Chemical Name: 1-Isocyano-4-nitrobenzene
• CAS No.: 1984-23-2
• Molecular Formula: C7H4 N2 O2
• Molecular Weight: 148.121
• Hs Code.: 2926909090
• European Community (EC) Number: 811-116-3
• DSSTox Substance ID: DTXSID30173579
• Nikkaji Number: J103.277A
• Wikidata: Q83043633
• Mol file: 1984-23-2.mol

Synonyms:1-Isocyano-4-nitrobenzene;1984-23-2;4-Nitrophenylisocyanide;4-Nitrophenyl isocyanide;p-Nitrophenyl isocyanide;BENZENE, 1-ISOCYANO-4-NITRO-;p-Nitrophenyl isonitrile;Phenyl isocyanide, p-nitro-;Benzene, 1-isocyano-4-nitro- (9CI);p-nitro-phenyl isonitrile;SCHEMBL2273860;DTXSID30173579;MFCD01937394;STK505800;AKOS005144096;AS-59433;LS-30404;BB 0260542;N0982;Phenyl isocyanide, p-nitro- (6CI,7CI,8CI);E78827;EN300-1177058

Chemical Property of 1-Isocyano-4-nitrobenzene

Chemical Property:

• Melting Point: 95-97 °C
• PSA: 45.82000
• LogP: 1.89950
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 148.027277375
• Heavy Atom Count: 11
• Complexity: 192

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Nitrophenyl Isocyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#[N+]C1=CC=C(C=C1)[N+](=O)[O-]
• Uses: Agricultural chemical. 4-Nitrophenyl Isocyanide is used in preparation of piperazinedione derivatives for use as cardiac sarcomere inhibitors.

Technology Process of 1-Isocyano-4-nitrobenzene

There total 9 articles about 1-Isocyano-4-nitrobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

p-nitroformanilide (16135-31-2) → p-nitrophenyl isocyanide (1984-23-2)

Guidance literature:

With diisopropylamine; trichlorophosphate; In dichloromethane; at 0 - 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tet.2012.09.068

Reference yield: 47.0%

p-nitrophenylthiourea (3696-22-8) → p-nitrophenylurea (556-10-5) + p-nitrophenyl isocyanide (1984-23-2)

Guidance literature:

With cetyl-trimethylammonium dichromate; In acetonitrile; chemoselective reaction; Reflux;

DOI:10.1080/00397910903398684

Reference yield: 43.0%

chloroform (67-66-3,8013-54-5) + 4-nitro-aniline (100-01-6,104810-17-5) → p-nitrophenyl isocyanide (1984-23-2)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; chloroform; for 12h;

DOI:10.1016/S0040-4020(01)85980-9

upstream raw materials:

p-nitroformanilide

Diaethyl-<4-nitro-benz-syn-aldoximino>-orthopropionat

formic acid

4-nitro-aniline

Downstream raw materials:

2-Chloroquinoline

Ν-(4-nitrophenyl)quinoline-2-carboxamide

1-chloroisoquinoline

Cl(Bu₃P)2PtC(=NC₆H₄NO₂-p)C₄H₂SC(=NC₆H₄NO₂-p)Pt(PBu₃)2Cl

Refernces

• 1、 Zhao, Xue Zhi,Kiselev, Evgeny,Lountos, George T.,Wang, Wenjie,Tropea, Joseph E.,Needle, Danielle,Hilimire, Thomas A.,Schneekloth, John S.,Waugh, David S.,Pommier, Yves,Burke, Terrence R.. "Small molecule microarray identifies inhibitors of tyrosyl-DNA phosphodiesterase 1 that simultaneously access the catalytic pocket and two substrate binding sites". . p. 3876 - 3884. Retrieved 2021/04/02.
• 2、 Weidlich, Frauke,Esumi, Naoto,Chen, Dongyang,Mück-Lichtenfeld, Christian,Zysman-Colman, Eli,Studer, Armido. "Mild C?F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm". supporting information. p. 376 - 383. Retrieved 2019/11/19.