198476-21-0

Basic information

• Product Name: Benzoic acid, 4-isocyano-, methyl ester (9CI)
• Synonyms: Benzoic acid, 4-isocyano-, methyl ester (9CI)
• CAS NO: 198476-21-0
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.15738
• Product Categories: ISONITRITE
• Mol File: 198476-21-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 4-isocyano-, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-isocyano-, methyl ester (9CI)(198476-21-0)
• EPA Substance Registry System: Benzoic acid, 4-isocyano-, methyl ester (9CI)(198476-21-0)

Safety Data

• Hazardous Substances Data: 198476-21-0(Hazardous Substances Data)

Upstream product

• 53405-05-3 N-formyl p-aminobenzoic acid methyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 
• 63450-84-0 methyl 4-aminobenzoate hydrochloride 

Downstream Products

• 198476-56-1 trans-[CoI₂(methyl-4-isocyanobenzoate)4] 
• 198476-44-7 trans-[FeI₂(methyl-4-isocyanobenzoate)4] 
• 198476-61-8 trans-[PdI₂(methyl-4-isocyanobenzoate)2] 
• 1303995-86-9 methyl 4-[(1,3-benzothiazol-2-yl)amino]benzoate 
• 1430217-51-8 (E)-methyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoate 
• 1430216-12-8 (E)-4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid 
• 1430216-32-2 C₂₉H₂₅ClN₆O₄ 

Relevant articles and documents

Multicomponent Synthesis and Binding Mode of Imidazo[1,2- a]pyridine-Capped Selective HDAC6 Inhibitors

The multicomponent synthesis of a mini-library of histone deacetylase inhibitors with imidazo[1,2-a]pyridine-based cap groups is presented. The biological evaluation led to the discovery of the hit compound MAIP-032 as a selective HDAC6 inhibitor with promising anticancer activity. The X-ray structure of catalytic domain 2 from Danio rerio HDAC6 complexed with MAIP-032 revealed a monodentate zinc-binding mode.

A more sustainable and highly practicable synthesis of aliphatic isocyanides

Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.

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.