66715-31-9

Basic information

• Product Name: METHYL 2-ISOCYANOBENZOATE
• Synonyms: 2-METHOXYCARBONYLPHENYL ISOCYANIDE;METHYL 2-ISOCYANOBENZOATE;HANSA ISN-0533
• CAS NO: 66715-31-9
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Mol File: 66715-31-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 2-ISOCYANOBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-ISOCYANOBENZOATE(66715-31-9)
• EPA Substance Registry System: METHYL 2-ISOCYANOBENZOATE(66715-31-9)

Safety Data

• Hazardous Substances Data: 66715-31-9(Hazardous Substances Data)

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 109-94-4 formic acid ethyl ester 
• 79-22-1 methyl chloroformate 
• 183209-26-9 ortho-bromophenyl isocyanide 
• 41270-80-8 N-formylanthranilic acid methyl ester 

Downstream Products

• 106283-19-6 (S)-2-(2-(2-(2-(dimethylamino)benzamido)-N-methylacetamido)-3-methylbutanamido)benzoic acid 
• 1418290-30-8 2-(2-(2-(2-(dimethylamino)benzamido)-N-propylacetamido)-3-methylbutan-amido)benzoic acid 
• 1418290-31-9 2-(2-(N-benzyl-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoic acid 
• 1418290-32-0 2-(2-(2-(2-(dimethylamino)benzamido)-N-(4-fluorobenzyl)acetamido)-3-methylbutanamido)benzoic acid 
• 1418290-33-1 2-(2-(N-(4-chlorobenzyl)-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoic acid 
• 1418290-34-2 2-(2-(2-(2-(dimethylamino)benzamido)-N-phenethylacetamido)-3-methylbutanamido)benzoic acid 
• 1418290-22-8 methyl 2-(2-(2-(2-(dimethylamino)benzamido)-N-methylacetamido)-3-methyl-butanamido)benzoate 
• 1418290-25-1 methyl 2-(2-(2-(2-(dimethylamino)benzamido)-N-propylacetamido)-3-methyl-butanamido)benzoate 
• 1418290-26-2 methyl 2-(2-(N-benzyl-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoate 
• 1418290-27-3 methyl 2-(2-(2-(2-(dimethylamino)benzamido)-N-(4-fluorobenzyl)acetamido)-3-methylbutanamido)benzoate 
• 1418290-28-4 methyl 2-(2-(n-(4-chlorobenzyl)-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoate 
• 1418290-29-5 methyl 2-(2-(2-(2-(dimethylamino)benzamido)-N-phenethylacetamido)-3-methylbutanamido)benzoate 
• 491-36-1 4-Hydroxyquinazoline 

Relevant articles and documents

Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles

A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.

The multicomponent approach to N-methyl peptides: Total synthesis of antibacterial (-)-viridic acid and analogues

Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.

Synthesis of 4-hydroxy-3-quinolinecarboxylic acid derivatives by a condensation/cyclization sequence between o-isocyanobenzoates and magnesium enolates

Addition of magnesium ester and amide enolates, generated using an excess amount of a magnesium amide (from diisopropylamine and ethylmagnesium bromide), to o-isocyanobenzoates affords 4-hydroxy-3-quinolinecarboxylic esters and amides by a tandem Claisen-type condensation/cyclization sequence.