39687-95-1

Basic information

• Product Name: METHYL ISOCYANOACETATE
• Synonyms: Methyl isocyanoacetate, technical grade;Methyl isocyanoacetate, 95%, tech.;(2-Oxo-2-methoxyethyl) isocyanide;2-Isocyanoacetic acid methyl ester;2-Oxo-2-methoxyethyl isocyanide;Methyl 2-isocyanoacetate;Acetic acid, 2-isocyano-, Methyl ester;Methyl isocyanoacetate, tech., 95% 5GR
• CAS NO: 39687-95-1
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• EINECS: 254-593-8
• Product Categories: Naphthyridine,Quinoline;Isocyanides;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;straight chain compounds;pharmacetical
• Mol File: 39687-95-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 75-76 °C10 mm Hg(lit.)
• Flash Point: 193 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 11.4mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: −20°C
• Water Solubility: Miscible with organic solvents. Slightly miscible with water.
• BRN: 3537963
• CAS DataBase Reference: METHYL ISOCYANOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL ISOCYANOACETATE(39687-95-1)
• EPA Substance Registry System: METHYL ISOCYANOACETATE(39687-95-1)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• F: 8-9-32-13-19
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 39687-95-1(Hazardous Substances Data)

Usage

Description

Methyl isocyanoacetate is a clear yellow to brown liquid that is utilized in various chemical reactions and synthesis processes. It is known for its involvement in the copper-catalyzed, diastereoselective synthesis of oxazolines, direct aldol reactions with carbonyl compounds, and participation in four-component Ugi condensation reactions.

Uses

Used in Chemical Synthesis:
Methyl isocyanoacetate is used as a reactant in the copper-catalyzed, diastereoselective synthesis of oxazolines for creating complex molecular structures with specific stereochemistry.
Used in Pharmaceutical Industry:
Methyl isocyanoacetate is used as a reactant in the direct aldol reaction with carbonyl compounds, facilitated by a solid-phase catechol-copper network catalyst, to yield corresponding oxazolines. These oxazolines are valuable intermediates in the development of pharmaceutical compounds.
Used in Organic Chemistry:
Methyl isocyanoacetate is used as a reactant in the four-component Ugi condensation reaction, which is a powerful method for the synthesis of diversely functionalized amines and their derivatives.
Used in Asymmetric Aldol Reactions:
Methyl isocyanoacetate is used as a reactant in asymmetric aldol reactions with fluorinated benzaldehyde, employing gold(I) as a catalyst. This reaction contributes to the synthesis of enantioenriched building blocks for various applications, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C4H7NO2/c1-5-3-4(6)7-2/h1,3H2,2H3

Upstream product

• 3154-54-9 methyl N-formylglycinate 
• 63857-17-0 methyl 3-oxopropionate 
• 58948-98-4 potassium 2-isocyanoacetate 

Downstream Products

• 71707-55-6 5-(2-methoxycarbonyl-4-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 71707-56-7 5-(2-methoxycarbonyl-5-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 71706-53-1 5-(2-methoxycarbonyl-6-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 72030-81-0 dimethyl oxazole-4,5-dicarboxylate 
• 62175-50-2 5-(2-acetylamino-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 62175-52-4 5-(2-acetylamino-5-methyl-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 62175-54-6 5-(2-propionylamino-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 62175-53-5 5-(2-acetylamino-5-chloro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 62175-51-3 5-(2-acetylamino-5-methoxy-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 38061-20-0 4-methoxycarbonyl-5-(3,4,5-trimethoxyphenyl)-oxazole 
• 72030-91-2 5,5'-p-phenylene-bis-oxazole-4-carboxylic acid dimethyl ester 
• 63348-60-7 N-benzyl-2-isocyanoacetamide 
• 53855-59-7 5-(2-acetoxy-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 72030-88-7 5-(3,5-dinitro-phenyl)-oxazole-4-carboxylic acid methyl ester 

Relevant articles and documents

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

Copper-Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3-Azaphospholes

A novel copper-catalyzed synthetic method is described for phosphorous- and nitrogen-containing heterocycles such as 1,3-azaphospholes. Cycloaddition reactions of various isocyanoacetates with phosphaalkynes in the presence of copper bromide, bis(diphenylphosphino)methane (dppm), and potassium carbonate afford the corresponding 1,3-azaphospholes in high yields with complete selectivity. Some dppm-bridged dicopper complexes were identified as active species for the formation of 1,3-azaphospholes.

Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides

This paper reports the tandem reaction strategy of the Passerini/Staudinger/aza-Wittig reaction based on the in situ capture of isocyanides. According to this strategy, isocyanides are synthesized in situ and immediately work as the substrate for the Passerini reaction and postmodification tandem reaction in one pot. In addition, two types of new compounds, 5-oxo-3,5-dihydrobenzo[e][1,4]oxazepines and 6-oxo-5,6-dihydro-2H-1,4-oxazines, were synthesized using the tandem reaction strategy that includes five-step transformations in one pot.