Methyl 2-(methylideneamino)acetate

Base Information

• Chemical Name: Methyl 2-(methylideneamino)acetate
• CAS No.: 39687-95-1
• Molecular Formula: C4H5NO2
• Molecular Weight: 99.0892
• Hs Code.: 29291090
• DSSTox Substance ID: DTXSID40960295
• Nikkaji Number: J3.296.496F
• Wikidata: Q72492174
• Mol file: 39687-95-1.mol

Synonyms:methyl 2-(methylideneamino)acetate;Methyl N-methylideneglycinate;SCHEMBL255150;N-Methyleneglycine methyl ester;DTXSID40960295

Chemical Property of Methyl 2-(methylideneamino)acetate

Chemical Property:

• Appearance/Colour: Clear yellow to brown liquid
• Vapor Pressure: 11.4mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Boiling Point: 75-76 °C10 mm Hg(lit.)
• Flash Point: 193 °F
• PSA: 26.30000
• Density: 1.09 g/mL at 25 °C(lit.)
• LogP: -0.69060
• Storage Temp.: −20°C
• Water Solubility.: Miscible with organic solvents. Slightly miscible with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 79.8

Purity/Quality:

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

Methyl isocyanoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CN=C
• Uses: Methyl isocyanoacetate is used in the copper-catalyzed, diastereoselective synthesis of oxazolines. It is involved in the direct aldol reaction with carbonyl compounds to prepare corresponding oxazoline by using catechol-copper network catalyst. Further, it is also involved in four-component Ugi condensation reaction. It undergoes asymmetric aldol reaction with fluorinated benzaldehyde using gold(I) as a catalyst. Methyl isocyanoacetate has been used in the copper-catalyzed, diastereoselective synthesis of oxazolines.

Technology Process of Methyl 2-(methylideneamino)acetate

There total 5 articles about Methyl 2-(methylideneamino)acetate 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: 75.0%

methyl N-formylglycinate (3154-54-9) → isocyanoacetic acid methyl ester (39687-95-1)

Guidance literature:

With diisopropylamine; trichlorophosphate; In dichloromethane;

DOI:10.1055/s-1985-31216

Reference yield: 72.0%

methyl 3-oxopropionate (63857-17-0) → isocyanoacetic acid methyl ester (39687-95-1)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/ja9612817

Reference yield:

methyl (E)-2-((1-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-2-hydroxy-3,3-dimethylbutylidene)amino)acetate → isocyanoacetic acid methyl ester (39687-95-1) + pivalaldehyde (630-19-3)

Guidance literature:

In ⁽²⁾H₈-toluene; at 200 ℃; for 0.166667h; Microwave irradiation; Sealed tube;

DOI:10.1021/acs.orglett.8b01561

upstream raw materials:

methyl N-formylglycinate

methyl 3-oxopropionate

potassium 2-isocyanoacetate

Downstream raw materials:

5-(2-methoxycarbonyl-4-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester

5-(2-methoxycarbonyl-5-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester

5-(2-methoxycarbonyl-6-nitro-phenyl)-oxazole-4-carboxylic acid methyl ester

dimethyl oxazole-4,5-dicarboxylate

Refernces

• 1、 ünver, M. Yagiz,Camacho, Carlos Jamie,D?mling, Alexander,Haupenthal, J?rg,Heine, Andreas,Hirsch, Anna K. H.,Jumde, Varsha R.,Klebe, Gerhard,Konstantinidou, Markella,Magari, Francesca,Sutanto, Fandi. "Rapid Discovery of Aspartyl Protease Inhibitors Using an Anchoring Approach". supporting information. . Retrieved 2020/04/10.
• 2、 Liu, Na,Chao, Fei,Liu, Ming-Guo,Huang, Nian-Yu,Zou, Kun,Wang, Long. "Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides". . p. 2366 - 2371. Retrieved 2019/05/16.