Methyl 2-acetamidoacrylate

Base Information

• Chemical Name: Methyl 2-acetamidoacrylate
• CAS No.: 35356-70-8
• Molecular Formula: C6H9 N O3
• Molecular Weight: 143.142
• Hs Code.: 29241990
• European Community (EC) Number: 609-121-9
• NSC Number: 156878
• UNII: GT3ARJ50FG
• DSSTox Substance ID: DTXSID70188849
• Nikkaji Number: J308.269E
• Wikipedia: Methyl_2-acetamidoacrylate
• Wikidata: Q65045796
• ChEMBL ID: CHEMBL4868054
• Mol file: 35356-70-8.mol

Synonyms:methyl 2-acetamidoacrylate;methyl-2-acetamidoacrylate;N-acetyldehydroalanine methyl ester

Chemical Property of Methyl 2-acetamidoacrylate

Chemical Property:

• Vapor Pressure: 0.000618mmHg at 25°C
• Melting Point: 50-52 ºC
• Refractive Index: 1.4340 (estimate)
• Boiling Point: 104 ºC (8 mmHg)
• Flash Point: >110 ºC
• PSA: 55.40000
• Density: 1.085 g/cm³
• LogP: 0.20010
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 174

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 2-acetamidoacrylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(=C)C(=O)OC
• Uses: Methyl 2-acetamidoacrylate exhibits anti-inflammatory property and decreases induced acute kidney injury in mice.

Technology Process of Methyl 2-acetamidoacrylate

There total 7 articles about Methyl 2-acetamidoacrylate 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: 68.0%

Ac-Cys-OMe (7652-46-2) → Methyl 2-acetamidoacrylate (35356-70-8)

Guidance literature:

With 1,4-Diiodobutane; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/acs.orglett.9b01013

Reference yield:

(μ3-MeC)CoRuWCp(CO)7(C(Me)(COOMe)NHC(Me)O) (108036-67-5) → dodecacarbonyl-triangulo-triruthenium (15243-33-1) + MeCCo2WCp(CO)8 + Methyl 2-acetamidoacrylate (35356-70-8)

Guidance literature:

With hydrogen; In benzene; autoclave, under H2 (30 bar), 5h, 60°C, filtration; detected by NMR and IR;

Reference yield:

(μ3-MeC)CoRuWCp(CO)7(C(Me)(COOMe)NHC(Me)O) (108036-67-5) → dodecacarbonyl-triangulo-triruthenium (15243-33-1) + (μ-3MeC)CoRuWCp(CO)8H (104780-08-7) + MeCCo2WCp(CO)8 + Methyl 2-acetamidoacrylate (35356-70-8)

Guidance literature:

With carbon monoxide; hydrogen; In benzene; autoclave, under CO (2 bar) and H2 (20 bar), 4h, 60°C, filtration; detected by NMR and IR;

upstream raw materials:

Ac-Cys-OMe

(S)-Propylene oxide

(μ3-MeC)CoRuWCp(CO)7(C(Me)(COOMe)NHC(Me)O)

Co(CO)3Ru(C(CH₃)(COOCH₃)NHC(O)CH₃)(CO)2Mo(C₅H₅)(CO)2CC₆H₅

Downstream raw materials:

N-Acetylcycloserin

pyruvic acid methyl ester

N-Acetamidoacrylic acid

(Z)-β-Chloro-N-acetyldehydroalanine methyl ester

Refernces

• 1、 Klimánková, Iveta,Hubálek, Martin,Matou?ek, Václav,Beier, Petr. "Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols". supporting information. p. 10097 - 10102. Retrieved 2019/12/23.
• 2、 Mani, Darjusch,Schacht, Hans-Thomas,Powell, Anne K.,Vahrenkamp, Heinrich. "Reversible and Diastereospecific Insertion of 2-Acetamidoacrylic Methyl Ester into the Metal-Hydrogen Function of Chiral Clusters". . p. 2245 - 2252. Retrieved 2007/10/02.