Methyl 4-oxo-2-butenoate

Base Information

• Chemical Name: Methyl 4-oxo-2-butenoate
• CAS No.: 5837-72-9
• Molecular Formula: C5H6O3
• Molecular Weight: 114.101
• European Community (EC) Number: 230-809-6,833-944-4
• Nikkaji Number: J1.540.044G,J212.322C
• Mol file: 5837-72-9.mol

Synonyms:5837-72-9;Fumaraldehydic Acid Methyl Ester;Methyl 4-oxobut-2-enoate;Methyl 4-oxo-2-butenoate;7327-99-3;3-(Methoxycarbonyl)-2-propenal;methyl (E)-4-oxobut-2-enoate;Methyl Fumaraldehydate;FUMARALDEHYDICACIDMETHYLESTER;2-Butenoic acid, 4-oxo-, methyl ester, (2E)-;EINECS 230-809-6;METHYL (2E)-4-OXOBUT-2-ENOATE;Fumaraldehydic acid, methyl ester;SCHEMBL2560582;SCHEMBL2560585;(e)-methyl 4-oxobut-2-enoate;3-(Methoxycarbonyl)acrylaldehyde;CRBJVPSOOMDSPT-NSCUHMNNSA-N;4-oxo-2-butenoic acid methyl ester;Methyl (2E)-4-oxo-2-butenoate #;MFCD00191651;AKOS016008845;(E)-4-Oxo-2-butenoic acid methyl ester;(E)-4-oxo-but-2-enoic acid methyl ester;F0351;EN300-182808;2-Butenoic acid, 4-oxo-, methyl ester, (E)-;EN300-6740406

Chemical Property of Methyl 4-oxo-2-butenoate

Chemical Property:

• Melting Point: 40 °C
• Boiling Point: 88 °C / 40mmHg
• Flash Point: 71.2oC
• PSA: 43.37000
• Density: 1.081±0.06 g/cm3(Predicted)
• LogP: -0.08550
• Storage Temp.: Refrigerator
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 114.031694049
• Heavy Atom Count: 8
• Complexity: 115

Purity/Quality:

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

3-(Methoxycarbonyl)-2-propenal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC=O
• Isomeric SMILES: COC(=O)/C=C/C=O

Technology Process of Methyl 4-oxo-2-butenoate

There total 15 articles about Methyl 4-oxo-2-butenoate 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: 98.0%

monofumaraldehyde dimethylacetal monomethylester (32815-00-2) → methyl (E)-4-oxo-2-butenoate (5837-72-9)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 1.5h; Heating;

DOI:10.1016/S0040-4020(02)00151-5

Reference yield: 90.0%

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → methyl (E)-4-oxo-2-butenoate (5837-72-9)

Guidance literature:

With ozone; In methanol; dichloromethane; at -30 ℃;

DOI:10.1016/j.tetlet.2006.06.066

Reference yield: 89.0%

methyl 4-hydroxy-2-butenoate (29576-13-4) → methyl (E)-4-oxo-2-butenoate (5837-72-9)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1271/bbb.63.1253

upstream raw materials:

crotonic acid methyl ester

sorbic acid methyl ester

(2E,4E)-methylhexa-2,4-dienoate

methyl crotonate

Downstream raw materials:

(E)-3-((S)-2-Phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-acrylic acid methyl ester

methyl (2E,4Z)-deca-2,4-dienoate

methyl (2E,4E)-decadienoate

(2E,5E)-(Ss)-methyl 4-hydroxy-5-(p-tolylsulfinyl)-2,5-tetradecadienoate

Refernces

• 1、 Hudlicky,Seoane,Lovelace. "Intramolecular [4 + 1] pyrroline annulation via azide-diene cycloadditions. 2. Formal stereoselective total syntheses of (±)-platynecine, (±)-hastanecine, (±)-turneforcidine, and (±)-dihydroxyheliotridane". . p. 2094 - 2099. Retrieved 1988.
• 2、 -. "NOVEL IDO INHIBITORS AND METHODS OF USE THEREOF". Page/Page column 24-28. . Retrieved 2008/12/07.
• 3、 Satoh, Tsuyoshi,Hanaki, Noriko,Kuramochi, Yuko,Inoue, Yujiro,Hosoya, Kayo,Sakai, Ken. "A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant". . p. 2533 - 2549. Retrieved 2007/10/03.