Acetylacrylic Acid Methyl Ester

Base Information

• Chemical Name: Acetylacrylic Acid Methyl Ester
• CAS No.: 2833-24-1
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• European Community (EC) Number: 626-447-7
• DSSTox Substance ID: DTXSID401020437
• Nikkaji Number: J144.570G,J207.895C
• ChEMBL ID: CHEMBL4565546
• Mol file: 2833-24-1.mol

Synonyms:Acetylacrylic Acid Methyl Ester;2833-24-1;Methyl Acetylacrylate;Methyl trans-4-oxo-2-pentenoate;methyl (E)-4-oxopent-2-enoate;methyl (2E)-4-oxopent-2-enoate;4188-88-9;(E)-methyl 4-oxopent-2-enoate;ACETYLACRYLICACIDMETHYLESTER;2-Pentenoic acid, 4-oxo-, methyl ester, (2E)-;2-Pentenoic acid, 4-oxo-, methyl ester, (Z)-;Methyl 4-oxo-2-pentenoate;SCHEMBL1413207;SCHEMBL1413208;CHEMBL4565546;GLVNZYODMKSEPS-ONEGZZNKSA-;Methyl (E)-4-oxo-2-pentenoate;DTXSID401020437;Methyl (2Z)-4-oxo-2-pentenoate;MFCD00059331;AKOS015894026;(E)-3-Acetylacrylic acid methyl ester;A0071;EN300-134607;EN300-364931;M-4460;2-Pentenoic acid, 4-oxo-, methyl ester, (E)-;10.14272/GLVNZYODMKSEPS-ONEGZZNKSA-N.1;doi:10.14272/GLVNZYODMKSEPS-ONEGZZNKSA-N.1;Methyl trans-4-oxo-2-pentenoate, >=97.0% (GC);InChI=1/C6H8O3/c1-5(7)3-4-6(8)9-2/h3-4H,1-2H3/b4-3+

Chemical Property of Acetylacrylic Acid Methyl Ester

Chemical Property:

• Melting Point: 59-61 °C(lit.)
• PSA: 43.37000
• LogP: 0.30460
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 146

Purity/Quality:

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

Methyl trans-4-oxo-2-pentenoate ≥97.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 906914
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Acetylacrylic Acid Methyl Ester

There total 2 articles about Acetylacrylic Acid Methyl Ester 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:

methyl 5-bromo-4-oxopentanoate (53856-93-2) + 3-bromo-4-oxopentanoic acid methyl ester (95678-51-6) + potassium phtalimide (1074-82-4) → phthalimide (136918-14-4,85-41-6) + methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate (109258-71-1) + methyl (E)-4-oxo-2-pentenoate (2833-24-1)

Guidance literature:

In N,N-dimethyl-formamide; at 0 - 5 ℃; for 0.5 - 0.583333h;

Reference yield:

2-Bromo-4-oxo-pentanoic acid methyl ester → levulinic acid methyl ester (624-45-3) + methyl (E)-4-oxo-2-pentenoate (2833-24-1)

Guidance literature:

With triethylamine; In dichloromethane; Yield given. Yields of byproduct given; 1.) 15 min, -78 deg C; 2.) 105 min, room temp.;

Reference yield: 99.0%

methyl (E)-4-oxo-2-pentenoate (2833-24-1) + isoprene (78-79-5,9003-31-0) → C11H16O3

Guidance literature:

With aluminum tri-bromide; C₂₈H₁₇BF₁₅NO₂; In dichloromethane; ethylene dibromide; at -78 ℃; for 4h; Reagent/catalyst; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01692

upstream raw materials:

methyl 5-bromo-4-oxopentanoate

3-bromo-4-oxopentanoic acid methyl ester

potassium phtalimide

Downstream raw materials:

methyl 2-(1-methyl-2-oxocyclohexyl)-4-oxopentanoate

(1S,2R,3S)-3-Acetyl-5-oxo-cyclohexane-1,2-dicarboxylic acid dimethyl ester

(1R,2R,3S)-3-Acetyl-5-oxo-cyclohexane-1,2-dicarboxylic acid dimethyl ester

(1S,3S)-2-Acetyl-5-oxo-cyclohexane-1,3-dicarboxylic acid dimethyl ester