Methyl acetoacetate

Base Information

• Chemical Name: Methyl acetoacetate
• CAS No.: 105-45-3
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 29183000
• European Community (EC) Number: 203-299-8
• ICSC Number: 1086
• UN Number: 1993
• UNII: CW4I82QAX1
• DSSTox Substance ID: DTXSID9026716
• Nikkaji Number: J45.957G
• Wikidata: Q424860
• Metabolomics Workbench ID: 37198
• ChEMBL ID: CHEMBL3186053
• Mol file: 105-45-3.mol

Synonyms:acetoacetic acid methyl ester;methyl 3-oxobutanoate;methyl acetoacetate

Chemical Property of Methyl acetoacetate

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Vapor Pressure: 1.54mmHg at 25°C
• Melting Point: -80 °C
• Refractive Index: n20/D 1.419(lit.)
• Boiling Point: 169.4 °C at 760 mmHg
• PKA: 10.67±0.46(Predicted)
• Flash Point: 61.6 °C
• PSA: 43.37000
• Density: 1.039 g/cm³
• LogP: 0.13850
• Storage Temp.: 2-8°C
• Solubility.: 460 g/L (20°C)
• Water Solubility.: 460 g/L (20 ºC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106
• Transport DOT Label: Combustible Liquid

Purity/Quality:

98% ^*data from raw suppliers

Methyl acetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Esters (
• Canonical SMILES: CC(=O)CC(=O)OC
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. Exposure could cause lowering of consciousness.
• Uses: Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives. 3-Oxobutanoic Acid Methyl Ester is a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones. Methyl acetoacetate is used as a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.Methyl acetoacetate (MAA) is used for the synthesis of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.

Technology Process of Methyl acetoacetate

There total 68 articles about Methyl acetoacetate 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: 90.0%

methanol (67-56-1) + tert-butyl acetoacetate (1694-31-1) → acetoacetic acid methyl ester (105-45-3)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; for 12h; Heating;

DOI:10.1002/1521-3773(20011001)40:19<3672::AID-ANIE3672>3.0.CO;2-Y

Reference yield: 88.0%

-essigsaeure-methylester (109514-04-7) → acetic acid methyl ester (79-20-9) + acetic acid-(1-methoxy-vinyl ester) (13253-76-4) + tripropyltin chloride (2279-76-7) + acetoacetic acid methyl ester (105-45-3)

Guidance literature:

With acetyl chloride;

Reference yield: 87.3%

methanol (67-56-1) + citric acid (77-92-9,906507-37-7) → 3-oxopentanedioic acid dimethyl ester (1830-54-2) + dimethyl 2-methoxypropene-1,3-dicarboxylate (100009-70-9) + trimethyl aconitate (20820-77-3) + trimethyl citrate (1587-20-8) + acetoacetic acid methyl ester (105-45-3)

Guidance literature:

citric acid; With chlorosulfonic acid; In dichloromethane; at 10 - 15 ℃; for 5 - 6h;

methanol; In dichloromethane; at 3 - 35 ℃; for 2h; Conversion of starting material;

upstream raw materials:

4-methyleneoxetan-2-one

methanol

ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate

sodium methylate

Downstream raw materials:

methyl 6,11-dioxo-6,11- dihydrobenzo[f]pyrido [1,2-a]indole-12-carboxylate

3-methylaminobut-2-enoic acid methyl ester

dimethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate

methyl 2-benzylidene-3-oxobutanoate

Refernces

• 1、 Tezuka et al.. "-". . p. 443. Retrieved 1969.
• 2、 Jarowicki, Krzysztof,Kwitakowski, Stefan. "Catalytic Dimerization of Ketene. A Simple and Convenient Method for the Preparation of Diketene and Esters of Acetoacetic Acid". . p. 141 - 144. Retrieved 1985.
• 3、 Lapidus,Eliseev,Bondarenko,Sizan,Ostapenko,Beletskaya. "Synthesis of β-keto esters by carbonylation of halomethylketones". . p. 317 - 319. Retrieved 2002.
• 4、 Ensari, Yunus,Dhoke, Gaurao V.,Davari, Mehdi D.,Bocola, Marco,Ruff, Anna Jo?lle,Schwaneberg, Ulrich. "Inversion of cpADH5 Enantiopreference and Altered Chain Length Specificity for Methyl 3-Hydroxyalkanoates". . p. 12636 - 12645. Retrieved 2017.
• 5、 Ogibin,Yu.N.,Nikishin,G.I.. "-". . . Retrieved 1965.
• 6、 Kuznetsova,Zudin,Kuznetsova,Zaikovskii,Kajitani,Utsunomiya,Takahashi. "Versatile PdTe/C catalyst for liquid-phase oxidations of 1,3-butadiene". . p. 30 - 38. Retrieved 2016.
• 7、 Sidhom, Peter A.,El-Bastawissy, Eman,Salama, Abeer A.,El-Moselhy, Tarek F.. "Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents". supporting information. . Retrieved 2021/06/21.
• 8、 -. "Method for synthesizing methyl acetoacetate". Paragraph 0014-0031. . Retrieved 2020/08/09.