Methyl 4-oxobutanoate

Base Information

• Chemical Name: Methyl 4-oxobutanoate
• CAS No.: 13865-19-5
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2918300090
• European Community (EC) Number: 237-611-9
• DSSTox Substance ID: DTXSID20160736
• Nikkaji Number: J280.346A
• Wikidata: Q72494151
• Mol file: 13865-19-5.mol

Synonyms:Methyl 4-oxobutanoate;13865-19-5;4-OXOBUTANOIC ACID METHYL ESTER;Methyl 4-oxobutyrate;4-oxo-butyric acid methyl ester;methyl-4-oxobutanoate;MFCD00082185;Butanoic acid, 4-oxo-, methyl ester;4-oxobutyric acid methyl ester;EINECS 237-611-9;Methyl4-oxobutanoate;methyl 3-formylpropionate;3-carbomethoxypropionaldehyde;Methyl 4-oxobutanoate, 90%;SCHEMBL242764;DTXSID20160736;Succinaldehydic acid, methyl ester;BCP26085;3-formyl-propionic acid methyl ester;AKOS005137977;AS-37953;BP-27934;SY026183;AM20080287;FT-0600290;A22062;EN300-187997;J-007163;2,3,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonylchloride

Chemical Property of Methyl 4-oxobutanoate

Chemical Property:

• Appearance/Colour: Reddish brown viscous liquid
• Vapor Pressure: 1.71mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 167.3 °C at 760 mmHg
• Flash Point: 60.3 °C
• PSA: 43.37000
• Density: 1.037 g/cm³
• LogP: 0.13850
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 87.7

Purity/Quality:

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

Methyl4-oxobutanoate(~85%) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CCC=O
• Description: Methyl-4-oxobutyrate is a kind of oxobutyrate derivative. It is an important industrial intermediate. It, together with its methanol addition products such as methyl 4,4-dimethoxybutyrate and gamma- methoxy-gamma-butyrolactone are useful intermediates during the preparation of some important industrial compounds such as gamma- butyrolactone, 1,4-butanediol and glutamate. It is also useful as a model substrate during exploring the asymmetric henry reaction since it can assemble a stereodefined lactam with high efficiency and enantiomeric purity.
• Uses: Methyl 4-oxobutanoate may be used as a starting material to synthesize (-)-deoxoprosophylline, a piperidine alkaloid with therapeutic potential.

Technology Process of Methyl 4-oxobutanoate

There total 43 articles about Methyl 4-oxobutanoate 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: 100.0%

methyl 4-hydroxybutanoate (925-57-5) → 4-oxobutanoic acid methyl ester (13865-19-5)

Guidance literature:

methyl 4-hydroxybutanoate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.9b04142 DOI:10.1021/jacs.9b04142

Reference yield: 100.0%

methyl 4,4-dimethoxybutanoate (4220-66-0) → 4-oxobutanoic acid methyl ester (13865-19-5)

Guidance literature:

With acetic acid; In methanol; water; at 70 ℃; for 0.5h;

DOI:10.1246/cl.1982.23

Reference yield: 94.0%

succinic acid monomethylester chloride (1490-25-1) → 4-oxobutanoic acid methyl ester (13865-19-5)

Guidance literature:

With 2,6-dimethylpyridine; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; Inert atmosphere;

DOI:10.1002/chem.201504520

upstream raw materials:

2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester

succinic acid monomethylester chloride

diazomethane

Succinic semialdehyde

Downstream raw materials:

(E)-methyl 6-oxo-6-phenylhex-4-enoate

trans-(1S,3R)-(-)-2-benzyl-3-ethoxycarbonyl-7-methoxy-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

(5-methoxy-1H-indol-3-yl)acetic acid methyl ester

Refernces

• 1、 Komnatnyy, Vitaly V.,Taveras, Kennedy M.,Nandurkar, Nitin S.,Le Quement, Sebastian T.,Givskov, Michael,Nielsen, Thomas E.. "Synthesis of substituted γ- and δ-lactams through Mannich-type reactions of solid-supported N-acyliminium ions". . p. 3524 - 3530. Retrieved 2015.
• 2、 Adam, Waldemar,Makosza, Mieczyslaw,Saha-M?ller, Chantu R.,Zhao, Cong-Gui. "A mild and efficient Nef reaction for the conversion of nitro to carbonyl group by dimethyldioxirane (DMD) oxidation of nitronate anions". . p. 1335 - 1336. Retrieved 1998.
• 3、 Hershberg,Cason. "-". . p. 627,629 Anm. 2. Retrieved 1955.
• 4、 Taylor, Wesley G.. "Synthesis of 5,5-Dichloro-4-pentenoic Acid by the Wittig Reaction with Bromotrichloromethane and Triphenylphosphine". . p. 4290 - 4292. Retrieved 1981.
• 5、 Schellenberger,Heinroth,Huebner. "On the theory of thiamine pyrophosphate action. VI. Importance of the conformation situation between pyrimidine- and thiazole ring for the coenzyme effect of thiamine pyrophosphate in yeast pyruvate decarboxylase". . p. 506 - 511. Retrieved 1967.
• 6、 Bultel-Poncé, Valérie,Degrange, Thomas,Durand, Thierry,Galano, Jean-Marie,Guy, Alexandre,Merad, Jérémy,Oger, Camille,Reversat, Guillaume. "Total Synthesis of DHA and DPA n-3Non-Enzymatic Oxylipins". . . Retrieved 2021/12/02.
• 7、 Ogawa, Narihito,Amano, Takahito,Kobayashi, Yuichi. "Synthesis of Optically Active Maresin 2 and Maresin 2 n-3 DPA". supporting information. p. 295 - 298. Retrieved 2020/11/18.