Ethyl isobutyrylacetate

Base Information

• Chemical Name: Ethyl isobutyrylacetate
• CAS No.: 7152-15-0
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 2918300090
• European Community (EC) Number: 230-491-9
• NSC Number: 62029
• UNII: M3WMK56MNB
• DSSTox Substance ID: DTXSID00221758
• Nikkaji Number: J56.056A
• Wikidata: Q72475584
• Mol file: 7152-15-0.mol

Synonyms:Ethyl isobutyrylacetate;7152-15-0;Ethyl 4-methyl-3-oxopentanoate;4-methyl-3-oxo-pentanoic acid ethyl ester;Pentanoic acid, 4-methyl-3-oxo-, ethyl ester;Ethyl isobutyroylacetate;M3WMK56MNB;Valeric acid, 4-methyl-3-oxo-, ethyl ester;EINECS 230-491-9;.gamma.,.gamma.-Dimethylacetoacetic acid ethyl ester;NSC-62029;AI3-37917;Ethyl alpha -isobutyroylacetate;Ethylisobutyrylacetate;ethyl isobutyryl acetate;ethyl iso-butyrylacetate;ethyl 2-isobutyrylacetate;UNII-M3WMK56MNB;ethyl 2-(isobutyryl)acetate;NCIOpen2_003819;ethyl 3-oxo-4-methylvalerate;Ethyl isobutyrylacetate, 95%;SCHEMBL182126;Ethyl 4-Methyl-3-oxovalerate;ethyl 4-methyl-3-oxo-valerate;ethyl 4-methyl-3-oxo-pentanoate;DTXSID00221758;Isobutyrylacetic Acid Ethyl Ester;Ethyl .alpha. -isobutyroylacetate;ethyl 3-isopropyl-3-oxopropanoate;3-Oxo-4-methylpentanoic acid ethyl;ethyl 3-isopropyl-3-oxo-propionate;NSC62029;MFCD00009198;NSC 62029;STL185655;AKOS005206743;CS-W016205;DS-1297;ETHYL-3-OXO-4-METHYLPENTANOATE;4-Methyl-3-oxovaleric Acid Ethyl Ester;3-keto-4-methyl valeric acid ethyl ester;4-methyl-3-oxopentanoic acid ethyl ester;E0882;FT-0600784;EN300-67503;O11797;3-OXO-4-METHYLPENTANOIC ACID ETHYL ESTER;Ethyl isobutyrylacetate, purum, >=95.0% (GC);PENTANOIC ACID,4-METHYL,3-OXO,ETHYL ESTER;beta-KETO-gamma-METHYLVALERIC ACID ETHYL ESTER;J-521260

Chemical Property of Ethyl isobutyrylacetate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 1.29mmHg at 25°C
• Melting Point: -9 °C(lit.)
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 173 °C at 760 mmHg
• PKA: 10.61±0.46(Predicted)
• Flash Point: 53.3 °C
• PSA: 43.37000
• Density: 0.979 g/cm³
• LogP: 1.16470
• Storage Temp.: Flammables area
• Solubility.: Soluble in chloroform and methanol.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl Isobutyrylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C(C)C
• Uses: Ethyl Isobutyrylacetate is used in the synthesis of piperazine derivatives as possible multireceptor atypical antipsychotics, affecting dopamine and serotonin receptor properties . Also used in the synthesis of pyrazinecarboxamide DGAT1 (diacylglycerol acyltransferase 1) inhibitors used in the treatment of obesity.

Technology Process of Ethyl isobutyrylacetate

There total 32 articles about Ethyl isobutyrylacetate 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: 99.0%

hydrogen ethyl malonate (1071-46-1) + isobutyryl chloride (79-30-1) → ethyl 4-methyl-3-oxo-pentanoate (7152-15-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

DOI:10.1002/hlca.19950780318

Reference yield: 91.0%

Ethyl (+/-)-3-hydroxy-4-methyl-4-pentenoate (122622-90-6) → ethyl 4-methyl-3-oxo-pentanoate (7152-15-0)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In water; acetone; at 60 ℃; for 16h; chemoselective reaction;

DOI:10.1002/chem.201603825

Reference yield: 83.0%

ethyl bromoacetate (105-36-2) + N-(methylpropionyl)oxazolidin-2-one (109853-52-3) → ethyl 4-methyl-3-oxo-pentanoate (7152-15-0)

Guidance literature:

With zinc; In tetrahydrofuran; 1) 30 deg C, 2 h, 2) reflux, 18 h;

DOI:10.1021/jo00055a046

upstream raw materials:

ethanol

isobutyrylacetic acid

4-methyl-3-oxopentanonitrile

ethyl 3-oxo-2-acetyl-4-methylpentanoate

Downstream raw materials:

(Z)-2-isobutyryl-3-phenylacrylic acid ethyl ester

5-methyl-4-oxo-2-phenyl-hexane-1,1,3-tricarboxylic acid triethyl ester

2,3-dihydro-6-isopropyl-2-thioxopyrimidin-4(1H)-one

3-isopropyl-2-cyclohexen-1-one

Refernces

• 1、 Cheng, Long,Liu, Xing-Hai,Wen, Yong-Hui,Wu, Ning-Jie,Xu, Tian-Ming. "Design, Synthesis, and Pesticidal Activities of Pyrimidin-4-amine Derivatives Bearing a 5-(Trifluoromethyl)-1,2,4-oxadiazole Moiety". . p. 6968 - 6980. Retrieved 2021/07/19.
• 2、 Vil', Vera A.,dos Passos Gomes, Gabriel,Bityukov, Oleg V.,Lyssenko, Konstantin A.,Nikishin, Gennady I.,Alabugin, Igor V.,Terent'ev, Alexander O.. "Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate". supporting information. p. 3372 - 3376. Retrieved 2018/02/28.