Ethyl 3-oxohexanoate

Base Information

• Chemical Name: Ethyl 3-oxohexanoate
• CAS No.: 3249-68-1
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 29183000
• European Community (EC) Number: 221-835-9
• NSC Number: 42868
• UNII: 8Q1AHG710E
• DSSTox Substance ID: DTXSID00186217
• Nikkaji Number: J100.919B
• Wikidata: Q27102838
• Metabolomics Workbench ID: 44807
• Mol file: 3249-68-1.mol

Synonyms:Ethyl 3-oxohexanoate;Ethyl butyrylacetate;3249-68-1;Ethyl butyroacetate;Hexanoic acid, 3-oxo-, ethyl ester;Ethyl 3-Ketohexanoate;Ethyl beta-ketohexanoate;ethylbutyrylacetate;Ethyl alpha-butyrylacetate;Ethyl .alpha.-butyrylacetate;FEMA No. 3683;3-Oxohexanoic Acid Ethyl Ester;3-Ketohexanoic Acid Ethyl Ester;ETHYL-3-OXOHEXANOATE;3-oxo-hexanoic acid ethyl ester;EINECS 221-835-9;UNII-8Q1AHG710E;AI3-23360;8Q1AHG710E;3-Keto-n-hexanoic acid ethyl ester;NSC-42868;ethyl butrylacetate;ethyl 3-oxo-caproate;Ethyl 3-oxo-hexanoate;ethyl 3-keto-n-hexanoate;Ethyl alpha -butyrylacetate;ETHYL BUTYROYLACETATE;SCHEMBL21832;Ethyl 3-oxohexanoate, 98%;Butyrylacetic acid ethyl ester;3-oxo-hexanoic-acid ethyl ester;Ethyl 3-oxohexanoate, >=98%;CHEBI:18119;FEMA 3683;KQWWVLVLVYYYDT-UHFFFAOYSA-;DTXSID00186217;NSC42868;STR02918;ETHYL 3-OXOHEXANOATE [FHFI];BBL027758;MFCD00009401;NSC 42868;STL185596;AKOS000121353;CS-W016203;ETHYL 3-PROPYL-3-OXOPROPANOATE;HY-W015487;ethyl butyrylacetate;ethyl 3-oxohexanoate;BP-12706;Ethyl butyrylacetate Ethyl 3-oxohexanoate;LS-75355;FT-0616296;K0030;EN300-21228;C02975;E76474;CAPROIC ACID, .BETA.-OXO-, ETHYL ESTER;J-018761;Q27102838;F0001-0965

Chemical Property of Ethyl 3-oxohexanoate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.243mmHg at 25°C
• Melting Point: -44°C
• Refractive Index: n20/D 1.427(lit.)
• Boiling Point: 206 °C at 760 mmHg
• PKA: 10.69±0.46(Predicted)
• Flash Point: 78.3 °C
• PSA: 43.37000
• Density: 0.981 g/cm³
• LogP: 1.30880
• Storage Temp.: Store below +30°C.
• Water Solubility.: IMMISCIBLE
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Butyrylacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC(=O)CC(=O)OCC
• Uses: Ethyl Butyrylacetate is used in the synthesis of pharmaceutical agents such as the anti-HIV agent (+/-)-Calanolide A.Also used in the synthesis of potent and selective polymerase inhibitors.

Technology Process of Ethyl 3-oxohexanoate

There total 47 articles about Ethyl 3-oxohexanoate 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: 94.0%

diazoacetic acid ethyl ester (623-73-4) + butyraldehyde (123-72-8) → ethyl butyroyl acetate (3249-68-1)

Guidance literature:

With zeolite Hβ; In 1,2-dichloro-ethane; for 8h; Heating;

DOI:10.1016/S0040-4020(98)00804-7

Reference yield: 87.0%

ethyl potassium malonate (6148-64-7) + butyric acid (107-92-6) → ethyl butyroyl acetate (3249-68-1)

Guidance literature:

butyric acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;

ethyl potassium malonate; With magnesium chloride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/cmdc.201800720

Reference yield: 85.0%

ethyl bromide (74-96-4) + ethyl acetoacetate (141-97-9) → ethyl butyroyl acetate (3249-68-1)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; hexane; mineral oil; at 0 ℃; for 0.166667h; Inert atmosphere;

ethyl bromide; In tetrahydrofuran; hexane; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

upstream raw materials:

ethyl bromide

ethyl 3-oxo-2-acetylhexanoate

sodium ethanolate

ethanol

Downstream raw materials:

4-(5-oxo-3-propyl-2,5-dihydro-pyrazol-1-yl)-benzoic acid

ethyl 3-aminocaproate

(8-ethyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid

Undecandion-(4,8)

Refernces

• 1、 Cooke Jr.,Jaw. "Charge-directed conjugate addition reactions of salts of unsaturated β-keto-esters". . p. 2213 - 2218. Retrieved 1992.
• 2、 Brown,E. et al.. "-". . p. 455 - 461. Retrieved 1973.
• 3、 Xu, Kai,Zheng, Yan,Ye, Yong,Liu, Delong,Zhang, Wanbin. "Desymmetrization of meso-dicarbonatecyclohexene with β-Hydrazino carboxylic esters via a Pd-catalyzed allylic substitution cascade". supporting information. p. 8836 - 8841. Retrieved 2020/11/30.
• 4、 Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin. "General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides". supporting information. p. 5679 - 5684. Retrieved 2019/08/01.