Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

Base Information

• Chemical Name: Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate
• CAS No.: 154325-75-4
• Molecular Formula: C₉H₁₅BrO₃
• Molecular Weight: 251.12
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID40399203
• Nikkaji Number: J2.689.131K
• Wikidata: Q72473184
• Mol file: 154325-75-4.mol

Synonyms:ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate;154325-75-4;Pentanoic acid,5-bromo-2,2-dimethyl-4-oxo-, ethyl ester;Pentanoic acid,5-broMo-2,2-diMethyl-4-oxo-,ethyl ester;5-Bromo-2,2-dimethyl-4-oxopentanoic Acid Ethyl Ester;SCHEMBL1253667;DTXSID40399203;Pentanoic acid, 5-broMo-2,2-diMethyl-4-oxo-, ethyl ester;LVXCDNNMZJAPOG-UHFFFAOYSA-N;AKOS016011462;CS-15641;CS-0006849;FT-0668176;FT-0697743;D72457;5-bromo-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester

Chemical Property of Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

Chemical Property:

• Appearance/Colour: Colourless Oil
• Vapor Pressure: 0.0021mmHg at 25°C
• Refractive Index: 1.469
• Boiling Point: 290.2 °C at 760 mmHg
• Flash Point: 129.3 °C
• PSA: 43.37000
• Density: 1.315 g/cm³
• LogP: 1.92980
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 250.02046
• Heavy Atom Count: 13
• Complexity: 199

Purity/Quality:

≥95% ^*data from raw suppliers

Ethyl5-Bromo-2,2-dimethyl-4-oxopentanoate+Ethyl5-Chloro-2,2-dimethyl-4-oxopentanoate(Bromo/ChloroMixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C)CC(=O)CBr
• Uses: Indolylalkanoate intermediate as leukotriene biosynthesis inhibitors Indolylalkanoate intermediate as leukotriene biosynthesis inhibitors.

Technology Process of Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

There total 2 articles about Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate 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%

ethyl 4-chloro-2,2-dimethyl-4-pentenoate (118427-36-4) → 5-bromo-2,2-dimethyl-4-oxopentanoic acid ethyl ester (154325-75-4)

Guidance literature:

With bromine; In ethanol; water; at -5 - 20 ℃; for 2h;

Reference yield:

Ethyl isobutyrate (97-62-1) → 5-bromo-2,2-dimethyl-4-oxopentanoic acid ethyl ester (154325-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.33 h / -78 - -65 °C

1.2: 18 h / 20 °C

2.1: bromine; water / ethanol / 2 h / -5 - 20 °C

With water; bromine; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

Reference yield: 98.0%

5-bromo-2,2-dimethyl-4-oxopentanoic acid ethyl ester (154325-75-4) + 2-methylpropan-2-thiol (75-66-1) → ethyl 5-t-butylthio-2,2-dimethyl-4-oxo-pentanoate (136558-13-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

upstream raw materials:

ethyl 4-chloro-2,2-dimethyl-4-pentenoate

Ethyl isobutyrate

Downstream raw materials:

ethyl 5-t-butylthio-2,2-dimethyl-4-oxo-pentanoate

Refernces

• 1、 -. "DIHYDROPYRIMIDINE DERIVATIVES AND USES THEREOF IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES". Page/Page column 39; 62-64. . Retrieved 2020/01/24.
• 2、 -. "A hedgehog pathway inhibitor and its preparation method and application". Paragraph 0041; 0042; 0045. . Retrieved 2019/04/10.