2-Bromo-3-oxobutyric acid ethyl ester

Base Information

• Chemical Name: 2-Bromo-3-oxobutyric acid ethyl ester
• CAS No.: 609-13-2
• Molecular Formula: C₆H₉BrO₃
• Molecular Weight: 209.04
• Hs Code.: 2918300090
• Mol file: 609-13-2.mol

Synonyms:Ethyl 4-bromo-3-oxobutanoate;Butanoic acid, 4-bromo-3-oxo-, ethyl ester;4-Bromo-3-oxobutanoic acid ethyl ester;Ethyl 4-bromoacetoacetate;

Chemical Property of 2-Bromo-3-oxobutyric acid ethyl ester

Chemical Property:

• Refractive Index: 1.4630 (estimate)
• Boiling Point: 231.6 °C at 760 mmHg
• PKA: 8.14±0.46(Predicted)
• Flash Point: 93.9 °C
• PSA: 43.37000
• Density: 1.478 g/cm³
• LogP: 0.90200
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-oxo-butyricacidethylester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 2-Bromo-3-oxobutanoate is useful for preparing elagolix intermediate.

Technology Process of 2-Bromo-3-oxobutyric acid ethyl ester

There total 8 articles about 2-Bromo-3-oxobutyric acid ethyl ester 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: 85.0%

ethyl 2,2-dibromoacetoacetate (89415-67-8) → ethyl 2-bromoacetoacetate (84911-18-2,609-13-2) + ethyl acetoacetate (141-97-9)

Guidance literature:

With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate; at 125 ℃; for 0.0333333h; under 2585.74 Torr; microwave irradiation;

DOI:10.1016/j.tet.2006.10.035

Reference yield: 75.0%

ethyl acetoacetate (141-97-9) → ethyl 2-bromoacetoacetate (84911-18-2,609-13-2) + ethyl 2,2-dibromoacetoacetate (89415-67-8)

Guidance literature:

With Oxone; ammonium bromide; In methanol; at 20 ℃; for 3h; regioselective reaction;

DOI:10.1016/j.tetlet.2011.11.011

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl 2-bromoacetoacetate (84911-18-2,609-13-2) + 4-bromoethyl acetoacetate (13176-46-0) + ethyl 2,2-dibromoacetoacetate (89415-67-8)

Guidance literature:

With bromine; In acetic acid; at 20 ℃; for 0.0166667h;

DOI:10.1021/ol0271638

upstream raw materials:

chloroform

2-bromo-1,2,2-triphenyl-ethanone

ethyl acetoacetate

water

Downstream raw materials:

ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate

ethyl 2-methyl-6-nitroimidazo[1,2-a]pyridine-3-carboxylate

tetraethyl ethane-1,1,2,2-tetracarboxylate

diethyl malonate

Refernces

• 1、 Wong, Jonathan,Ke, Zhihai,Yeung, Ying-Yeung. "Lipophilic indole mediated chemoselective α-monobromination of 1,3-dicarbonyl compounds". . . Retrieved 2020/03/04.
• 2、 MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Marri, Mahender Reddy,Peraka, Swamy,Nama, Narender. "Oxidative bromination of ketones using ammonium bromide and oxone". supporting information; experimental part. p. 191 - 195. Retrieved 2012/01/17.