2,2-Dibromo-3-oxo-butyric acid ethyl ester

Base Information

• Chemical Name: 2,2-Dibromo-3-oxo-butyric acid ethyl ester
• CAS No.: 89415-67-8
• Molecular Formula: C6H8Br2O3
• Molecular Weight: 287.936
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID10459565
• Nikkaji Number: J1.584.267I
• Wikidata: Q82283366
• Mol file: 89415-67-8.mol

Synonyms:2,2-Dibromo-3-oxo-butyric acid ethyl ester;89415-67-8;ethyl 2,2-dibromo-3-oxobutanoate;Butanoic acid, 2,2-dibromo-3-oxo-, ethyl ester;ethyl 2,2-dibromo-acetoacetate;SCHEMBL6297048;DTXSID10459565;MFCD11845706;AKOS015838725;AS-5826;2,2-Dibromoacetoacetic acid ethyl ester;CS-0325989

Chemical Property of 2,2-Dibromo-3-oxo-butyric acid ethyl ester

Chemical Property:

• PSA: 43.37000
• LogP: 1.62460
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 287.88197
• Heavy Atom Count: 11
• Complexity: 177

Purity/Quality:

98%min ^*data from raw suppliers

2,2-Dibromo-3-oxobutyric acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)C)(Br)Br

Technology Process of 2,2-Dibromo-3-oxo-butyric acid ethyl ester

There total 8 articles about 2,2-Dibromo-3-oxo-butyric 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: 96.0%

ethyl acetoacetate (141-97-9) → ethyl 2,2-dibromoacetoacetate (89415-67-8)

Guidance literature:

With sodium hydroxide; bromine; In acetic acid; acetone; at 0 ℃;

DOI:10.1016/j.tetlet.2005.05.055

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:

ethyl acetoacetate

bromine

Dess-Martin periodane

Downstream raw materials:

diethyl 2,5-(dihydroxy)terephthalate

ethyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate

(E)-1-acetyl-1-(ethoxycarbonyl)-2-phenylcyclopropane

(Z)-1-acetyl-1-(ethoxycarbonyl)-2-phenylcyclopropane

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、 Cui, Xiao-Meng,Guan, Yong-Hong,Li, Na,Lv, Hao,Fu, Lin-An,Guo, Kun,Fan, Xiaohui. "A mild and efficient method for bromination of alcohols using α,α-dibromo-β-dicarbonyl compounds as halogen sources". supporting information. p. 90 - 93. Retrieved 2014/01/06.