Methyl 4-bromo-3-oxobutanoate

Base Information

• Chemical Name: Methyl 4-bromo-3-oxobutanoate
• CAS No.: 17790-81-7
• Molecular Formula: C5H7 Br O3
• Molecular Weight: 195.013
• Hs Code.: 2918300090
• NSC Number: 165240
• DSSTox Substance ID: DTXSID00304277
• Nikkaji Number: J873.414C
• Wikidata: Q82050102
• Mol file: 17790-81-7.mol

Synonyms:Methyl 4-bromo-3-oxobutanoate;17790-81-7;methyl 4-bromo-3-oxo-butanoate;Methyl 4-bromo-3-oxobutyrate;Butanoic acid, 4-bromo-3-oxo-, methyl ester;methyl 4-bromoacetoacetate;NSC165240;methyl-4-bromoacetoacetate;methyl4-bromo-3-oxo-butanoate;SCHEMBL2764239;DTXSID00304277;Methyl 4-bromo-3-oxobutanoate #;MFCD14635860;AKOS040768076;NSC-165240;s11869;4-Bromo-3-oxobutyric acid, methyl ester;SY310840

Chemical Property of Methyl 4-bromo-3-oxobutanoate

Chemical Property:

• Vapor Pressure: 0.164mmHg at 25°C
• Boiling Point: 213.4°Cat760mmHg
• PKA: 9.53±0.46(Predicted)
• Flash Point: 82.9°C
• PSA: 43.37000
• Density: 1.561g/cm³
• LogP: 0.51350
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 193.95786
• Heavy Atom Count: 9
• Complexity: 121

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(=O)CBr

Technology Process of Methyl 4-bromo-3-oxobutanoate

There total 9 articles about Methyl 4-bromo-3-oxobutanoate 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: 96.3%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + methanol (67-56-1) → methyl 4-bromo-3-oxobutanoate (17790-81-7)

Guidance literature:

With bromine; In ethyl acetate;

Reference yield: 82.0%

methanol (67-56-1) + 4-bromoethyl acetoacetate (13176-46-0) → methyl 4-bromo-3-oxobutanoate (17790-81-7)

Guidance literature:

With chloro-trimethyl-silane; at 20 ℃; for 24h;

DOI:10.1007/BF00961389

Reference yield: 78.36%

methanol (67-56-1) + 4-bromo-3-oxobutyric acid bromide (52148-44-4) → methyl 4-bromo-3-oxobutanoate (17790-81-7)

Guidance literature:

With pyridine; at -5 ℃; for 2h;

upstream raw materials:

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

acetoacetic acid methyl ester

methanol

4-bromoethyl acetoacetate

Downstream raw materials:

methyl 4-(diphenylphosphinoyl)-3-oxobutanoate

4-methoxyacetoacetic acid methylester

methyl γ-(2-cyclohexenyloxy)acetoacetate

methyl γ-ethoxyacetoacetate

Refernces

• 1、 Chan,T.H.,Brownbridge,P.. "-". . p. 578 - 579. Retrieved 1979.
• 2、 -. "Method for synthesizing cefcapene pivoxil side chain acid intermediate methyl 4-bromoacetoacetate through micro-reaction". Paragraph 0117-0020. . Retrieved 2019/08/30.
• 3、 Zou, Yunfan,Daane, Kent M.,Bentley, Walt J.,Millar, Jocelyn G.. "Synthesis and bioassay of racemic and chiral trans -α-Necrodyl Isobutyrate, the sex pheromone of the grape mealybug pseudococcus maritimus". experimental part. p. 4977 - 4982. Retrieved 2011/07/31.