Methyl 5-bromo-4-oxopentanoate

Base Information

• Chemical Name: Methyl 5-bromo-4-oxopentanoate
• CAS No.: 53856-93-2
• Molecular Formula: C6H9BrO3
• Molecular Weight: 209.04
• European Community (EC) Number: 695-983-1
• DSSTox Substance ID: DTXSID10431841
• Nikkaji Number: J522.625B
• Wikidata: Q82245836
• Mol file: 53856-93-2.mol

Synonyms:methyl 5-bromo-4-oxopentanoate;53856-93-2;MFCD18800850;methyl 5-bromolevulinate;Methyl 5-bromo-4-oxo-pentanoate;5-bromolevulinic acid methyl ester;5-bromo-4-oxo-pentanoic acid methyl ester;5-bromolevulinic methyl ester;methyl5-bromo-4-oxopentanoate;SCHEMBL1160631;DTXSID10431841;AUQDWNOSVDUIAT-UHFFFAOYSA-N;AKOS005264425;5-bromo-4-oxo-valeric acid methylester;4-Oxo-5-bromopentanoic acid methyl ester;NS-02309;SY034031;CS-0042170;B-8916;D72688;EN300-114360;A904985

Chemical Property of Methyl 5-bromo-4-oxopentanoate

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 207.97351
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(=O)CBr

Technology Process of Methyl 5-bromo-4-oxopentanoate

There total 19 articles about Methyl 5-bromo-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: 90.0%

2-methoxycarbonylethyl (trimethylsilyl)methyl ketone (109988-02-5) → methyl 5-bromo-4-oxopentanoate (53856-93-2)

Guidance literature:

With bromine; In tetrachloromethane; 1.) -20 deg C, 2.) room temperature;

Reference yield: 83.0%

methanol (67-56-1) + levulinic acid (123-76-2) → methyl 5-bromo-4-oxopentanoate (53856-93-2)

Guidance literature:

With bromine; at 70 ℃; for 2.16667h;

DOI:10.1021/cc100041m

Reference yield: 82.0%

levulinic acid methyl ester (624-45-3) → methyl 5-bromo-4-oxopentanoate (53856-93-2)

Guidance literature:

With copper(ll) bromide; In methanol; chloroform; at 40 ℃; for 4h; Reagent/catalyst; Solvent; Time; Catalytic behavior; Green chemistry;

DOI:10.1039/c9ra01517e

upstream raw materials:

diazomethane

4-methoxy-butyryl chloride

methanol

levulinic acid

Downstream raw materials:

methyl 5-(1,3-dioxoisoindolin-2-yl)-4-oxopentanoate

2-<2-Oxo-4-methoxycarbonyl-butyl>-2-methoxycarbonyl-cyclohexanon

(S)-1-Benzyl-5-[4-methoxycarbonyl-2-oxo-but-(E)-ylidene]-pyrrolidine-2-carboxylic acid tert-butyl ester

(R)-1-Benzyl-5-[4-methoxycarbonyl-2-oxo-but-(E)-ylidene]-pyrrolidine-2-carboxylic acid tert-butyl ester

Refernces

• 1、 Ha,Lee,Ha,Park. "Selective bromination of ketones. A convenient synthesis of 5-aminolevulinic acid". . p. 2557 - 2562. Retrieved 1994.
• 2、 Mac Donald. "". . p. 3257. Retrieved 1974.
• 3、 -. "Preparation method 5 - ALA intermediate 5 - bromoolevulinic acid ester". Paragraph 0028-0030; 0039-0054. . Retrieved 2021/09/22.
• 4、 Nam, Gibeom,Jung, Jun Min,Park, Hyun-Ju,Baek, Seung Yeop,Baek, Ki Seon,Mok, Hui yeon,Kim, Da Eun,Jung, Young Hoon. "Structure-activity relationship study of thiazolyl-hydroxamate derivatives as selective histone deacetylase 6 inhibitors". . p. 3408 - 3420. Retrieved 2019/06/25.