Methyl 2-bromo-2-butenoate

Base Information

• Chemical Name: Methyl 2-bromo-2-butenoate
• CAS No.: 17642-18-1
• Molecular Formula: C5H7 Br O2
• Molecular Weight: 179.013
• Hs Code.: 2916190090
• European Community (EC) Number: 241-627-1
• Nikkaji Number: J287.100I,J661.437J
• Mol file: 17642-18-1.mol

Synonyms:Methyl 2-bromo-2-butenoate;17642-18-1;methyl 2-bromobut-2-enoate;Methyl 2-bromocrotonate;methyl (Z)-2-bromobut-2-enoate;(Z)-METHYL 2-BROMOBUT-2-ENOATE;EINECS 241-627-1;methyl bromo-crotonate;22966-48-9;Methyl-2-bromo-buten-2-oate;DMKWWKUPZZAUQL-ARJAWSKDSA-N;MFCD00042891;2-Bromo-2-butenoic acid methyl ester;2-BROMOCROTONIC ACID METHYL ESTER;AS-39089;CS-0188187;EN300-113965;J-011191;Methyl 2-bromo-2-butenoate, (cis+trans), >=95.0% (GC)

Chemical Property of Methyl 2-bromo-2-butenoate

Chemical Property:

• Vapor Pressure: 1.84mmHg at 25°C
• Refractive Index: n20/D 1.486
• Boiling Point: 165.8°Cat760mmHg
• Flash Point: 54.1°C
• PSA: 26.30000
• Density: 1.477g/cm³
• LogP: 1.45810
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 177.96294
• Heavy Atom Count: 8
• Complexity: 118

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-bromo-2-butenoate (cis+trans), ≥95.0% (GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=C(C(=O)OC)Br
• Isomeric SMILES: C/C=C(/C(=O)OC)\Br

Technology Process of Methyl 2-bromo-2-butenoate

There total 28 articles about Methyl 2-bromo-2-butenoate 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: 64.0%

acetaldehyde (75-07-0,9002-91-9) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl bromo-crotonate (17642-18-1,36297-23-1,22966-48-9)

Guidance literature:

methyl (triphenylphosphoranylidene)acetate; With N-Bromosuccinimide; In dichloromethane; at -20 - 20 ℃; Inert atmosphere;

acetaldehyde; With potassium carbonate; In dichloromethane; for 16h; Inert atmosphere;

DOI:10.1021/jacs.6b01941

Reference yield: 45.0%

crotonic acid methyl ester (623-43-8) → methyl bromo-crotonate (17642-18-1,36297-23-1,22966-48-9) + (E)-α-bromocrotonate de methyle (17642-18-1,22966-48-9,36297-23-1)

Guidance literature:

crotonic acid methyl ester; With bromine; In n-heptane; at 20 ℃; for 1h; Inert atmosphere;

With potassium carbonate; In n-heptane; acetonitrile; at 60 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/op200086t

Reference yield: 45.0%

crotonic acid methyl ester (623-43-8) → methyl bromo-crotonate (17642-18-1,36297-23-1,22966-48-9) + (E)-α-bromocrotonate de methyle (17642-18-1,22966-48-9,36297-23-1)

Guidance literature:

crotonic acid methyl ester; With bromine; In n-heptane; at 20 ℃; for 1h; Inert atmosphere;

With potassium carbonate; In n-heptane; acetonitrile; at 60 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/op200086t

upstream raw materials:

methyl crotonate

methyl 2,3-dibromobutyrate

diazomethane

(Z)-2-bromobut-2-enoic acid

Downstream raw materials:

(E)-α-bromocrotonate de methyle

cis bromo-1 methoxymethyl-2 dicarbomethoxy-1,2 cyclopropane

methyl bromo-crotonate

methyl (E)-5-<(tert-butyldiphenylsilyl)oxy>-2-<(E)-ethylidene>-4-methylpent-3-enoate

Refernces

• 1、 Fu, Liangbing,Guptill, David M.,Davies, Huw M. L.. "Rhodium(II)-catalyzed c-h functionalization of electron-deficient methyl groups". . p. 5761 - 5764. Retrieved 2016.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF S-BEFLUBUTAMID USING ASYMMETRIC HYDROGENATION". Page/Page column 27-28. . Retrieved 2021/08/20.