Methyl (2E)-5-bromopent-2-enoate

Base Information

• Chemical Name: Methyl (2E)-5-bromopent-2-enoate
• CAS No.: 67810-57-5
• Molecular Formula: C₆H₉BrO₂
• Molecular Weight: 193.04
• NSC Number: 268911
• DSSTox Substance ID: DTXSID80420929
• Nikkaji Number: J2.741.110J,J2.570.074K
• Mol file: 67810-57-5.mol

Synonyms:67810-57-5;methyl (E)-5-bromopent-2-enoate;METHYL (2E)-5-BROMOPENT-2-ENOATE;methyl 5-bromopent-2-enoate;NSC268911;SCHEMBL4451337;DTXSID80420929;5-Bromo-2-pentenoic acid methyl ester;NSC-268911;(E)-5-Bromo-2-pentenoic acid methyl ester;(E)-5-bromo-pent-2-enoic acid methyl ester

Chemical Property of Methyl (2E)-5-bromopent-2-enoate

Chemical Property:

• Vapor Pressure: 0.171mmHg at 25°C
• Boiling Point: 212.7°C at 760 mmHg
• Flash Point: 82.4°C
• PSA: 26.30000
• Density: 1.4g/cm³
• LogP: 1.50060
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 191.97859
• Heavy Atom Count: 9
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CCCBr
• Isomeric SMILES: COC(=O)/C=C/CCBr

Technology Process of Methyl (2E)-5-bromopent-2-enoate

There total 5 articles about Methyl (2E)-5-bromopent-2-enoate 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:

methyl (E)-5-mesyloxypentan-2-enoate (62592-76-1) → methyl (E)-5-bromo-2-pentenoate (123282-88-2,67810-57-5)

Guidance literature:

With lithium bromide; In diethyl ether;

DOI:10.1021/ja00503a033

Reference yield:

methyl trans-5-hydroxy-2-pentenoate (62592-80-7) → methyl (E)-5-bromo-2-pentenoate (123282-88-2,67810-57-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

2: LiBr / diethyl ether

With triethylamine; lithium bromide; In diethyl ether; dichloromethane;

DOI:10.1021/ja00503a033

Reference yield:

3-bromopropanal (65032-54-4) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (E)-5-bromo-2-pentenoate (123282-88-2,67810-57-5)

Guidance literature:

In toluene; at 21 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.04.069

upstream raw materials:

methyl (E)-5-mesyloxypentan-2-enoate

3-bromopropanal

methyl (triphenylphosphoranylidene)acetate

methyl trans-5-hydroxy-2-pentenoate

Refernces

• 1、 Bunce, Richard A.,Irwin, Derek A.. "A One-pot Synthesis of (E)-5-Bromo-2-pentenoate Esters". . p. 2979 - 2982. Retrieved 2007/10/02.