2-Hexenoic acid, methyl ester

Base Information

• Chemical Name: 2-Hexenoic acid, methyl ester
• CAS No.: 2396-77-2
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Hs Code.: 2916199590
• European Community (EC) Number: 607-296-6,925-056-1
• DSSTox Substance ID: DTXSID2062375
• Wikidata: Q72491174
• Mol file: 2396-77-2.mol

Synonyms:methyl hex-2-enoate;2-Hexenoic acid, methyl ester;2396-77-2;UNII-Q6M9281R5Y;FEMA No. 2709;AI3-36590;Methyl beta-propylacrylate;MFCD00048798;methyl hexaenoate;Methyl-beta-propylacrylate;DTXSID2062375;Q6M9281R5Y;trans-2-Hexenoic acid methyl ester;AKOS025243322;SY015809;SY112209;FT-0628815;FT-0628918

Chemical Property of 2-Hexenoic acid, methyl ester

Chemical Property:

• Vapor Pressure: 4.06mmHg at 25°C
• Melting Point: 32 °C
• Refractive Index: 1.427
• Boiling Point: 149.3 °C at 760 mmHg
• Flash Point: 45.4 °C
• PSA: 26.30000
• Density: 0.908 g/cm³
• LogP: 1.51570
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

METHYL 2-HEXENOATE AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CC(=O)OC
• Description: Methyl 2-hexenoate has a green, musty, earthy, sweet, fruity odor with a very powerful, sharp, green-fruity flavor. May be prepared by boiling the corresponding acid with methanol in the presence of concentrated H2S04 in chloroform and subsequent elimination of water from the vapors using MgS04; also from 3-chloropropionic acid methyl ester and anhydrous sodium acetate in acetic acid.

Technology Process of 2-Hexenoic acid, methyl ester

There total 2 articles about 2-Hexenoic acid, methyl 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:

1-hexene (592-41-6,25067-06-5) + C20H36O4 → methyl crotonate (623-43-8,4358-59-2,18707-60-3,130981-57-6) + methyl 2-pentenoate (15790-87-1,15790-88-2,818-59-7) + methyl 2-hexenoate (2396-77-2) + methyl (Z)-16-nonadecenoate (1220779-50-9) + Methyl-cis-octa-dec-2-enoat (17257-44-2) + 16-octadecenoic acid, methyl ester (42199-41-7) + C20H38O2 + C21H40O2 + C21H40O2

Guidance literature:

1-hexene; With (1,2-bis{(di-tertbutylphosphino)methyl}benzene)Pd(OTFf)₂; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

C₂₀H₃₆O₄; With Hoveyda-Grubbs catalyst second generation; p-benzoquinone; In n-heptane; dichloromethane; at 40 ℃; for 0.333333h; Schlenk technique;

DOI:10.1002/anie.201702796

Reference yield:

methyl 3-hexenoate (2396-78-3) → methyl 2-hexenoate (2396-77-2) + E,Z-4-hexenecarboxylic acid methyl ester (2396-79-4)

Guidance literature:

With acetylacetonatodicarbonylrhodium(l); carbon monoxide; hydrogen; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); In toluene; at 90 ℃; for 16h; under 11251.1 Torr; Autoclave;

DOI:10.1021/acscatal.7b00249

Reference yield: 85.0%

methyl 2-hexenoate (2396-77-2) + 3-methoxyphenylboronic acid (10365-98-7,1107579-37-2) → methyl (S)-3-(3-methoxyphenyl)hexanoate

Guidance literature:

With (1R,4R,7R)-N-(tert-butyl)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxamide; potassium carbonate; In water; toluene; at 100 ℃; for 16h; Reagent/catalyst; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jacs.5b02213

upstream raw materials:

1-hexene

methyl 3-hexenoate

Downstream raw materials:

(2R,3R)-3-Propyl-oxirane-2-carboxylic acid methyl ester

methyl 3-oxohexanoate

2-hydroxyhexanoic acid methyl ester

methyl 3-hydroxyhexanoate

Refernces

• 1、 Gaide, Tom,Bianga, Jonas,Schlipk?ter, Kim,Behr, Arno,Vorholt, Andreas J.. "Linear Selective Isomerization/Hydroformylation of Unsaturated Fatty Acid Methyl Esters: A Bimetallic Approach". . p. 4163 - 4171. Retrieved 2017/06/19.