Methyl hept-2-ynoate

Base Information

• Chemical Name: Methyl hept-2-ynoate
• CAS No.: 18937-78-5
• Molecular Formula: C8H12 O2
• Molecular Weight: 140.182
• Hs Code.: 2916190090
• European Community (EC) Number: 242-689-2
• NSC Number: 129339
• DSSTox Substance ID: DTXSID10172348
• Nikkaji Number: J114.214C
• Wikidata: Q83042449
• Mol file: 18937-78-5.mol

Synonyms:Methyl hept-2-ynoate;methyl 2-heptynoate;18937-78-5;Methyl-2-heptynoate;2-Heptynoic acid, methyl ester;METHYL2-HEPTYNOATE;EINECS 242-689-2;Hept-2-ynoic acid methyl ester;Methyl 2-heptynate;Heptinsauremethylester;Ethyl2,3-dicyanopropionate;SCHEMBL1088279;DTXSID10172348;MFCD00048854;NSC129339;AKOS006228390;NSC 129339;NSC-129339;CS-0297332;FT-0693587;EN300-787186

Chemical Property of Methyl hept-2-ynoate

Chemical Property:

• Vapor Pressure: 0.255mmHg at 25°C
• Boiling Point: 205.1°Cat760mmHg
• Flash Point: 76.9°C
• PSA: 26.30000
• Density: 0.951g/cm³
• LogP: 1.35300
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC#CC(=O)OC

Technology Process of Methyl hept-2-ynoate

There total 11 articles about Methyl hept-2-ynoate 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: 95.0%

methyl chloroformate (79-22-1) + hex-1-yne (693-02-7) → methyl 2-heptynoate (18937-78-5)

Guidance literature:

hex-1-yne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.33333h; Inert atmosphere; Schlenk technique;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201304284

Reference yield: 94.0%

N-phenyl-N-((trifluoromethyl)sulfonyl)hept-2-ynamide + sodium methylate (124-41-4) → methyl 2-heptynoate (18937-78-5)

Guidance literature:

In methanol; at 50 ℃; for 2h;

DOI:10.1016/j.tet.2019.05.027

Reference yield: 72.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + hex-1-yne (693-02-7) → methyl 2-heptynoate (18937-78-5) + (E)-methyl 3-methoxyhept-2-enoate (182617-97-6)

Guidance literature:

With bis(benzonitrile)palladium(II) chloride; silver trifluoromethanesulfonate; N-{(1E,2E)-2-[(2,6-diisopropylphenyl)imino]acenaphthenylidene}-2,6-diisopropylaniline; p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 42h; under 3000.3 Torr; Autoclave; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201600521

upstream raw materials:

methanol

hept-2-ynoic acid

carbon monoxide

n-hexynyl(phenyl)iodonium tosylate

Downstream raw materials:

(E)-1-methoxycarbonyl-2-phenylsulphinylhex-1-ene

(2E,4E)-methyl hepta-2,4-dienoate

C₂₀H₂₇NO₄

(Z)-methyl 3-[benzoyl(p-tolyl)carbamoyl]hept-2-enoate

Refernces

• 1、 Grams, R. Justin,Lawal, Monsurat M.,Szwetkowski, Connor,Foster, Daniel,Rosenblum, Carol Ann,Slebodnick, Carla,Welborn, Valerie Vaissier,Santos, Webster L.. "Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies". supporting information. p. 172 - 178. Retrieved 2021/10/14.
• 2、 Xia, Xuanshu,Lao, Zhiqi,Toy, Patrick H.. "Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones". supporting information. p. 1100 - 1104. Retrieved 2019/05/24.