Ethyl 4-methylpent-2-ynoate

Base Information

• Chemical Name: Ethyl 4-methylpent-2-ynoate
• CAS No.: 38491-47-3
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Hs Code.: 2916190090
• DSSTox Substance ID: DTXSID10464639
• Nikkaji Number: J1.398.716E
• Wikidata: Q82290044
• Mol file: 38491-47-3.mol

Synonyms:Ethyl 4-methylpent-2-ynoate;38491-47-3;2-Pentynoic acid, 4-methyl-, ethyl ester;4-methyl-pent-2-ynoic acid ethyl ester;SCHEMBL497771;DTXSID10464639;VYXQGOIIOVRLKW-UHFFFAOYSA-N;EN300-227446

Chemical Property of Ethyl 4-methylpent-2-ynoate

Chemical Property:

• Vapor Pressure: 0.367mmHg at 25°C
• Boiling Point: 198.1oC at 760 mmHg
• Flash Point: 69.6oC
• PSA: 26.30000
• Density: 0.948g/cm3
• LogP: 1.20890
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 168

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CC(C)C

Technology Process of Ethyl 4-methylpent-2-ynoate

There total 10 articles about Ethyl 4-methylpent-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: 92.0%

1,1-dibromo-3-methyl-1-butene (32363-92-1) + chloroformic acid ethyl ester (541-41-3) → ethyl 4-methylpent-2-ynoate (38491-47-3)

Guidance literature:

1,1-dibromo-3-methyl-1-butene; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.5h;

chloroformic acid ethyl ester; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)01189-8

Reference yield: 84.2%

ethyl 4-methyl-3-{[(trifluoromethyl)sulfonyl]oxy}pent-2-enoate → ethyl 4-methylpent-2-ynoate (38491-47-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 80 ℃; for 16h; Inert atmosphere;

Reference yield: 84.2%

ethyl 4-methyl-2-[(trifluoromethane)sulfonyloxy]pent-2-enoate → ethyl 4-methylpent-2-ynoate (38491-47-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 80 ℃; for 16h; Inert atmosphere;

upstream raw materials:

ethyl 2-diazo-3-hydroxy-4-methylpentanoate

ethyl 4-methyl-3-oxo-2-(triphenylphosphoranylidene)pentanoate

1,1-dibromo-3-methyl-1-butene

chloroformic acid ethyl ester

Downstream raw materials:

(E)-ethyl 4-methyl-3-phenylpent-2-enoate

3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

(Z)-2-[(E)-3-(4-Methoxy-benzyloxy)-2-methyl-propenyl]-4-methyl-pent-2-enoic acid ethyl ester

ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate