Methyl 2-octynoate

Base Information

• Chemical Name: Methyl 2-octynoate
• CAS No.: 111-12-6
• Deprecated CAS: 53073-28-2
• Molecular Formula: C9H14 O2
• Molecular Weight: 154.209
• Hs Code.: 29161900
• European Community (EC) Number: 203-836-6
• NSC Number: 72098
• UNII: 0TTP6YT2T3
• DSSTox Substance ID: DTXSID9047093
• Nikkaji Number: J22.135J
• Wikidata: Q27237243
• RXCUI: 1313237
• Metabolomics Workbench ID: 44803
• ChEMBL ID: CHEMBL3185035
• Mol file: 111-12-6.mol

Synonyms:methyl 2-octynoate;methyl heptine carbonate

Chemical Property of Methyl 2-octynoate

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Boiling Point: 217-220 °C(lit.)
• Flash Point: 192 °F
• PSA: 26.30000
• Density: 0.92 g/mL at 25 °C(lit.)
• LogP: 1.74310
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 171

Purity/Quality:

99.9% ^*data from raw suppliers

Methyl 2-Octynoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC#CC(=O)OC
• Description: Methyl 2-octynoate (also known as methyl 2-caprylate) is a kind of fatty acid ester formed by the esterfication between methanol and 2 -octynoate. It is a kind of useful flavor and fragrance agent. Methyl 2-octynoate has an odor similar to violets on dilution, and if concentrated, a powerful and unpleasant odor. It has a wineberry flavor (muscatel). It may be prepared from heptaldehyde via heptyne and heptyne carboxylic acid; the acid is subsequently esterified.
• Uses: Perfumery, flavoring. Methyl 2-octynoate may be used as a fragrance allergen standard for the quantification of the analyte in cosmetics using chromatography techniques.

Technology Process of Methyl 2-octynoate

There total 17 articles about Methyl 2-octynoate 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: 97.0%

1-Heptyne (628-71-7) + methyl chloroformate (79-22-1) → methyl 2-octynoate (111-12-6,53073-28-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) -78 deg C, 30 min, 2.) -78 deg C to r.t., 15 min;

DOI:10.1021/jo00119a043

Reference yield: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + oct-2-ynoic acid (5663-96-7) → methyl 2-octynoate (111-12-6,53073-28-2)

Guidance literature:

In diethyl ether;

DOI:10.1021/jo00261a001

Reference yield: 90.0%

oct-2-ynoic acid (5663-96-7) + methyl iodide (74-88-4) → methyl 2-octynoate (111-12-6,53073-28-2)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 10 - 15 ℃; for 24h;

DOI:10.1021/jo00033a048

upstream raw materials:

methanol

oct-2-ynoic acid

sodioheptyne

methyl chloroformate

Downstream raw materials:

methyl 3-oxooctanoate

methyl 3-methoxyoct-2-enoate

Methyl 3,3-dimethoxy-octanoate

2-octyn-1-ol

Refernces

• 1、 Tsuji, Jiro,Takahashi, Mitsuo,Takahashi, Takashi. "FACILE SYNTHESIS OF ACETYLENECARBOXYLATES BY THE OXIDATIVE CARBONYLATION OF TERMINAL ACETYLENES CATALYSED BY PdCl2 UNDER MILD CONDITIONS". . p. 849 - 850. Retrieved 1980.
• 2、 Hoffmann, Inga,Hamberg, Mats,Lindh, Roland,Oliw, Ernst H.. "Novel insights into cyclooxygenases, linoleate diol synthases, and lipoxygenases from deuterium kinetic isotope effects and oxidation of substrate analogs". . p. 1508 - 1517. Retrieved 2012.
• 3、 Rossi, Renzo,Bellina, Fabio,Carpita, Adriano,Mazzarella, Felice. "Palladium-mediated cross-coupling reactions involving 3-substituted alkyl (E)-2,3-dibromopropenoates and arylzinc or aryltin derivatives". . p. 4095 - 4110. Retrieved 1996.