Methyl propiolate

Base Information

• Chemical Name: Methyl propiolate
• CAS No.: 922-67-8
• Molecular Formula: C4H4O2
• Molecular Weight: 84.0746
• Hs Code.: 29161980
• European Community (EC) Number: 213-083-5
• NSC Number: 154164
• UNII: T88NXO102K
• DSSTox Substance ID: DTXSID60238923
• Nikkaji Number: J87.385C
• Wikipedia: Methyl_propiolate
• Wikidata: Q56291556
• ChEMBL ID: CHEMBL4086262
• Mol file: 922-67-8.mol

Synonyms:METHYL PROPIOLATE;922-67-8;methyl prop-2-ynoate;2-Propynoic acid, methyl ester;Methyl acetylenecarboxylate;Methyl propynoate;Propiolic acid, methyl ester;Methyl ethynecarboxylate;methyl propargylate;Propynoic acid methyl ester;Propynoic acid, methyl ester;Acetylenecarboxylic acid methyl ester;MFCD00008572;methyl 2-propynoate;NSC 154164;EINECS 213-083-5;Propiolic Acid Methyl Ester;BRN 0605462;AI3-37828;T88NXO102K;NSC-154164;4-02-00-01688 (Beilstein Handbook Reference);27342-21-8;Propargylic Acid Methyl Ester;methyl propalate;Methyl propiolate, 99%;propiolic acid methylester;UNII-T88NXO102K;methyl acetylenemonocarboxylate;(CARBOMETHOXY)ACETYLENE;CHEMBL4086262;(METHOXYCARBONYL)ACETYLENE;AMY7053;DTXSID60238923;NSC154164;STK505661;AKOS000120024;SB40750;BP-30045;LS-123962;CS-0022413;FT-0628338;P0528;EN300-20478;P17723;J-522627;F0001-2227

Chemical Property of Methyl propiolate

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 31.438mmHg at 25°C
• Melting Point: 171-173 °C
• Refractive Index: n20/D 1.408(lit.)
• Boiling Point: 104 °C at 760 mmHg
• Flash Point: 10 °C
• PSA: 26.30000
• Density: 1.028 g/cm³
• LogP: -0.20740
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• Water Solubility.: Not miscible in water.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 84.021129366
• Heavy Atom Count: 6
• Complexity: 95.4

Purity/Quality:

99% ^*data from raw suppliers

Methyl Propiolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38-36
• Safety Statements: 26-36-36/37/39-23-16-33-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C#C
• Uses: Methyl propiolate was used in the synthesis of polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives. It was also used as a thiol derivatizing agent for capillary electrophoresis.

Technology Process of Methyl propiolate

There total 17 articles about Methyl propiolate 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: 84.5%

Propiolic acid (471-25-0) + trimethyl orthoformate (149-73-5) → propynoic acid methyl ester (922-67-8)

Guidance literature:

With sulfuric acid; In methanol; dichloromethane; at 40 ℃; for 28h;

Reference yield: 73.0%

carbon dioxide (124-38-9,18923-20-1) + propynoic acid methyl ester (922-67-8) → acetylenedicarboxylic acid monomethylester (922-67-8)

Guidance literature:

propynoic acid methyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

DOI:10.1039/c4ob02114b

Reference yield: 65.0%

methanol (67-56-1) + Propiolic acid (471-25-0) → propynoic acid methyl ester (922-67-8)

Guidance literature:

With sulfuric acid; for 48h;

DOI:10.3390/10111413

upstream raw materials:

methanol

Propiolic acid

methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate

(1S,3aS)-1H-1,3a-Etheno-azulene-9-carboxylic acid methyl ester

Downstream raw materials:

3-(1-hydroxycyclohexyl)propiolic acid

(1-hydroxy-2-methyl-cyclohexyl)-propiolic acid

1,5-pentanedioic acid

succinic acid

Refernces

• 1、 Yoshino,Komiyama,Shinomiya. "-". . p. 4482. Retrieved 1964.
• 2、 Hu, Linfeng,Cao, Weidi,Wang, Kaixuan,Liu, Xiaohua,Feng, Xiaoming. "Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles". supporting information. p. 13138 - 13141. Retrieved 2021/12/16.
• 3、 Hofer, Manuel,De Haro, Teresa,Gómez-Bengoa, Enrique,Genoux, Alexandre,Nevado, Cristina. "Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes". . p. 8411 - 8420. Retrieved 2019/09/30.