2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester

Base Information

• Chemical Name: 2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester
• CAS No.: 7515-16-4
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• DSSTox Substance ID: DTXSID20485395
• Nikkaji Number: J1.059.721H
• Wikidata: Q82324547
• Mol file: 7515-16-4.mol

Synonyms:7515-16-4;2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester;methyl 3-(4-methylphenyl)prop-2-ynoate;Methyl3-(p-tolyl)propiolate;Methyl 3-(p-tolyl)propiolate;SCHEMBL11902648;DTXSID20485395;DJGUBOLDIRLMDR-UHFFFAOYSA-N;p-Tolyl-propynoic acid methyl ester;methyl 3-(4-methylphenyl)propynoate;AKOS013859462;3-(p-Tolyl)propiolic acid methyl ester;methyl 3-(4-methylphenyl)prop-2-inoate;EN300-743589

Chemical Property of 2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester

Chemical Property:

• Melting Point: 68-69 °C
• Boiling Point: 263.7±19.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 1.51950
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 235

Purity/Quality:

98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C#CC(=O)OC

Technology Process of 2-Propynoic acid, 3-(4-methylphenyl)-, methyl ester

There total 17 articles about 2-Propynoic acid, 3-(4-methylphenyl)-, 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: 100.0%

methanol (67-56-1) + 2-bromo-1-(4-tolyl)-3,3-difluorocyclopropene → methyl 3-(4-methylphenyl)prop-2-ynoate (7515-16-4)

Guidance literature:

Heating;

Reference yield: 89.0%

1-(2,2-dibromovinyl)-4-methylbenzene (60512-56-3) + methyl chloroformate (79-22-1) → methyl 3-(4-methylphenyl)prop-2-ynoate (7515-16-4)

Guidance literature:

1-(2,2-dibromovinyl)-4-methylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

Reference yield: 89.0%

carbon tetrabromide (558-13-4) + 4-methyl-benzaldehyde (104-87-0) + methyl chloroformate (79-22-1) → methyl 3-(4-methylphenyl)prop-2-ynoate (7515-16-4)

Guidance literature:

carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

4-methyl-benzaldehyde; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

methyl chloroformate; Further stages;

upstream raw materials:

methanol

3-(4-methylphenyl)prop-2-ynoic acid

methyl 2,3-dibromo-3-p-tolylpropionic acid methyl ester

5-p-Tolyl-2,4-dihydro-pyrazol-3-one

Downstream raw materials:

E-methyl β-piperidino-p-methylcinnamate

E-methyl β-morpholino-p-methylcinnamate

E-methyl β-(N,N-diethylamino)-p-methylcinnamate

2-p-tolyl-pyrazolo[1,5-b]pyridazine-3-carboxylic acid methyl ester

Refernces

• 1、 Wang, Dan,Lin, Junhui,Zhu, Yannan,Huang, You. "De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions". supporting information. p. 1873 - 1877. Retrieved 2021/02/16.
• 2、 Sugimoto, Kenji,Kosuge, Shuto,Sugita, Takae,Miura, Yuka,Tsuge, Kiyoshi,Matsuya, Yuji. "Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization". . p. 3981 - 3985. Retrieved 2021/05/26.