2-Ethynyl-4-methyl-phenol

Base Information

• Chemical Name: 2-Ethynyl-4-methyl-phenol
• CAS No.: 183589-14-2
• Molecular Formula: C9H8 O
• Molecular Weight: 132.15922
• DSSTox Substance ID: DTXSID20440621
• Nikkaji Number: J1.560.392E
• Wikidata: Q82256978
• Mol file: 183589-14-2.mol

Synonyms:2-ethynyl-4-methyl-phenol;2-ETHYNYL-4-METHYLPHENOL;183589-14-2;SCHEMBL1121945;DTXSID20440621;YGIBPZOCPTYZCL-UHFFFAOYSA-N;AKOS006240000;EN300-1855816

Chemical Property of 2-Ethynyl-4-methyl-phenol

Chemical Property:

• Vapor Pressure: 0.06mmHg at 25°C
• Refractive Index: 1.575
• Boiling Point: 224.741°C at 760 mmHg
• Flash Point: 99.854°C
• PSA: 20.23000
• Density: 1.093g/cm³
• LogP: 1.68190
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 132.057514874
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

97% ^*data from raw suppliers

2-ETHYNYL-4-METHYL-PHENOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Ethynyl-4-methyl-phenol

There total 7 articles about 2-Ethynyl-4-methyl-phenol 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: 84.0%

2-iodo-4-methylphenol (16188-57-1) + trimethylsilylacetylene (1066-54-2) → 2-ethynyl-4-methylphenol (183589-14-2)

Guidance literature:

2-iodo-4-methylphenol; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 23 ℃; for 3h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/acs.orglett.0c01096

Reference yield: 65.0%

4-methyl-2-(2-(trimethylsilyl)-ethynyl)phenol (183589-03-9) → 2-ethynyl-4-methylphenol (183589-14-2)

Guidance literature:

With potassium fluoride; In methanol; at 25 ℃; for 2h;

DOI:10.1021/jo961051a

Reference yield: 64.0%

tert-butyl(dimethyl){4-methyl-2-[(trimethylsilyl)ethynyl]phenoxy} silane (1431639-00-7) → 2-ethynyl-4-methylphenol (183589-14-2)

Guidance literature:

With tetra-n-butylammoniumfluoride trihydrate; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1002/anie.201310280

upstream raw materials:

4-methyl-2-(2-(trimethylsilyl)-ethynyl)phenol

2-iodo-4-methylphenol

2-bromo-p-cresol

trimethylsilylacetylene

Downstream raw materials:

5-methyl-2-(4-methylphenyl)benzofuran

2-(2-ethynyl-4-methylphenoxy)ethyl 4-bromobenzenesulfonate

(E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate

5-methyl-benzofuran-3-one

Refernces

• 1、 Dai, Ning,Hu, Weican,Qian, Guoying,Rong, Zhouting. "A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones". supporting information. p. 3286 - 3290. Retrieved 2020/04/21.
• 2、 Bucher, Janina,Wurm, Thomas,Nalivela, Kumara Swamy,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.. "Cyclization of gold acetylides: Synthesis of vinyl sulfonates via gold vinylidene complexes". . p. 3854 - 3858. Retrieved 2014/05/06.