3-Ethynylthiophene

Base Information

• Chemical Name: 3-Ethynylthiophene
• CAS No.: 67237-53-0
• Molecular Formula: C6H4S
• Molecular Weight: 108.164
• Hs Code.: 29349990
• European Community (EC) Number: 628-793-4
• DSSTox Substance ID: DTXSID70393537
• Nikkaji Number: J624.401G
• Wikidata: Q72477896
• Mol file: 67237-53-0.mol

Synonyms:3-Ethynylthiophene;67237-53-0;Thiophene, 3-ethynyl-;3-Thienylacetylene;MFCD04039973;3-Ethynyl thiophene;3-Ethynyl-thiophene;3-Ethynylthiophene, 96%;SCHEMBL28839;DTXSID70393537;MJHLPKWONJUCFK-UHFFFAOYSA-N;AMY15559;BBL103875;STL557685;AKOS010651616;AC-7562;CS-W011287;SB66955;AS-40389;E0892;FT-0645319;EN300-206297;A835677;J-512448

Chemical Property of 3-Ethynylthiophene

Chemical Property:

• Refractive Index: n20/D 1.5800(lit.)
• Boiling Point: 149.969 °C at 760 mmHg
• Flash Point: 28.358 °C
• PSA: 28.24000
• Density: 1.113 g/cm³
• LogP: 1.72940
• Storage Temp.: Room temperature.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 108.00337130
• Heavy Atom Count: 7
• Complexity: 98

Purity/Quality:

99% ^*data from raw suppliers

3-Ethynylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-37/38-41
• Safety Statements: 16-26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CSC=C1
• Uses: 3-Ethynylthiophene is used in preparation of benzothiazonines by rhodium-catalyzed denitrogenative annulation reactions of sulfonylaryltriazoles with thiochromones. 3-Ethynylthiophene may be used in the synthesis of the following:1-(2-bromobenzyl)-4-(thiophen-3-yl)-1H-1,2,3-triazole which is obtained by heating with 2-iodophenylethylazide in the presence of copper acetate monohydrate catalyst in N-methyl-2-pyrrolidoneN-benzyl-1-phenyl-5-(thiophen-3-yl)-4-pentyn-2-amine via a multi-step reaction process[(C4H3S-3)C≡CAg]n, a polymeric compound obtained via reaction with silver nitrate in the presence of triethylamine in acetonitrile4,5-bis(thiophen-3-ylethynyl)phthalonitrile via Sonogashira cross-coupling reaction with 4,5-dichlorophthalonitrile

Technology Process of 3-Ethynylthiophene

There total 15 articles about 3-Ethynylthiophene 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: 83.0%

3-(trimethylsilylethynyl)thiophene (130995-13-0) → 3-ethynylthiophene (67237-53-0)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1021/jacs.6b10374

Reference yield: 81.0%

2-methyl-4-(thiophen-3-yl)but-3-yn-2-ol (133844-85-6) → 3-ethynylthiophene (67237-53-0)

Guidance literature:

With potassium hydroxide; In methanol; benzene; at 75 ℃; for 14h; Heating;

Reference yield: 80.0%

3-thienyl iodide (10486-61-0) + mono-pivaloyloxyzinc acetylide → 3-ethynylthiophene (67237-53-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01892

upstream raw materials:

3-Bromothiophene

2-methyl-but-3-yn-2-ol

3-(2,2-dibromoethenyl)-thiophene

2-methyl-4-(thiophen-3-yl)but-3-yn-2-ol

Downstream raw materials:

trimethyl-(4-thiophen-3-ylethynyl-phenylethynyl)-silane

1-phenyl-2-(3-thienyl)ethyne

C₁₄H₁₂O₂S

1-(1-ethoxyethoxy)-2-(3-thienylethynyl)benzene

Refernces

• 1、 Varga, Bálint,Tóth, Balázs L.,Béke, Ferenc,Csenki, János T.,Kotschy, András,Novák, Zoltán. "Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block". supporting information. p. 4925 - 4929. Retrieved 2021/07/01.
• 2、 Weingand, Vanessa,Wurm, Thomas,Vethacke, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Rudolph, Matthias,Rominger, Frank,Xie, Jin,Hashmi, A. Stephen K.. "Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes". supporting information. p. 3725 - 3728. Retrieved 2018/02/23.