Thiophene-3-carbonitrile

Base Information

• Chemical Name: Thiophene-3-carbonitrile
• CAS No.: 1641-09-4
• Molecular Formula: C5H3NS
• Molecular Weight: 109.152
• Hs Code.: 29341000
• European Community (EC) Number: 216-687-7
• DSSTox Substance ID: DTXSID40167707
• Nikkaji Number: J195.277C
• Wikidata: Q72508807
• Mol file: 1641-09-4.mol

Synonyms:3-Cyanothiophene;3-Thiophenecarbonitrile;1641-09-4;Thiophene-3-carbonitrile;3-Thiophene acetonitrile;MFCD00151852;Thiophene-3-nitrile;EINECS 216-687-7;SCHEMBL154729;3-Thiophenecarbonitrile, 95%;DTXSID40167707;BBL104398;STK503621;AKOS005255301;CS-W021912;PB27442;PS-9267;SY017477;AM20080462;FT-0616406;FT-0652381;EN300-43587;A851031;W-107948;Z57900046;F0001-0595;1-(2-tert-butylcyclohexoxy)butan-2-ol

Chemical Property of Thiophene-3-carbonitrile

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.423mmHg at 25°C
• Refractive Index: n20/D 1.5630(lit.)
• Boiling Point: 195.3 °C at 760 mmHg
• Flash Point: 71.9 °C
• PSA: 52.03000
• Density: 1.21 g/cm³
• LogP: 1.61978
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.99862027
• Heavy Atom Count: 7
• Complexity: 102

Purity/Quality:

98%,99%, ^*data from raw suppliers

Thiophene-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC=C1C#N
• Uses: 3-Thiophenecarbonitrile can be used to synthesize the following:2,4-dinaphthyl-3-cyanothiophene via reaction with iodonaphthalene2,5-bis-tri(n-butyl)tin-3-cyanothiophene, a building block for the synthesis of new alternating (3-alkyl/3-cyano)thiophene copolymers

Technology Process of Thiophene-3-carbonitrile

There total 48 articles about Thiophene-3-carbonitrile 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: 99.0%

3-hydroxymethyl-thiophene (71637-34-8) → 3-thiophenecarbonitrile (1641-09-4)

Guidance literature:

With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 5h; under 3750.38 Torr; Autoclave; High pressure;

DOI:10.1021/acscatal.0c00485

Reference yield: 98.0%

3-thiophene carboxaldehyde (498-62-4) → 3-thiophenecarbonitrile (1641-09-4)

Guidance literature:

With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; In dichloromethane; at 23 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01263

Reference yield: 90.0%

3-Bromothiophene (872-31-1) → 3-thiophenecarbonitrile (1641-09-4)

Guidance literature:

With sodium carbonate; potassium iodide; N,N`-dimethylethylenediamine; copper(II) bis(tetrafluoroborate); In N,N-dimethyl acetamide; at 140 ℃; for 16h;

DOI:10.1016/j.tetlet.2005.02.106

upstream raw materials:

3-thiophenecarboxaldehyde oxime

3-Methylthiophene

3-Bromothiophene

sodium cyanide

Downstream raw materials:

5-(thiophen-3-yl)-2H-tetrazole

2-bromo-4-cyanothiophene

N-phenyl thiophene carboxamidine-3

3-cyanothiophene-2-carboxylic acid

Refernces

• 1、 Hui, Yu,Luo, Qingsong,Qin, Yucai,Song, Lijuan,Wang, Hai,Wang, Liang,Xiao, Feng-Shou. "Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation". . p. 2164 - 2172. Retrieved 2021/09/20.
• 2、 De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio. "Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis". . . Retrieved 2021/11/10.