Thiophene-2-carbonitrile

Base Information

• Chemical Name: Thiophene-2-carbonitrile
• CAS No.: 1003-31-2
• Molecular Formula: C5H3NS
• Molecular Weight: 109.152
• Hs Code.: 29349990
• European Community (EC) Number: 213-706-0
• DSSTox Substance ID: DTXSID10143114
• Nikkaji Number: J147.941E
• Wikidata: Q72508810
• Metabolomics Workbench ID: 127417
• ChEMBL ID: CHEMBL2229531
• Mol file: 1003-31-2.mol

Synonyms:2-Thiophenecarbonitrile;Thiophene-2-carbonitrile;1003-31-2;2-Cyanothiophene;2-Thiophene carbonitrile;Thiophenecarbonitrile;C5H3NS;MFCD00005416;EINECS 213-706-0;2-thenonitrile;2-Thenylcyanide;2-thiophenenitrile;2-cyano-thiophene;2-Thiophenonitrile;2-thiophencarbonitrile;thiopene-2-carbonitrile;SCHEMBL12605;BIDD:GT0001;2-Thiophenecarbonitrile, 99%;CHEMBL2229531;CUPOOAWTRIURFT-UHFFFAOYSA-;DTXSID10143114;HMS1788B13;STL299669;AKOS000121546;CS-W004699;PS-9266;AM20070640;FT-0633227;T2121;EN300-17512;A800100;W-108967;Z56946090;F1967-1444

Chemical Property of Thiophene-2-carbonitrile

Chemical Property:

• Appearance/Colour: Clear yellow brown liquid.
• Vapor Pressure: 0.476mmHg at 25°C
• Melting Point: 125-134 °C (decomp)
• Refractive Index: n20/D 1.563(lit.)
• Boiling Point: 193 °C at 760 mmHg
• Flash Point: 53.3 °C
• PSA: 52.03000
• Density: 1.172 g/cm³
• LogP: 1.61978
• Storage Temp.: Flammables area
• Water Solubility.: Slightly miscible with water.
• 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:

99% ^*data from raw suppliers

2-Thiophenecarbonitrile 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,F
• Hazard Codes: Xn,Xi,F
• Statements: 10-22-37/38-41-20/21/22-36/37/38
• Safety Statements: 26-39-36/37-16-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C#N
• Uses: 2-Thiophenecarbonitrile (2-Cyanothiophene) was used in the preparation of thiaplatinacycles. It was also used in the synthesis of 2,2′-thienylpyrroles.

Technology Process of Thiophene-2-carbonitrile

There total 132 articles about Thiophene-2-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: 100.0%

thiophene-2-carbaldehyde (98-03-3) → thiophene-2-carbonitrile (1003-31-2)

Guidance literature:

With trimethylsilylacetylene; zinc(II) chloride; In chloroform; for 4h; Heating;

DOI:10.1016/S0040-4020(01)90003-1

Reference yield: 99.0%

2-thiophenemethanol (636-72-6) → thiophene-2-carbonitrile (1003-31-2)

Guidance literature:

2-thiophenemethanol; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With ammonia; iodine; In dichloromethane; water; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0033-1338489

Reference yield: 95.0%

thiophene-2-carbaldehyde oxime (38266-87-4) → thiophene-2-carbonitrile (1003-31-2)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 4 A molecular sieve; In acetonitrile; at 80 ℃; for 0.166667h;

DOI:10.1021/ol0168768

upstream raw materials:

thiophene

bromocyane

ethanedinitrile

2-Methylthiophene

Downstream raw materials:

2-thiophenylcarboxamide

thiophene-2-carbothioamide

5-nitro-2-thienyl cyanide

4-nitrothiophene-2-carbonitrile

Refernces

Assembling p-type molecules on single wall carbon nanotubes for photovoltaic devices

10.1039/b904863d

The study focuses on the design and synthesis of an oligothiophene molecule, 5TPY, which noncovalently functionalizes single-wall carbon nanotubes (SWNTs) to create a hybrid material for photovoltaic devices. The purpose of this hybrid material is to leverage the excellent electron transfer abilities of SWNTs, their flexibility, and optical transparency to potentially enhance the performance of flexible organic solar cells. The chemicals used in the study include pyrene as the CNT-binding group due to its ability to adsorb to carbon nanotubes through π-π stacking interactions, a quinquethiophene segment as the electronically active segment, and various reagents in the synthesis process such as 2-thiophenecarbonitrile, NBS (N-bromosuccinimide), TFA (Trifluoroacetic acid), 1-pyrenebutyric acid, DPTS (N,N'-Dicyclohexylcarbodiimide), EDCI (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide), and tributyltin compounds. These chemicals serve to construct the 5TPY molecule and facilitate its assembly around the SWNTs, preserving the electronic properties of the nanotubes for use in photovoltaic applications.