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:

95%, 99% ^*data from raw suppliers

2-Thiophenecarbonitrile ^*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

• 1、 Azath, Ismail Abulkalam,Suresh, Palaniswamy,Pitchumani, Kasi. "Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6]". . p. 2334 - 2339. Retrieved 2012.
• 2、 Krayushkin, M. M.,Kalik, M. A.,Kudryavtseva, A. Ya.. "SYNTHESIS OF 3-THIENYL-SUBSTITUTED ISOTHIAZOLINES-2- AND 1,2,4-THIADIAZOLES BASED ON NITRILE SULFIDES OF THE THIOPHENE SERIES". . p. 1477 - 1481. Retrieved 1992.
• 3、 Li, Yingguang,Shang, Sensen,Wang, Lianyue,Lv, Ying,Niu, Jingyang,Gao, Shuang. "Selectivity-tunable amine aerobic oxidation catalysed by metal-free N,O-doped carbons". . p. 12251 - 12254. Retrieved 2019.
• 4、 Nandurkar, Nitin S.,Bhanage, Bhalchandra M.. "Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed Suzuki, Heck, Sonogashira, and cyanation reactions". . p. 3655 - 3660. Retrieved 2008.
• 5、 Cao, Yu-Qing,Qu, An-Li,Liu, Rui-Yan,Duan, Chun-Ming. "A one-pot conversion of carboxylic acids into nitriles catalysed by PEG400 under microwave irradiation". . p. 414 - 415. Retrieved 2010.
• 6、 Noh, Ji-Hyun,Kim, Jinho. "Aerobic Oxidative Conversion of Aromatic Aldehydes to Nitriles Using a Nitroxyl/NOx Catalyst System". . p. 11624 - 11628. Retrieved 2015.
• 7、 Meltzer et al.. "-". . p. 4062,4064. Retrieved 1955.
• 8、 Saednya, Akbar. "A Mild, High-Yield Conversion of Aldoximes into Nitriles using Trichloroacetyl Chloride/Triethylamine". . p. 748 - 749. Retrieved 1983.
• 9、 Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo. "Br?nsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature". . p. 3005 - 3008. Retrieved 2017.
• 10、 Chang, Guoliang,Li, Xiaoyan,Zhang, Peng,Yang, Wenjing,Li, Kai,Wang, Yajie,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter. "Lewis acid promoted dehydration of amides to nitriles catalyzed by [PSiP]-pincer iron hydrides". . . Retrieved 2020.