3-Thiopheneacetonitrile

Base Information

• Chemical Name: 3-Thiopheneacetonitrile
• CAS No.: 13781-53-8
• Molecular Formula: C6H5NS
• Molecular Weight: 123.178
• Hs Code.: 29349990
• European Community (EC) Number: 237-433-1
• DSSTox Substance ID: DTXSID80160318
• Nikkaji Number: J209.038D
• Wikidata: Q72508787
• Mol file: 13781-53-8.mol

Synonyms:3-Thiopheneacetonitrile;13781-53-8;2-(Thiophen-3-yl)acetonitrile;Thiophene-3-acetonitrile;3-Thienylacetonitrile;3-cyanomethylthiophene;2-thiophen-3-ylacetonitrile;C6H5NS;2-(3-thienyl)acetonitrile;EINECS 237-433-1;MFCD00005471;thiophene-3-acetonitril;3-Thienylacetonitrile #;thiophen-3-yl-acetonitrile;SCHEMBL38504;BIDD:GT0037;3-Thiopheneacetonitrile, 96%;C6-H5-N-S;DTXSID80160318;HMS1784K13;AMY21841;AKOS001144602;PB19846;AC-18966;AS-14547;BP-12656;CS-0040874;FT-0616404;T1193;EN300-15001;W-110353;F0001-0473;Z111869576

Chemical Property of 3-Thiopheneacetonitrile

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 0.0316mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 243.7 °C at 760 mmHg
• Flash Point: 92.4 °C
• PSA: 52.03000
• Density: 1.171 g/cm³
• LogP: 1.81418
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 123.01427034
• Heavy Atom Count: 8
• Complexity: 113

Purity/Quality:

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

Thiophene-3-acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 20/21/22-36/37/38-23/24/25
• Safety Statements: 26-36/37-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC=C1CC#N
• Uses: 3-Thiopheneacetonitrile was used in the synthesis of:(E)-3-phenyl-2-(3-thienyl) acrylonitrile(Z)-3-(4-methylphenyl)-2-(3-thienyl) acrylonitrile

Technology Process of 3-Thiopheneacetonitrile

There total 10 articles about 3-Thiopheneacetonitrile 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: 78.0%

3-chlorothiophene (17249-80-8) + sodium cyanoacetate (1071-36-9) → (thiophen-3-yl)acetonitrile (13781-53-8)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)); In 1,3,5-trimethyl-benzene; at 20 - 140 ℃; for 5.16667h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201006763

Reference yield: 53.0%

Thien-3-ylboronic acid (6165-69-1) + chloroacetonitrile (107-14-2) → (thiophen-3-yl)acetonitrile (13781-53-8)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/ol503213z

Reference yield: 44.0%

3-Bromomethylthiophene (34846-44-1) + sodium cyanide (143-33-9,25596-52-5) → (thiophen-3-yl)acetonitrile (13781-53-8)

Guidance literature:

tetrabutylammomium bromide; In dichloromethane; water; Heating / reflux;

upstream raw materials:

3-Bromomethylthiophene

sodium cyanide

potassium cyanide

3-thiophene carboxaldehyde

Downstream raw materials:

(Z)-3-Thiophen-2-yl-2-thiophen-3-yl-acrylonitrile

(Z)-3-Dimethylamino-2-thiophen-3-yl-acrylonitrile

7-phenyl-4,5-dihydrothieno<2,3-c>pyridine

N-<2-(3-thienyl)ethyl>benzamide

Refernces

• 1、 Abdel-Fattah, Mohamed A. O.,Abadi, Ashraf H.,Lehmann, Jochen,Schweikert, Peter M.,Enzensperger, Christoph. "D1-like receptors distinguishing thieno-azecine regioisomers". . p. 1679 - 1686. Retrieved 2015/09/21.
• 2、 Pierre, Cathleen,Baudoin, Olivier. "Intramolecular PdII-catalyzed dehydrogenative C(sp 3)-C(sp2) coupling: An alternative to Pd 0-catalyzed C(sp3)-H arylation from aryl halides?". . p. 4473 - 4478. Retrieved 2013/06/26.