3-(2-Thienyl)acrylonitrile

Base Information

• Chemical Name: 3-(2-Thienyl)acrylonitrile
• CAS No.: 6041-28-7
• Molecular Formula: C7H5NS
• Molecular Weight: 135.189
• European Community (EC) Number: 227-928-0
• Nikkaji Number: J1.797.001A,J227.248B
• Wikidata: Q76306625
• Mol file: 6041-28-7.mol

Synonyms:6041-28-7;3-(2-Thienyl)acrylonitrile;3-(Thien-2-yl)acrylonitrile 97;EINECS 227-928-0;(2E)-3-(THIOPHEN-2-YL)PROP-2-ENENITRILE;(E)-3-thiophen-2-ylprop-2-enenitrile;3-(2-Thienyl)-acrylnitril;3-(2-Thienyl)propenenitrile;SCHEMBL522003;(E)-3-(2-Thienyl)acrylonitrile;2-Propenenitrile, 3-(2-thienyl)-;3-(THIEN-2-YL)ACRYLONITRILE;MFCD00022529;AKOS009159040;(2E)-3-(2-thienyl)-2-propenenitrile;NS-01060

Chemical Property of 3-(2-Thienyl)acrylonitrile

Chemical Property:

• Vapor Pressure: 0.00979mmHg at 25°C
• Refractive Index: 1.632
• Boiling Point: 264.3 °C at 760 mmHg
• Flash Point: 113.6 °C
• PSA: 52.03000
• Density: 1.193 g/cm³
• LogP: 2.28488
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 135.01427034
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C=CC#N
• Isomeric SMILES: C1=CSC(=C1)/C=C/C#N

Technology Process of 3-(2-Thienyl)acrylonitrile

There total 34 articles about 3-(2-Thienyl)acrylonitrile 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: 81.0%

2-thiophenemethanol (636-72-6) + acetonitrile (75-05-8,26809-02-9) → (2E)-3-(thiophen-2-yl)prop-2-enenitrile (6041-28-7,51791-11-8,26250-47-5)

Guidance literature:

With manganese(IV) oxide; sodium hydroxide; at 82 ℃; for 8h;

Reference yield: 77.0%

2-allylthiophene (20849-87-0) → (2E)-3-(thiophen-2-yl)prop-2-enenitrile (6041-28-7,51791-11-8,26250-47-5)

Guidance literature:

With trimethylsilylazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride; In 1,2-dichloro-ethane; at 60 ℃; for 2h;

DOI:10.1021/ja1070202

Reference yield: 75.0%

thiophene-2-carbaldehyde (98-03-3) + 2-trimethylsilylacetonitrile (18293-53-3) → (2Z)-3-(thiophen-2-yl)prop-2-enenitrile (6041-28-7,26250-47-5,51791-11-8) + (2E)-3-(thiophen-2-yl)prop-2-enenitrile (6041-28-7,51791-11-8,26250-47-5) + (±)-3-hydroxy-3-(thiophen-2-yl)propanenitrile (235085-83-3)

Guidance literature:

thiophene-2-carbaldehyde; 2-trimethylsilylacetonitrile; With tetra-n-butylammonium alginate; In toluene; at 20 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; water; In methanol; toluene; optical yield given as %de;

DOI:10.1016/j.tetlet.2012.02.012

upstream raw materials:

thiophene

acrylonitrile

2-Iodothiophene

thiophene-2-carbaldehyde

Downstream raw materials:

3-(2-thienyl)acrylic acid

3-(3-Benzoyl-thioureido)-4-thiophen-2-ylmethyl-1H-pyrrole-2-carboxylic acid methyl ester

3-(3-Benzoyl-2-methyl-isothioureido)-4-thiophen-2-ylmethyl-1H-pyrrole-2-carboxylic acid methyl ester

Refernces

• 1、 Yang, Fan,Yu, Jiaojiao,Liu, Yun,Zhu, Jin. "Rhodium(III)-catalyzed oxadiazole-directed alkenyl C-H activation for synthetic access to 2-acylamino and 2-amino pyridines". supporting information. p. 9978 - 9987. Retrieved 2018/05/31.
• 2、 Zhang, Qi,Zhang, Linjing,Tang, Chaojun,Luo, Huan,Cai, Xuediao,Chai, Yonghai. "Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles". . p. 6935 - 6942. Retrieved 2016/10/14.