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
• General Description: 3-(Thien-2-yl)acrylonitrile 97, also known as 2-thiopheneacrylonitrile or 3-(2-thienyl)acrylonitrile, is a reactive organic compound featuring a thiophene ring conjugated with an acrylonitrile moiety. The referenced study demonstrates its utility as a key intermediate in reactions with triphenylphosphine alkylenes, where it participates in Michael additions and cyclization reactions to form diverse products such as cyclopropane derivatives, ylides, and pyran derivatives. The compound's reactivity is influenced by substituents and reaction conditions, underscoring its versatility in synthesizing structurally complex molecules with potential biological relevance.

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

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

3-(2-thienyl)acrylic acid

Refernces

The reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles

10.1080/10426500307778

The research investigates the reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles, aiming to explore the formation of various products under different reaction conditions and the influence of the substituents on the reaction outcomes. Key chemicals involved include ethyl 3-(2-thienyl)acrylocyanoacetate (1b), various ylides such as (methoxycarbonylmethylene)triphenylphosphorane (2a), (ethoxycarbonylmethylene)triphenylphosphorane (2b), (benzoylmethylene)triphenylphosphorane (2c), and (cyanomethylene)triphenylphosphorane (14). The study found that the initial Michael addition of ylides to the exocyclic methide carbon in 1b leads to diverse products depending on the nature of the ylide and reaction conditions. For instance, reactions with 2a and 2b in the presence of triethylamine yielded cyclopropane derivatives and new ylides, while the reaction with 2c in ethyl acetate containing benzoic acid produced a pyran derivative. The reaction of (cyanomethylene)triphenylphosphorane (14) with 1b resulted in a cyclopropane derivative, whereas with malonitrile 1a, it produced a ylide and a propene derivative. The research concludes that the substituents on the ylides and the reaction conditions significantly affect the reaction pathways and products, highlighting the versatility of these reactions in synthesizing complex organic compounds with potential biological activities.