16563-14-7

Basic information

• Product Name: 4-CYANO-3-TETRAHYDROTHIOPHENONE
• Synonyms: 4-CYANO-3-OXOTETRAHYDROTHIOPHENE;4-CYANO-3-TETRAHYDROTHIOPHENONE;4-OXOTETRAHYDROTHIOPHENE-3-CARBONITRILE;Cyanotetrahydrothiophenone;4-CYANO-3-TETRAHYDROTHIOPHENONE 98+%;3-Oxotetrahydrothiophene-4-carbonitrile;Nsc298357;4-Cyanotetrahydro-3-thiophenone
• CAS NO: 16563-14-7
• Molecular Formula: C₅H₅NOS
• Molecular Weight: 127.16
• Mol File: 16563-14-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 125 °C / 1mmHg
• Flash Point: 141.4°C
• Appearance: /
• Density: 1.29
• Storage Temp.: 2-8°C(protect from light)
• Solubility: soluble in Methanol
• CAS DataBase Reference: 4-CYANO-3-TETRAHYDROTHIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANO-3-TETRAHYDROTHIOPHENONE(16563-14-7)
• EPA Substance Registry System: 4-CYANO-3-TETRAHYDROTHIOPHENONE(16563-14-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16563-14-7(Hazardous Substances Data)

Usage

General Description

4-Cyano-3-tetrahydrothiophenone is a chemical compound primarily used in the industry for synthetic applications. It has the molecular formula C7H9NOS, with a molecular weight of 153.22 g/mol. Its systematic name is 4-Cyano-3,4-dihydro-2H-thiophen-3-one. Specific physical characteristics, possible toxicity or potential reactions, and safety measures for handling this chemical are not readily available and may vary depending on its purity and specific use. Therefore, it is crucial to use appropriate and careful practices when handling 4-Cyano-3-tetrahydrothiophenone or any similar chemical compounds.

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 107-13-1 acrylonitrile 

Downstream Products

• 146496-39-1 Toluene-4-sulfonic acid 4-cyano-2,5-dihydro-thiophen-3-yl ester 
• 214542-51-5 2-(3-Chloro-phenyl)-2,6-dihydro-4H-thieno[3,4-c]pyrazol-3-ylamine 
• 214542-49-1 2-(4-Methoxy-phenyl)-2,6-dihydro-4H-thieno[3,4-c]pyrazol-3-ylamine 
• 95469-88-8 2-phenyl-4,6-dihydro-2H-thieno[3,4-c]pyrazol-3-amine 
• 214542-52-6 2-(4-chlorophenyl)-2,6-dihydro-4H-thieno[3,4-c]pyrazol-3-amine 
• 214542-59-3 2-tert-butyl-2,6-dihydro-4H-thieno[3,4-c]pyrazol-3-amine 
• 104239-08-9 3-Benzyl-4-oxo-tetrahydro-thiophene-3-carbonitrile 
• 104239-15-8 4-Oxo-3-(3-phenyl-propyl)-tetrahydro-thiophene-3-carbonitrile 
• 104239-10-3 3-(4-Cyano-benzyl)-4-oxo-tetrahydro-thiophene-3-carbonitrile 
• 61325-28-8 3-(2-Aminoanilino)-2,5-dihydrothiophene-4-nitrile 
• 1012311-88-4 Methyl 2-[4-(3-cyano-4-oxothiolan-3-ylmethyl)phenyl]propionate 
• 1414568-68-5 phenyl 2-phenyl-4,6-dihydro-2H-thieno[3,4-c]pyrazol-3-ylcarbamate 
• 1414568-66-3 phenyl (5,5-dioxido-2-phenyl-4,6-dihydro-2H-thieno[3,4-c]pyrazol-3-yl)carbamate 
• 1414553-98-2 1-((3S,4R)-4-(3,4-difluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(5,5-dioxido-2-phenyl-4,6-dihydrothieno[3,4-c]pyrazol-3-yl)urea 

Relevant articles and documents

Unprecedented Demonstration of Regioselective SEAr Reaction giving Unsymmetrical Regioregular Oligothiophenes

Aromatization of 4-cyano-3-oxotetrahydrothiophene by sulfuryl chloride gives the new building block 4-cyano-3-pyrrolidylthiophene, which forms unsymmetrical regioregular oligothiophenes with a strict alternation of the donor and acceptor groups along the conjugated system. The self-coupling reactions that form the oligomers are shown to proceed by a regioselective electrophilic aromatic substitution mechanism involving a stabilized Wheland intermediate. First alternate: Regioregular oligothiophenes based on the 3-pyrrolidyl-4-cyanothiophene building block, with a strict alternation of the donor and acceptor groups along the conjugated backbone, have been prepared in one step. The mechanism of formation of the oligomers corresponds to a regioselective self-electrophilic aromatic substitution (self-SEAr) involving a stabilized Wheland intermediate.

A New Simple Synthesis of α-Substituted Acrylonitriles

An efficient preparation of α-substituted acrylonitriles 6 based on the utilization of 4-cyano-3-ketothiolane enolate anion (3) as a synthetic equivalent to α-acrylonitrile anion (1) is described.