77998-64-2

Basic information

• Product Name: 5-CYANO-2-TRIMETHYLSILYL-THIOPHENE
• Synonyms: 5-CYANO-2-TRIMETHYLSILYL-THIOPHENE;5-Cyano-2-trimethylsilanyl-thiophene;5-Trimethylsilanyl-thiophene-2-carbonitrile
• CAS NO: 77998-64-2
• Molecular Formula: C8H11NSSi
• Molecular Weight: 181.33014
• Mol File: 77998-64-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-CYANO-2-TRIMETHYLSILYL-THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CYANO-2-TRIMETHYLSILYL-THIOPHENE(77998-64-2)
• EPA Substance Registry System: 5-CYANO-2-TRIMETHYLSILYL-THIOPHENE(77998-64-2)

Safety Data

• Hazardous Substances Data: 77998-64-2(Hazardous Substances Data)

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 75-77-4 chloro-trimethyl-silane 

Relevant articles and documents

Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.

THE RATES OF BASE CLEAVAGE OF SUBSTITUTED 2-THIENYLTRIMETHYLSILANES. AB INITIO CALCULATIONS OF THE ACIDITIES OF MONOSUBSTITUTED THIOPHENS

Rates of cleavage in NaOMe-MeOH at 50 deg C have been determined for the mono-substituted 2-trimethylsilylthiophens X*C4H2S*SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2*C4HS*SiMe3-2.For several compounds the rate and product isotope effects have also been determined.The energies involved in the process X*C4H3S X*C4H2S- for deprotonation at the 2-position have been calculated by an ab initio method (STO-3G), and the results used in analysis of the substituent effects in the cleavage of the XC4H2S*SiMe3-2 compounds.The results are consistent with the view the aryl anions separate in the rate-determining step of the cleavage.The isotope effects are all close to unity, whereas by comparison with results for XC6H4CH2SiMe3 and related species of similar reactivity, values in the region of 10 would be expected for the 3- and 5-NO2 compounds if the product isotope effect for a carbanion R depended only in the pKa of RH.The difference between the thienyl- and benzyl-type anions is attributed to the absence of conjugative delocalization of the charge in the former. Approximate pKa values are derived for the 2-positions of the X*C4H3S compounds.