18387-92-3

Basic information

• Product Name: 2-(TRIMETHYLSILYL)-5-METHYLTHIOPHENE
• Synonyms: 5-METHYL-2-TRIMETHYLSILYL-THIOPHENE;2-(TRIMETHYLSILYL)-5-METHYLTHIOPHENE;5-Methyl-2-trimethylsilanyl-thiophene
• CAS NO: 18387-92-3
• Molecular Formula: C₈H₁₄SSi
• Molecular Weight: 170.35
• Mol File: 18387-92-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 187.5°Cat760mmHg
• Flash Point: 67.2°C
• Appearance: /
• Density: 0.94g/cm³
• CAS DataBase Reference: 2-(TRIMETHYLSILYL)-5-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIMETHYLSILYL)-5-METHYLTHIOPHENE(18387-92-3)
• EPA Substance Registry System: 2-(TRIMETHYLSILYL)-5-METHYLTHIOPHENE(18387-92-3)

Safety Data

• Hazardous Substances Data: 18387-92-3(Hazardous Substances Data)

Usage

General Description

2-(trimethylsilyl)-5-methylthiophene is a chemical compound that belongs to the family of organosilicon compounds. It is a derivative of thiophene, which is a five-membered heterocyclic compound consisting of four carbon atoms and one sulfur atom. The trimethylsilyl group is a common functional group in organosilicon chemistry, and it is used as a protecting group for alcohols and a synthetic intermediate for various organic reactions. 2-(trimethylsilyl)-5-methylthiophene is commonly used in the synthesis of organic and pharmaceutical compounds due to its reactivity and functional group compatibility.

Upstream product

• 554-14-3 2-Methylthiophene 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 554-14-3 2-Methylthiophene 
• 1174754-36-9 5-(4-(dimethylamino)phenyl)-3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-(trimethylsilyl)thiophen-3-yl)cyclopent-1-enyl)thiophene-2-carbaldehyde 
• 1273574-15-4 4-(2-methyl-5-trimethylsilanylthiophen-3-yl)-benzaldehyde 
• 1273574-17-6 4-(2-methyl-5-trimethylsilanylthiophen-3-yl)-benzonitrile 

Relevant articles and documents

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.