77998-61-9

Usage

Uses

Used in Organic Synthesis:
4-Bromo-2-(trimethylsilyl)thiophene is used as a building block in organic synthesis for the construction of complex molecules. The presence of the bromine atom and the trimethylsilyl group allows for selective reactions and the introduction of various functional groups onto the thiophene ring, contributing to the development of pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4-Bromo-2-(trimethylsilyl)thiophene is used as a starting material for the synthesis of therapeutic agents. Its reactivity and the protective nature of the trimethylsilyl group enable the creation of diverse drug candidates with potential applications in treating various diseases and conditions.
Used in Agrochemical Development:
4-Bromo-2-(trimethylsilyl)thiophene is utilized as a key intermediate in the development of agrochemicals. Its ability to undergo substitution reactions and form complex molecules makes it a valuable component in the synthesis of pesticides, herbicides, and other agricultural chemicals designed to improve crop yield and protect against pests.
Used in Advanced Material Synthesis:
In the field of materials science, 4-Bromo-2-(trimethylsilyl)thiophene is employed as a precursor for the synthesis of advanced materials with unique properties. These materials can be used in various applications, such as electronic devices, sensors, and energy storage systems, owing to their tailored chemical and physical characteristics.

Upstream product

• 18246-28-1 2-bromo-5-trimethylsilylthiophene 
• 77998-63-1 (4,5-dibromothiophen-2-yl)trimethylsilane 

Downstream Products

• 872-31-1 3-Bromothiophene 

Relevant academic research and scientific papers

Base-catalyzed halogen dance reaction and oxidative coupling sequence as a convenient method for the preparation of dihalo-bisheteroarenes

Figure presented A one-pot preparation of the 2,2′-dibromo-1, 1′-bisheteroarenes 3a-d from bromo-heteroarenes utilizing the sequence of the base-catalyzed halogen dance (BCHD) reaction and CuCl2-promoted oxidative coupling of the in situ formed α-lithio-β-halo-heteroarenes 2a-d provides a convenient access to precursors for the preparation of tricyclic heteroaromatic cores. The structures of 3a,b,d, 6, and 9 were confirmed by single-crystal X-ray analysis, and dibromides 3a and 3b were used for the preparation of dithieno-[2,3-b:3′,2′-d]-pyrrole 10a and its selenophene analogue 10b, respectively.

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.