18246-28-1

Basic information

• Product Name: (5-broMothiophen-2-yl)triMethylsilane
• Synonyms: (5-broMothiophen-2-yl)triMethylsilane;2-Bromo-5-(trimethylsilyl)thiophene;IN1512, Silane, (5-bromo-2-thienyl)trimethyl-
• CAS NO: 18246-28-1
• Molecular Formula: C₇H₁₁BrSSi
• Molecular Weight: 235.21674
• Mol File: 18246-28-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 70°C/2mmHg(lit.)
• Appearance: /
• Refractive Index: 1.5330 to 1.5370
• CAS DataBase Reference: (5-broMothiophen-2-yl)triMethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (5-broMothiophen-2-yl)triMethylsilane(18246-28-1)
• EPA Substance Registry System: (5-broMothiophen-2-yl)triMethylsilane(18246-28-1)

Safety Data

• Hazardous Substances Data: 18246-28-1(Hazardous Substances Data)

Usage

Description

(5-Bromothiophen-2-yl)trimethylsilane, with the molecular formula C8H11BrSSi, is a colorless liquid chemical compound used extensively in organic synthesis and as a reagent for preparing various molecules. It is characterized by the presence of a bromine atom, a methyl group, and a trimethylsilyl group attached to a thiophene ring. Known for its ability to undergo various chemical reactions, such as cross-coupling reactions and functional group transformations, it is a valuable tool in the field of organic chemistry.

Uses

Used in Organic Synthesis:
(5-Bromothiophen-2-yl)trimethylsilane is used as a reagent for the preparation of various molecules, particularly in the field of organic chemistry. Its unique structure allows it to participate in cross-coupling reactions and functional group transformations, making it a versatile compound for creating a wide range of molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (5-Bromothiophen-2-yl)trimethylsilane is used as a building block for the synthesis of complex organic molecules, including potential drug candidates. Its ability to undergo various chemical reactions makes it a valuable tool in the development of new medications.
Used in Chemical Research:
(5-Bromothiophen-2-yl)trimethylsilane is also utilized in chemical research as a model compound to study the effects of different functional groups on the reactivity and properties of organic molecules. This helps researchers understand the underlying principles of chemical reactions and develop new synthetic strategies.
Used in Material Science:
In the field of material science, (5-Bromothiophen-2-yl)trimethylsilane can be used as a component in the synthesis of novel materials with specific properties, such as improved conductivity or stability. Its unique structure and reactivity make it a promising candidate for the development of advanced materials.

Upstream product

• 3141-27-3 2,5-dibromothiophen 
• 10112-09-1 chloromethylsilane 
• 1003-09-4 2-bromothiophene 
• 75-77-4 chloro-trimethyl-silane 
• 17906-71-7 2,5-bis(trimethylsilyl)thiophene 
• 57204-85-0 benzeneseleninyl chloride 
• 19162-80-2 5-bromo-[2]thienyl lithium 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 18246-23-6 5-(trimethylsilyl)thiophene-2-carboxylic acid 
• 1003-09-4 2-bromothiophene 
• 138983-68-3 2-(trimethylsilyl)-5-thienyl boronic acid 
• 18245-28-8 2-(trimethylsilyl)thiophene 
• 13960-01-5 5-(trimethylsilyl)thiophene-2-carbaldehyde 
• 77998-61-9 (4-bromo-thiophen-2-yl)trimethylsilane 
• 207742-50-5 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene 
• 1217503-07-5 (5,5'-(2,5-dibromo-1,4-phenylene)bis(4-bromothiophene-5,2-diyl))bis(trimethylsilane) 
• 1248347-39-8 C₁₃H₂₂BBrO₂SSi 
• 1223560-05-1 2,6-bis(trimethylsilyl)-4-(3,4,5-tris(dodecyloxy)phenyl)-4H-dithieno[3,2-b:2’,3’-d]pyrrole 
• 942070-36-2 trimethyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)silane 

Relevant articles and documents

Macrocyclic Oligothiophene with Stereogenic [2.2]Paracyclophane Scaffolds: Chiroptical Properties from π-Transannular Interactions

The enantiomers of a new cyclic oligothiophene, bridged by two pseudo-ortho[2.2]paracyclophanes, were synthesized as a new class of the chiral π-conjugated system. Single-crystal X-ray diffraction analysis revealed a twisted structure for these oligothiophenes induced by a torsion of the cyclophane moieties. The embedding oligothiophenes into the inherent planar chirality provided a significant enhancement in circular dichroism (CD) spectra thanks to the large magnetic/electric transition dipole moments. In the dicationic state, an intramolecular π dimer was formed due to the strong interactions of the oligothiophenes. We further recorded unprecedented wide ranges of CD spectra in 250–1800 nm region. The transitions are reasonably described by the exciton coupling of the oligothiophenes.

Deprotonative C-H silylation of functionalized arenes and heteroarenes using trifluoromethyltrialkylsilane with fluoride

A highly selective C-H silylation reaction of functionalized arenes and heteroarenes was developed using Ruppert-Prakash reagent (TMSCF3) activated by alkali metal fluoride. TMSCF3 is considered to play dual roles as a precursor of a mild base and also as a silicon electrophile. The silylation is compatible with sensitive functional groups such as halogen and nitro groups.

COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (HETEROARYLENE SPACER MOIETY)

The inventions disclosed and described herein relate to new and efficient generic methods for making a wide variety of compounds having HAr - Z - Har tricyclic cores, wherein HAr is an optionally substituted five or six membered heteroaryl ring, and Hal is a halogen, and Z is a bridging radical, such as S, Sc, NR5, C(O), C(O)C(O), Si(R5)2, SO, S02, PR5, BR5, C(R5)2 or P(O)Rs and both HAr are covalently bound to one another. The synthetic methods employ a "Base-Catalyzed Halogen Dance" reaction to prepare a metallated compound comprising a five or six membered heteroaryl ring comprising a halogen atom, and then oxidatively coupling the reactive intermediate compound. The compounds of Formula (II) and/or oligomer or polymers comprising repeat units having Formula (II) can be useful for making semi-conducting materials, and/or electronic devices comprising those materials. Acyl compounds can be prepared. Heteroarylene substituents can be used. The core tricyclic core can be coupled to itself. The Z group also can be strong electron-withdrawing groups such as C=C(CN)2 or [C=C(CN)212. Organic electronic devices can be made including field-effect transistors. Formula (II).