18246-28-1

Usage

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 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 19162-80-2 5-bromo-[2]thienyl lithium 

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

Relevant academic research and scientific papers

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.

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.

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).

COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (ACYL MOIETIES)

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, Se, NR5, C(O), C(O)C(O), Si(R5)2, SO, SO2, PR5, BR5, C(R5)2 or P(O)R5 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 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)2]2. Organic electronic devices can be made including field-effect transistors.

COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (ELECTRON WITHDRAWING GROUPS)

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, SO2, PR5, BR5, C(R5)2 or P(O)R5 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)2]2. Organic electronic devices can be made including field-effect transistors. Formula (II).

COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (COUPLED TRICYCLIC CORE COMPOUNDS)

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 (II) from intermediates (I), 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, NRS, C(O), C(O)C(O), Si(R5)2, SO, S02, PRS, BRS, C(R5)2 or P(O)R5 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 (IT) can be useful for making semi-conducting materials, and/or electronic devices comprising those materials. Acyl compounds can be prepared. Heteroary- lene 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)2]2. Organic electronic devices can be made including field-effect transistors. (Formula I, II)

Synthesis and photovoltaic properties of functional dendritic oligothiophenes

Novel p-type and low bandgap functional dendritic oligothiophenes bearing hole-transporting carbazole as peripheral substituents and an electron-withdrawing dicyanovinyl core group, namely, DCT(n)-DCN, where n = 1 or 2 for solution-processable photovoltaic (PV) applications have been synthesized. With electron-donating carbazole surface-functionalized moieties conjugated with dicyanovinyl core group, the optical bandgap of these functional dendritic oligothiophene thin-films greatly reduces to 1.74 eV with a strong spectral broadening and a high ionization potential at ～5.5 eV as determined by UV photoelectron spectroscopy. The bulk heterojunction PV cells fabricated from these dendrimers blended with PC71BM as an acceptor showed a power conversion efficiency up to 1.64% with an open circuit voltage of (V oc) = 0.93 V in the annealed device. We have demonstrated that the desirable molecular and PV properties of dendritic oligothiophenes can be obtained/tuned by the incorporation of functional group(s) onto peripheral of the dendron and into the core. In addition, these functional dendritic oligothiophenes show superior functional properties even at low dendritic generation as compared to the unsubstituted higher generation dendritic oligothiophenes as a p-type, low-bandgap semiconductor for solution-processable bulk heterojunction PV cells.

Benzobis(silolothiophene)-based low bandgap polymers for efficient polymer solar cells

Two new low bandgap copolymers that contain a thiophene-phenylene-thiophene fused ring in which the linked carbon atoms are replaced by silicon atoms were designed and synthesized. A facile synthetic method was developed to synthesize the benzobis(silolothiophene) donor unit in high yield. 2-Bromothiophene was lithiated by LDA and subsequently quenched with trimethylsilyl chloride, yielding colorless oil. Further lithiation of 2 with LDA and then reaction with 2-isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane afforded 3 in 52% yields. After lithiation of 5 by n-BuLi, cyclization with dichlorodialkylsilane was performed to get the disilole 6 in 76% yields. Low band gap polymers PBSTBT and PBSTDTBT were obtained though a Stille reaction between monomer and 4,7-dibromo-2,1,3-benzothiadiazole or 4,7-bis(2-bromo-5-thienyl)-2,1,3- benzothiadiazole, using Pd(PPh3)4 as catalyst in toluene. The AFM images of the blended films containing both polymer and PC 71BM showed rather smooth morphology with small phase segregation.

METHOD OF MAKING COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING

The inventions disclosed and described herein relate to new and efficient generic methods for making a wide variety of compounds having Formulas (I) and (II) as shown below (Formulas (I) and (II)) wherein HAr is an optionally substituted five or six membered heteroaryl ring, and Hal is a halogen, and Y is a bridging radical, such as S, Se, NR5 C(O), C(O)C(O),Si(R5)2, SO, SO2, PR5, BR5, C(R5)2 or P(O)R5. 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.