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632961

Sigma-Aldrich

5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester

97%

Synonyme(s) :

2-(5′-Hexyl-2,2′-bithien-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-[5′-hexyl-2,2′-bithien-5-yl]-1,3,2-dioxaborolane, 5′-N-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5′-N-hexyl-2,2′-bithiophene, 5-Hexyl-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene

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About This Item

Formule empirique (notation de Hill):
C20H29BO2S2
Numéro CAS:
579503-59-6
Poids moléculaire :
376.38
Numéro MDL:
MFCD05664380
Code UNSPSC :
12352103
ID de substance PubChem :
24882530
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

36-40 °C (lit.)

Chaîne SMILES 

CCCCCCc1ccc(s1)-c2ccc(s2)B3OC(C)(C)C(C)(C)O3

InChI

1S/C20H29BO2S2/c1-6-7-8-9-10-15-11-12-16(24-15)17-13-14-18(25-17)21-22-19(2,3)20(4,5)23-21/h11-14H,6-10H2,1-5H3

Clé InChI

XTTRNSNHDCYSEL-UHFFFAOYSA-N

Catégories apparentées

Application

Reagent use for
  • Suzuki-Miyaura cross-coupling reactions and shape-shifting in contorted dibenzotetrathienocoronenes
  • Oligothiophene self-assembly induction into fibers with tunable shape and function
  • Stille coupling and p-conjugated packing structure and hole mobility of bithiophene-bithiazole copolymers with alkyl-thiophene side chains

Reagent used in Preparation of
  • Solution-processed ambipolar field-effect transistor
  • Light harvesting small molecules for use in solution-processed small molecule bulk heterojunction solar cell devices
  • Light-emitting diode (OLED) materials
  • Unsymmetric substituted benzothiadiazole-containing vinyl monomers for RAFT polymerization
  • Pd-catalyzed condensations and synthesis of isoindigo-based oligothiophenes for molecuar bulk heterojunction solar cells
  • Thiophene-benzothiadiazole based donor-acceptor-donor materials

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

A modular molecular framework for utility in small-molecule solution-processed organic photovoltaic devices
Welch, G. C.; et al.
Journal of Materials Chemistry, 21, 12700-12709 (2011)
Bithiophene-bithiazole alternating copolymers with thiophene side chains: Synthesis by organometallic polycondensation and chemical properties of the copolymers
Yamamoto, T.; et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49, 1508-1512 (2011)
Solution-Processed Ambipolar Field-Effect Transistor Based on Diketopyrrolopyrrole Functionalized with Benzothiadiazole
Zhang, Y.; et al.
Advances in Functional Materials, 22, 97-105 (2012)
Benzothiadiazole-Containing Pendant Polymers Prepared by RAFT and Their Electro-Optical Properties
Haussler, M.; et al.
Macromolecules, 43, 7101-7110 (2010)
Francesca Di Maria et al.
Journal of the American Chemical Society, 133(22), 8654-8661 (2011-04-30)
Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur
Afficher tous les articles scientifiques apparentés

Articles

Synthetic Strategy for Large Scale Production of Oligothiophenes

Oligothiophenes are important organic electronic materials which can be produced using synthetic intermediates and Suzuki coupling.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

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