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632961

Sigma-Aldrich

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

97%

Synonym(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

Empirical Formula (Hill Notation):
C20H29BO2S2
CAS Number:
Molecular Weight:
376.38
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

36-40 °C (lit.)

SMILES string

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

InChI key

XTTRNSNHDCYSEL-UHFFFAOYSA-N

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and light-emitting properties of solution-processable oligothiophene derivatives containing triazole moiety
Kim, B.; et al.
Materials Science Forum, 663-665 (2011)
Shape-shifting in contorted dibenzotetrathienocoronenes
Chiu, C-Y.; et al.
Chemical Science, 2, 1480-1486 (2011)
Synthesis, characterization and comparative study of thiophene-benzothiadiazole based donor-acceptor-donor (D-A-D) materials
Sonar, P.; et al.
Journal of Materials Chemistry, 19, 3228-3237 (2009)
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)
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)

Articles

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

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

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

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

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