Skip to Content
Merck
All Photos(2)

Documents

697400

Sigma-Aldrich

3-Hexylthiophene-2-boronic acid pinacol ester

95%

Synonym(s):

2-(3-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3-Hexyl-2-thienylboronic acid

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C16H27BO2S
CAS Number:
850881-09-3
Molecular Weight:
294.26
MDL number:
MFCD11045447
UNSPSC Code:
12352103
PubChem Substance ID:
329761917
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.490-1.499

density

0.983 g/mL at 25 °C

SMILES string

CCCCCCc1ccsc1B2OC(C)(C)C(C)(C)O2

InChI

1S/C16H27BO2S/c1-6-7-8-9-10-13-11-12-20-14(13)17-18-15(2,3)16(4,5)19-17/h11-12H,6-10H2,1-5H3

InChI key

XCXAUPBHQCCWCI-UHFFFAOYSA-N

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling reactions
  • p-type/n-type switching of ambipolar bithiazole-benzothiadiazole-based polymers in solar cells
  • Hierarchical self-assembly of semiconductor functionalized peptide a-helixes and optoelectronic properties

Reagent used in Preparation of
  • Photovoltaic materials, polymers, and thiophene-based compounds with photophysical, electrochemical, and fluorescent properties
  • Polymer solar cells for Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units
  • Dithienothiophene-based dyes for dye-sensitized solar cells

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Photophysical and Electrochemical Properties of Thiophene-Based 2-Arylpyridines
Coluccini, C.; et al.
European Journal of Organic Chemistry, 28, 5587-5598 (2011)
p/n Switching of Ambipolar Bithiazole-Benzothiadiazole-Based Polymers in Photovoltaic Cells
Balan, B.; et al.
Macromolecules, 45, 2709-2719 (2012)
Rohan J Kumar et al.
Journal of the American Chemical Society, 133(22), 8564-8573 (2011-05-17)
To determine the ability of semiconductors templated by α-helical polypeptides to form higher order structures and the charge carrier properties of the supramolecular assemblies, L-lysine was functionalized with a sexithiophene organic semiconductor unit via iterative Suzuki coupling and the click
Preparation, structure, and spectral properties of cyclophanes consisting of oligothiophene units
Tsuge, A.; et al.
Chemistry Letters (Jpn), 37, 870-871 (2008)
Photovoltaic response to structural modifications on a series of conjugated polymers based on 2-aryl-2H-benzotriazoles
Pasker, F. M.; et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49, 5001-5011 (2011)
View All Related Papers

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service