Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

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

Quality Level

100

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBM2423
SHBG1509V
SHBC9438V
SHBC3621V
SHBB6939V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

p/n Switching of Ambipolar Bithiazole-Benzothiadiazole-Based Polymers in Photovoltaic Cells
Balan, B.; et al.
Macromolecules, 45, 2709-2719 (2012)
Photophysical and Electrochemical Properties of Thiophene-Based 2-Arylpyridines
Coluccini, C.; et al.
European Journal of Organic Chemistry, 28, 5587-5598 (2011)
Tae-Hyuk Kwon et al.
The Journal of organic chemistry, 76(10), 4088-4093 (2011-04-14)
A one-pot synthesis of 2,6-dibromodithieno[3,2-b;2',3'-d]thiophene (dibromo-DTT, 4) was developed. A key step was bromodecarboxylation of DTT-2,6-dicarboxylic acid, obtained by saponification of the diester 1. The donor-acceptor dye DAHTDTT (13), based on a central 2,6-bis[2'-(3'-hexylthienyl)]dithieno[3,2-b;2',3'-d]thiophene core (9), was prepared and incorporated
Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units: Synthesis, characterization and application in polymer solar cells
Operamolla, A.; et al.
Solar Energy Mat. and Solar Cells, 95, 3490-3503 (2011)
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
View All Related Papers

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