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Merck
CN

697400

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

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About This Item

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

Key Documents

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Product Name

3-Hexylthiophene-2-boronic acid pinacol ester, 95%

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

SMILES string

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

InChI key

XCXAUPBHQCCWCI-UHFFFAOYSA-N

assay

95%

form

liquid

refractive index

n20/D 1.490-1.499

density

0.983 g/mL at 25 °C

Quality Level

100

Related Categories

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

10 - Combustible liquids

wgk

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM2423
SHBG1509V
SHBC9438V
SHBC3621V
SHBB6939V

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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)
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
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Synthetic Strategy for Large Scale Production of Oligothiophenes

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

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