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663816

Sigma-Aldrich

1,4-Benzenediboronic acid bis(pinacol) ester

97%

Synonym(s):

1,4-Benzenediboronic acid dipinacol ester, 1,4-Bis(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, 1,4-Phenylenebis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane), cyclic bis(tetramethylethylene) ester p-Benzenediboronic acid

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About This Item

Empirical Formula (Hill Notation):
C18H28B2O4
CAS Number:
99770-93-1
Molecular Weight:
330.03
MDL number:
MFCD08276852
UNSPSC Code:
12352103
PubChem Substance ID:
24884661
NACRES:
NA.22

Assay

97%

form

solid

mp

241-245 °C

SMILES string

CC1(C)OB(OC1(C)C)c2ccc(cc2)B3OC(C)(C)C(C)(C)O3

InChI

1S/C18H28B2O4/c1-15(2)16(3,4)22-19(21-15)13-9-11-14(12-10-13)20-23-17(5,6)18(7,8)24-20/h9-12H,1-8H3

InChI key

UOJCDDLTVQJPGH-UHFFFAOYSA-N

Related Categories

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling reactions and polymerizations

Reagent used in Prepration of
  • Efficient solar cell photoelectric polymers
  • Field-effect transistors and photovoltaic cells
  • Fluorescent compounds and materials such as Blue OLED devices, Blue Polymeric Light Emitting Diodes, and White LEDs

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH6566
MKBW8502V
MKBR8880V
MKBH3593V
MKBD8034V

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Efficient solar cells based on an easily accessible diketopyrrolopyrrole polymer
Bijleveld, J. C.; et al.
Advanced Materials, 22, 242-246 (2010)
Small band gap copolymers based on furan and diketopyrrolopyrrole for field-effect transistors and photovoltaic cells
Bijleveld, J. C.; et al.
Journal of Materials Chemistry, 21, 1600-1606 (2011)
Preparation of p-conjugated polymer/silica hybrids particle and their application to white light emitting diode
Kubo, M.; et al.
Kobunshi Ronbunshu, 65, 427-432 (2008)
Synthesis, characterization, and crystal structure of [6]cycloparaphenylene.
Jianlong Xia et al.
Angewandte Chemie (International ed. in English), 51(10), 2474-2476 (2012-01-31)
Moussa Saleh et al.
Macromolecular rapid communications, 30(14), 1279-1283 (2009-07-16)
Three polytriphenylene derivatives with phenyl and alkyl groups as side chains have been tested as blue light emitters. The best performance in terms of turn-on voltage and luminance efficiencies was obtained for poly(2-heptyl-3-(4-octylphenyl)-1,4-diphenyl-6,11-triphenylenyl-1,4-benzene) (1), which was additionally blended with an
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Articles

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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