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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

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

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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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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