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417130

Sigma-Aldrich

Benzene-1,4-diboronic acid

≥95.0%

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Synonym(s):
p-Phenylenediboronic acid, 1,4-Phenylenebisboronic acid, 1,4-Phenylenediboronic acid, p-Benzenediboronic acid, Benzene-1,4-diboronic acid, NSC 25410
Linear Formula:
C6H4[B(OH)2]2
CAS Number:
4612-26-4
Molecular Weight:
165.75
Beilstein:
2836921
MDL number:
MFCD00236018
PubChem Substance ID:
24866124
NACRES:
NA.22

Assay

≥95.0%

form

powder

mp

>350 °C (lit.)

SMILES string

OB(O)c1ccc(cc1)B(O)O

InChI

1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H

InChI key

BODYVHJTUHHINQ-UHFFFAOYSA-N

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Application

Reagent used for
  • Externally initiated Kumada catalyst-transfer polycondensation
  • Suzuki-Miyaura cross-coupling reactions
  • Energy transfer processes in optoelectronic devices
  • Palladium-catalyzed sequential alkenylation and conjugate addition reactions
  • Scholl cyclizations

Reagent used in Preparation of
  • Crosslinkers and cross-linked core-shell nanoparticles by RAFT polymerization and palladium-catalyzed Suzuki coupling reaction
  • Fluorescence and solution-processable coordination polymers
  • Cyclotricatechylene based porous crystalline material for gas storage
  • Indolizine derivatives as OLEDs
  • Helically p-stacked thiophene-based copolymers with circularly polarized fluorescence
  • Novel organic semiconductors and applications in organic thin-film transistors
  • Highly twisted polycyclic aromatic hydrocarbons with unexptected reactivity

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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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Pd-catalyzed sequential C-C and C-N bond formations for the synthesis of N-heterocycles: exploiting protecting group-directed C-H activation under modified reaction conditions.
Byung Seok Kim et al.
Chemistry, an Asian journal, 6(8), 1952-1957 (2011-03-18)
Anirban Pradhan et al.
Angewandte Chemie (International ed. in English), 50(52), 12582-12585 (2011-11-08)
Let's twist! The Scholl reaction with quinquephenyl derivatives has been shown to have an unexpectedly strong preference for forming twisted, helicene aromatic polycycles, instead of their flat counterparts. This tendency is so strong that it will overcome even severe steric
Nikka Turangan et al.
Nanotechnology, 32(7), 075604-075604 (2020-09-17)
Rigid, freestanding covalent organic framework (COF-1) membranes have been synthesized from 1,4-benzenediboronic acid (BDBA) precursors using two different approaches: room temperature solvent-vapour annealing (SVA) and solvothermal annealing (SA). Characterization of films using Fourier-transform infrared (FTIR) spectroscopy, x-ray diffraction (XRD), and
Jiaxi Wang et al.
Nanoscale, 9(30), 10750-10756 (2017-07-18)
The development of additional functions and applications of covalent organic framework (COF)-derived materials still remains highly desired. In our work, a novel COF-functionalized magnetic graphene biocomposite (MagG@COF-5) was first developed as an ultrasensitive hydrophilic matrix via a facile self-assembly method
Supratim Basak et al.
The Journal of organic chemistry, 77(7), 3620-3626 (2012-03-16)
This paper presents a 10-step synthetic route for the preparation of a series of new back-to-back coupled 2,6-bis(pyrazol-1-yl)pyridine (bpp) ligands (L0-L3) decorated with tetraoctyl chains. Ligand L1 self-assembles with Zn(2+) ion to form a highly soluble metallo-supramolecular polymer 1 with
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