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417130

Sigma-Aldrich

Benzene-1,4-diboronic acid

≥95.0%

Synonym(s):

p-Phenylenediboronic acid, 1,4-Phenylenebisboronic acid, 1,4-Phenylenediboronic acid, p-Benzenediboronic acid, Benzene-1,4-diboronic acid, NSC 25410

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About This Item

Linear Formula:
C6H4[B(OH)2]2
CAS Number:
4612-26-4
Molecular Weight:
165.75
Beilstein:
2836921
MDL number:
MFCD00236018
UNSPSC Code:
12352103
PubChem Substance ID:
24866124
NACRES:
NA.22

Quality Level

100

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCN4358
WXBD2749V
MKCL5264
MKCK3520
MKCF7916

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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
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
Teresa T Duncan et al.
ACS applied materials & interfaces, 9(33), 28069-28078 (2017-08-09)
We have developed soft, peelable organogels from 40% hydrolyzed poly(vinyl acetate) (40PVAc) and benzene-1,4-diboronic acid (BDBA). The organic liquids gelated include dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 2-ethoxyethanol, and methanol. The rheology of these soft materials can be tuned by altering the
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
Multifunctional electron-transporting indolizine derivatives for highly efficient blue fluorescence, orange phosphorescence host and two-color based white OLEDs
Wan, J.; et al.
Journal of Materials Chemistry, 22, 4502-4510 (2012)
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