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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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5 G
€120.00
25 G
€287.00

€120.00


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5 G
€120.00
25 G
€287.00

About This Item

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

€120.00


Please contact Customer Service for Availability

Request a Bulk Order

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[1]
  • Suzuki-Miyaura cross-coupling reactions[2]
  • Energy transfer processes in optoelectronic devices[3]
  • Palladium-catalyzed sequential alkenylation and conjugate addition reactions[4]
  • Scholl cyclizations[5]

Reagent used in Preparation of
  • Crosslinkers and cross-linked core-shell nanoparticles by RAFT polymerization and palladium-catalyzed Suzuki coupling reaction[6]
  • Fluorescence and solution-processable coordination polymers[7]
  • Cyclotricatechylene based porous crystalline material for gas storage[8]
  • Indolizine derivatives as OLEDs[2]
  • Helically p-stacked thiophene-based copolymers with circularly polarized fluorescence[9]
  • Novel organic semiconductors and applications in organic thin-film transistors[10]
  • Highly twisted polycyclic aromatic hydrocarbons with unexptected reactivity[5]

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

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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Multifunctional electron-transporting indolizine derivatives for highly efficient blue fluorescence, orange phosphorescence host and two-color based white OLEDs
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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
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)
Cyclotricatechylene based porous crystalline material: Synthesis and applications in gas storage
Yu, J-T.; et al.
Journal of Materials Chemistry, 22, 5369-5373 (2012)

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Professor Aran discusses engineering graphene-based materials through careful functionalization, enabling diverse applications.

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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