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542202

Sigma-Aldrich

2-Biphenylboronic acid

≥95%

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About This Item

Linear Formula:
C6H5C6H4B(OH)2
CAS Number:
4688-76-0
Molecular Weight:
198.03
MDL number:
MFCD00136929
UNSPSC Code:
12352103
PubChem Substance ID:
24878589
NACRES:
NA.22

assay

≥95%

mp

167-172 °C (lit.)

functional group

phenyl

SMILES string

OB(O)c1ccccc1-c2ccccc2

InChI

1S/C12H11BO2/c14-13(15)12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,14-15H

InChI key

HYCYKHYFIWHGEX-UHFFFAOYSA-N

Application

Reactant involved in:
  • Suzuki-Miyaura cross-coupling reactions with arylhalides, dibromovinyl precursors, alkenyl tosylates and mesylates, and quinoline carboxylates
  • Intramolecular Friedel-Crafts alkylation for synthesis of chiral tetralins
  • Hydroxylation to phenols
  • Oxidative coupling iwth alkynes
Substrate employed in a palladium-catalyzed cross-coupling with benzylic acetates providing diarylmethanes.

Other Notes

Contains varying amounts of anhydride.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
13296AKV
13296AK
00230PH
09229CH
00126AE

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Ryoichi Kuwano et al.
Chemical communications (Cambridge, England), (47), 5899-5901 (2005-12-01)
Benzylic acetates reacted with arylboronic acids in the presence of a DPEphos-[Pd(eta3-C3H5)Cl]2 catalyst when tert-amyl alcohol was used as a solvent, and the catalytic cross-couplings produced diarylmethanes in high yields (up to 94% isolated yield).
Chuei Wakasugi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(24), 5449-5458 (2020-02-23)
Transition-metal complexes bearing biaryl-2,2'-diyl ligands tend to show intense luminescence. However, difficulties in synthesis have prevented their further functionalization and practical applications. Herein, a series of platinum(II) complexes bearing biaryl-2,2'-diyl ligands, which have never been prepared in air, were synthesized
Dongxue Han et al.
Nature communications, 11(1), 5659-5659 (2020-11-11)
Chiral optical materials based on circularly polarized luminescence (CPL) have emerged rapidly due to their feasible applications in diverse fields of research. However, limited to the small luminescence dissymmetry factor (glum), real application examples have rarely been reported. Here, we

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