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393622

Sigma-Aldrich

p-Tolylboronic acid

97%

Synonym(s):

(p-Methylphenyl)boronic acid, 4-Methylbenzeneboronic acid, 4-Methylphenylboronic acid, 4-Tolueneboronic acid, 4-Tolylboronic acid, p-Tolueneboronic acid, NSC 62870, p-Methylbenzeneboronic acid

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About This Item

Linear Formula:
CH3C6H4B(OH)2
CAS Number:
5720-05-8
Molecular Weight:
135.96
Beilstein/REAXYS Number:
2935970
MDL number:
MFCD00039138
UNSPSC Code:
12352103
PubChem Substance ID:
24864529
NACRES:
NA.22

Quality Level

100

assay

97%

mp

256-263 °C (lit.)

SMILES string

Cc1ccc(cc1)B(O)O

InChI

1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3

InChI key

BIWQNIMLAISTBV-UHFFFAOYSA-N

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Application

Reagent used for
  • Palladium (Pd)-catalyzed direct arylation
  • Direct Palladium(II)-Catalyzed Synthesis
  • Palladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in water
  • Cyclopalladation
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence
  • Ruthenium catalyzed direct arylation
  • Rhodium-catalyzed asymmetric conjugate addition
  • Ligand-free copper-catalyzed cross-coupling reactions
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions
  • Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions

Reagent used in Preparation of
  • Catalysts for Suzuki-Miyaura cross-coupling of aryl bromides
  • Recyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN8873
MKCK6265
MKCD6002
MKCB8179
MKBX9746V

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ACS Symp. Ser., 642, 194-205 (1996)
Daniel P O'Connell et al.
Bioorganic & medicinal chemistry letters, 22(3), 1397-1401 (2012-01-10)
Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The
Carbon-Carbon Bond Formation by Ligand-free Cross-Coupling Reaction Using Palladium Catalyst Supported on Synthetic Adsorbent
Monguchi, Y.; et al.
ChemCatChem, 4, 546-558 (2012)
Palladium nanoparticles immobilized by click ionic copolymers: Efficient and recyclable catalysts for Suzuki-Miyaura cross-coupling reaction in water
Zhang, D.; Zhou, C.; Wang, R.
Catalysis Communications, 22, 83-88 (2012)
Feng Xue et al.
The Journal of organic chemistry, 77(7), 3071-3081 (2012-03-27)
An efficient rhodium/olefin-sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to a variety of nitroalkenes has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be highly effective and are applicable to a broad scope of aryl, alkyl
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