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Safety Information

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:
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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

393622-250MG:
393622-BULK:
393622-VAR:
393622-1G:
393622-10G:

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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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