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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

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

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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ACS Symp. Ser., 642, 194-205 (1996)
Jiajia Tan et al.
Biomaterials, 178, 608-619 (2018-04-02)
Inflammation serves as a natural defense mechanism to protect living organisms from infectious diseases. Nonsteroidal anti-inflammatory drugs (NSAIDs) can help relieve inflammatory reactions and are clinically used to treat pain, fever, and inflammation, whereas long-term use of NSAIDs may lead
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)
Regioselective Arylation and Alkynylation of 2,3-Dibromo-1H-inden-1-one by Suzuki-Miyaura and Sonogashira Cross-Coupling Reactions
Khera, R. A.; et al.
Helvetica Chimica Acta, 95, 469-482 (2012)
Jonas Sävmarker et al.
Organic letters, 14(9), 2394-2397 (2012-04-19)
A fast and convenient synthesis of arylamidines starting from readily available potassium aryltrifluoroborates and cyanamides is reported. The coupling was achieved by Pd(II)-catalysis in a one step 20 min microwave protocol using Pd(O(2)CCF(3)), 6-methyl-2,2'-bipyridyl, TFA, and MeOH, providing the corresponding
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