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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:
2935970
MDL number:
MFCD00039138
UNSPSC Code:
12352103
PubChem Substance ID:
24864529
NACRES:
NA.22
Pricing and availability is not currently available.

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[1]
  • Direct Palladium(II)-Catalyzed Synthesis[2]
  • Palladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in water[3]
  • Cyclopalladation[4]
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence[5]
  • Ruthenium catalyzed direct arylation[6]
  • Rhodium-catalyzed asymmetric conjugate addition[7]
  • Ligand-free copper-catalyzed cross-coupling reactions[8]
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions[9]
  • Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions[10]

Reagent used in Preparation of
  • Catalysts for Suzuki-Miyaura cross-coupling of aryl bromides[4]
  • Recyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water[11]

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF2973V
MKCS3694
WXBD8292V
WXBD8902V
MKCN8873

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ACS Symp. Ser., 642, 194-205 (1996)
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)
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
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
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
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MIDA-protected boronate esters offer stability, chromatography compatibility, and reactivity in anhydrous cross-coupling conditions.

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Questions

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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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  2. How can I determine the shelf life / expiration / retest date of this product?

    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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