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595314

Sigma-Aldrich

1-Methylpyrazole-4-boronic acid pinacol ester

95%

Sinónimos:

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole, 1-Methyl-4-pyrazoleboronic acid pinacol ester, 2-(1-Methylpyrazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-methylpyrazole

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About This Item

Fórmula empírica (notación de Hill):
C10H17BN2O2
Número de CAS:
761446-44-0
Peso molecular:
208.07
MDL number:
MFCD03789259
UNSPSC Code:
12352103
PubChem Substance ID:
24881568
NACRES:
NA.22

assay

95%

form

solid

mp

59-64 °C (lit.)

SMILES string

Cn1cc(cn1)B2OC(C)(C)C(C)(C)O2

InChI

1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3

InChI key

UCNGGGYMLHAMJG-UHFFFAOYSA-N

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling reactions
  • Transesterification reactions

Reagent used for preparation of
  • Aminothiazoles as γ-secretase modulators
  • Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy
  • Pyridine derivatives as TGF-β1 and activin A signalling inhibitors
  • MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer
Stable alternative to the boronic acid for Suzuki-Miyaura palladium-catalyzed cross-coupling

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Direct conversion of pinacol arylboronic esters to aryl triolborates
Li, G.-Q.; et al.
Chemistry Letters (Jpn), 40, 702-704 (2011)
Brijesh Bhayana et al.
Organic letters, 11(17), 3954-3957 (2009-08-12)
A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids with aryl tosylates and mesylates to be performed
Michael Lainchbury et al.
Journal of medicinal chemistry, 55(22), 10229-10240 (2012-10-23)
Inhibitors of checkpoint kinase 1 (CHK1) are of current interest as potential antitumor agents, but the most advanced inhibitor series reported to date are not orally bioavailable. A novel series of potent and orally bioavailable 3-alkoxyamino-5-(pyridin-2-ylamino)pyrazine-2-carbonitrile CHK1 inhibitors was generated
Rudy Ciayadi et al.
Bioorganic & medicinal chemistry letters, 21(18), 5642-5645 (2011-07-26)
Novel inhibitors of TGF-β1 and activin A signalling based on a 2-aryl-4-(3-(pyridin-2-yl)-1H-pyrazol-4-yl)pyridine pharmacophore have been synthesised. Compounds containing phenyl or aromatic nitrogen heterocycle substituents inhibited both types of signalling with HEK-293T cells in culture, with a selectivity preference for TGF-β1.
Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
Asano, S.; Kamioka, S.; Isobe, Y.
Tetrahedron, 68, 272-279 (2012)
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Artículos

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

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