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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

Categorías relacionadas

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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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.
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
Direct conversion of pinacol arylboronic esters to aryl triolborates
Li, G.-Q.; et al.
Chemistry Letters (Jpn), 40, 702-704 (2011)
Guopin Xu et al.
Organic letters, 7(21), 4605-4608 (2005-10-08)
[reaction: see text] The synthesis of a series of NHC building blocks that can then be incorporated into more complicated structures by palladium catalysis is reported. This approach is used for the synthesis of three amino acids containing NHC side
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.

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