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595314

Sigma-Aldrich

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol

95%

Synonym(e):

1-Methyl-4-pyrazolboronsäure-pinakolester, 1-Methylpyrazol-4-borsäurepinacolester

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About This Item

Empirische Formel (Hill-System):
C10H17BN2O2
CAS-Nummer:
761446-44-0
Molekulargewicht:
208.07
MDL-Nummer:
MFCD03789259
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24881568
NACRES:
NA.22

Assay

95%

Form

solid

mp (Schmelzpunkt)

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

InChIKey

UCNGGGYMLHAMJG-UHFFFAOYSA-N

Verwandte Kategorien

Anwendung

Stable alternative to the boronic acid for Suzuki-Miyaura palladium-catalyzed cross-coupling
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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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)
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)
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
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Artikel

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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