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595314

Sigma-Aldrich

1-Methylpyrazole-4-boronic acid pinacol ester

95%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C10H17BN2O2
Numero CAS:
761446-44-0
Peso molecolare:
208.07
Numero MDL:
MFCD03789259
Codice UNSPSC:
12352103
ID PubChem:
24881568
NACRES:
NA.22

Saggio

95%

Stato

solid

Punto di fusione

59-64 °C (lit.)

Stringa SMILE

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
UCNGGGYMLHAMJG-UHFFFAOYSA-N

Applicazioni

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
SHBK0801
SHBK4288
SHBB2148V
57496MMV
57496MM

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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.
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
Thomas Lübbers et al.
Bioorganic & medicinal chemistry letters, 21(21), 6554-6558 (2011-09-20)
We herein report the discovery of a new γ-secretase modulator class with an aminothiazole core starting from a HTS hit (3). Synthesis and SAR of this series are discussed. These novel compounds demonstrate moderate to good in vitro potency in
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Articoli

Suzuki–Miyaura Coupling Reagents

This brochure contains a comprehensive selection of boronic acids, boronic acid esters, diboron esters, and transition-metal catalysts useful for the Suzuki–Miyaura coupling reaction

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