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595314

Sigma-Aldrich

1-Methylpyrazole-4-boronic acid pinacol ester

95%

Synonyme(s) :

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

Formule empirique (notation de Hill):
C10H17BN2O2
Numéro CAS:
761446-44-0
Poids moléculaire :
208.07
Numéro MDL:
MFCD03789259
Code UNSPSC :
12352103
ID de substance PubChem :
24881568
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

95%

Forme

solid

Pf

59-64 °C (lit.)

Chaîne SMILES 

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

Clé InChI

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
SHBK0801
SHBK4288
SHBB2148V
57496MMV
57496MM

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Consulter la Bibliothèque de documents

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
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
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
Direct conversion of pinacol arylboronic esters to aryl triolborates
Li, G.-Q.; et al.
Chemistry Letters (Jpn), 40, 702-704 (2011)
Afficher tous les articles scientifiques apparentés

Articles

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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