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595314

Sigma-Aldrich

1-Methylpyrazole-4-boronic acid pinacol ester

95%

Synonym(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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1 G
$69.58
5 G
$197.00
25 G
$954.00

About This Item

Empirical Formula (Hill Notation):
C10H17BN2O2
CAS Number:
761446-44-0
Molecular Weight:
208.07
MDL number:
MFCD03789259
UNSPSC Code:
12352103
PubChem Substance ID:
24881568
NACRES:
NA.22

$69.58

List Price$87.30Save 20%
Web-Only Promotion

Available to ship onMay 01, 2025Details

Request a Bulk Order

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[1][2][3]
  • Transesterification reactions[4]

Reagent used for preparation of
  • Aminothiazoles as γ-secretase modulators[5]
  • Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy[6]
  • Pyridine derivatives as TGF-β1 and activin A signalling inhibitors[7]
  • MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer[8]
Stable alternative to the boronic acid for Suzuki-Miyaura palladium-catalyzed cross-coupling[9]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK0801
SHBK4288
SHBB2148V
57496MMV
57496MM

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Jason D Katz et al.
Journal of medicinal chemistry, 54(12), 4092-4108 (2011-05-26)
c-Met is a transmembrane tyrosine kinase that mediates activation of several signaling pathways implicated in aggressive cancer phenotypes. In recent years, research into this area has highlighted c-Met as an attractive cancer drug target, triggering a number of approaches to
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
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
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
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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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