Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing

Select a Size

1 G
$87.30
5 G
$197.00
25 G
$954.00

$87.30

Only 14 left in stockDetails
Request a Bulk Order
All Photos(3)

Select a Size

Change View
1 G
$87.30
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

$87.30

Only 14 left in stockDetails
Request a Bulk Order

Quality Level

100

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBK0801
SHBK4288
SHBB2148V
57496MMV
57496MM

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Direct conversion of pinacol arylboronic esters to aryl triolborates
Li, G.-Q.; et al.
Chemistry Letters (Jpn), 40, 702-704 (2011)
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
View All Related Papers

Articles

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service