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632732

Sigma-Aldrich

1-Boc-pyrazole-4-boronic acid pinacol ester

97%

Synonym(s):

1,1-dimethylethyl ester 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-Pyrazole-1-carboxylic acid, 1-tert-Butoxycarbonyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrazole, 1-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole, 1-Boc-4-pyrazoleboronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-Boc-pyrazole, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylic acid tert-butyl ester, tert-Butyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pyrazolecarboxylate, [1-(tert-Butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C14H23BN2O4
Molecular Weight:
294.15
MDL number:
MFCD05663873
UNSPSC Code:
12352103
PubChem Substance ID:
24882509
NACRES:
NA.22

assay

97%

form

solid

mp

82-86 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)n1cc(cn1)B2OC(C)(C)C(C)(C)O2

InChI

1S/C14H23BN2O4/c1-12(2,3)19-11(18)17-9-10(8-16-17)15-20-13(4,5)14(6,7)21-15/h8-9H,1-7H3

InChI key

IPISOFJLWYBCAV-UHFFFAOYSA-N

Application

Reagent used for
  • Suzuki Coupling
  • Copper-catalyzed azidation

Reagent used in Preparation of
  • Selective quinazolinyl-phenol inhibitors of CHK1 as potential antitumors and radioprotectants
  • Stereoselective synthesis of selective Cathepsin inhibitors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK0294
MKBJ7503V
MKBG5798V
MKBD9142V
73596PJ

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Copper(II)-catalyzed conversion of aryl/heteroaryl boronic acids, boronates, and trifluoroborates into the corresponding azides: substrate scope and limitations
K. D. Grimes, et al.,
Synthesis, 9, 1441-1448 (2010)
John J Caldwell et al.
Journal of medicinal chemistry, 54(2), 580-590 (2010-12-29)
Structure-based design was applied to the optimization of a series of 2-(quinazolin-2-yl)phenols to generate potent and selective ATP-competitive inhibitors of the DNA damage response signaling enzyme checkpoint kinase 2 (CHK2). Structure-activity relationships for multiple substituent positions were optimized separately and
Paul A Bethel et al.
Bioorganic & medicinal chemistry letters, 19(16), 4622-4625 (2009-07-21)
A number of molecular recognition features have been exploited in structure-based design of selective Cathepsin inhibitors.

Articles

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

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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

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