636010
3,5-Dimethylpyrazole-4-boronic acid pinacol ester
97%
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Synonym(s):
3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)-1H-pyrazole, 3,5-Dimethyl-4-pyrazoleboronic acid pinacol ester
Empirical Formula (Hill Notation):
C11H19BN2O2
CAS Number:
Molecular Weight:
222.09
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
solid
mp
163-168 °C (lit.)
SMILES string
Cc1n[nH]c(C)c1B2OC(C)(C)C(C)(C)O2
InChI
1S/C11H19BN2O2/c1-7-9(8(2)14-13-7)12-15-10(3,4)11(5,6)16-12/h1-6H3,(H,13,14)
InChI key
GNUDAJTUCJEBEI-UHFFFAOYSA-N
Related Categories
Application
3,5-Dimethylpyrazole-4-boronic acid pinacol ester can be used:
- To synthesize 9H-pyrimido[4,5-b]indole and aryl-benzimidazole based BET bromodomain and extra terminal (BET) protein inhibitors.
- To prepare naphthalimide based photo-exchangeable photochromic fluorescent molecules.
- As a reactant to develop DNA-encoded chemical libraries by palladium-catalyzed Suzuki coupling reaction with DNA-linked aryl halides.
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Structure-guided discovery of a novel, potent, and orally bioavailable 3, 5-dimethylisoxazole aryl-benzimidazole BET bromodomain inhibitor
Sperandio D, et al.
Bioorganic & Medicinal Chemistry, 27(3), 457-469 (2019)
Development of DNA-compatible suzuki-miyaura reaction in aqueous media
Li J and Huang H
Bioconjugate Chemistry, 29(11), 3841-3846 (2018)
Investigation of Photochromic Fluorescence Features and Synthesis of Diarylethene Type Naphthalimide Compounds
Orhan E and Narin M
Journal of the Turkish Chemical Society Section A: Chemistry, 7(1), 97-106 (2020)
Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9 H-pyrimido [4, 5-b] indol-7-yl)-3, 5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor
Zhao Y, et al.
Journal of medicinal chemistry, 60(9), 3887-3901 (2017)
Articles
Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.
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