715565
Benzo[c][1,2,5]thiadiazol-5-ylboronic acid pinacol ester
97%
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About This Item
Empirical Formula (Hill Notation):
C12H15BN2O2S
CAS Number:
Molecular Weight:
262.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
assay
97%
form
solid
mp
81-86 °C
storage temp.
2-8°C
SMILES string
CC1(C)OB(OC1(C)C)c2ccc3nsnc3c2
InChI
1S/C12H15BN2O2S/c1-11(2)12(3,4)17-13(16-11)8-5-6-9-10(7-8)15-18-14-9/h5-7H,1-4H3
InChI key
KISHNZJGTMYYKH-UHFFFAOYSA-N
Application
Benzo[c][1,2,5]thiadiazol-5-ylboronic acid pinacol ester can be used as a reactant:
- To synthesize 5-methylbenzo[c][1,2,5]thiadiazole by methylation reaction with methyl iodide using palladium catalyst.
- In the Miyaura borylation and Suzuki coupling reactions.
- To prepare benzothiadiazole derivatives as potent PFKFB3 kinase inhibitors.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Discovery and Structure-Activity Relationships of N-Aryl 6-Aminoquinoxalines as Potent PFKFB3 Kinase Inhibitors
Boutard N, et al.
ChemMedChem, 14(1), 169-181 (2019)
Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
Haydl AM and Hartwig JF
Organic Letters, 21(5), 1337-1341 (2019)
A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions
Wang X, et al.
Organic Letters, 21(20), 8158-8163 (2019)