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720828

Sigma-Aldrich

Indazole-6-boronic acid

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About This Item

Empirical Formula (Hill Notation):
C7H7BN2O2
CAS Number:
885068-10-0
Molecular Weight:
161.95
MDL number:
MFCD04972419
UNSPSC Code:
12352103
PubChem Substance ID:
329763753
NACRES:
NA.22

form

solid

mp

112-117 °C

storage temp.

2-8°C

SMILES string

OB(O)c1ccc2cn[nH]c2c1

InChI

1S/C7H7BN2O2/c11-8(12)6-2-1-5-4-9-10-7(5)3-6/h1-4,11-12H,(H,9,10)

InChI key

ZKNLCHWRWRYPGG-UHFFFAOYSA-N

Application

Indazole-6-boronic acid can be used as a reactant:
  • In Suzuki-Miyaura coupling reaction to synthesize indazole derivatives via C-C bond formation by reacting with different aryl halides.
  • To synthesize indazole substituted purines and pyrrolo[2,3-d]pyrimidines as potential kinase inhibitors.

Reactant for preparation of:
  • Bicyclic hydroxyphenylmethanone derivatives as hydroxysteroid dehydrogenase inhibitors
  • Bisphosphonate inhibitors of human farnesyl pyrophosphate synthase
  • Indazolyl benzoimidazoles as PKC-ζ inhibitors
  • Pyrazolopyrimidinamine derivatives and their tyrosine and phosphinositide kinase inhibitory activity

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells
Lin Y-S, et al.
Journal of medicinal chemistry, 55(7), 3201-3215 (2012)
Design, synthesis, and preclinical evaluation of fused pyrimidine-based hydroxamates for the treatment of hepatocellular carcinoma
Chen D, et al.
Journal of Medicinal Chemistry, 61(4), 1552-1575 (2018)

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