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683817 Sigma-Aldrich

2-Formylphenylboronic acid pinacol ester

97%

Synonym: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

  • CAS Number 380151-85-9

  • Empirical Formula (Hill Notation) C13H17BO3

  • Molecular Weight 232.08

  •  MDL number MFCD07363841

  •  PubChem Substance ID 24885782

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Aryl Boronate Esters, Boronate Esters, Boronic Acids and Derivatives, Building Blocks,
Quality Level   100
assay   97%
refractive index   n20/D 1.5143
density   1.0532 g/mL at 25 °C
storage temp.   2-8°C
SMILES string   [H]C(=O)c1ccccc1B2OC(C)(C)C(C)(C)O2
InChI   1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-8-6-5-7-10(11)9-15/h5-9H,1-4H3
InChI key   SLJMPQLPRHIAOM-UHFFFAOYSA-N

Description

Application

2-Formylphenylboronic acid pinacol ester can be used as a starting material to prepare:
• Profluorescent probe applicable for the detection of H2O2 and Fe or Cu ions in living cells.
• Boronic acid pinacol ester derived nickel porphyrin, which is used to synthesize molecular spin switches and electron transfer dyads.
• Fluorescein hydrizido 2-imidophenylboronic ester, a fluorescent sensor prochelator applicable in the detection of copper ions.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
230.0 °F
Flash Point(C) 
> 110 °C

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Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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