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Sigma-Aldrich

3-Aminophenylboronic acid

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Synonym(s):
3-Aminobenzeneboronic acid
Empirical Formula (Hill Notation):
C6H8BNO2
CAS Number:
Molecular Weight:
136.94
EC Number:
MDL number:

form

powder or crystals

Quality Level

mp

225 °C

SMILES string

Nc1cccc(c1)B(O)O

InChI

1S/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2

InChI key

JMZFEHDNIAQMNB-UHFFFAOYSA-N

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This Item
A71751287512410705
mp

225 °C

mp

≥300 °C

mp

93-96 °C (lit.)

mp

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

Application

3-Aminophenylboronic acid (3-APBA) can undergo three-component condensation with 3,5-disubstituted salicylaldehyde derivatives and aliphatic alcohols to afford calix-shaped boron complexes. Due to its ability to selectively bind with diol-compounds, 3-APBA can be employed in developing sensors for detecting saccharides and glycosylated biomolecules by immobilizing on a metal substrate via a self-assembled monolayer. This product was previously listed as CDS003827.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Rodtichoti Wannapob et al.
Biosensors & bioelectronics, 26(2), 357-364 (2010-08-31)
Boronic acid that can reversibly bind to diols was used to detect bacteria through its affinity binding reaction with diol-groups on bacterial cell walls. 3-aminophenylboronic acid (3-APBA) was immobilized on a gold electrode via a self-assembled monolayer. The change in
3-Aminophenylboronic acid as building block for the construction of calix- and cage-shaped boron complexes.
Barba V, et al.
Journal of Organometallic Chemistry, 694, 2127-2133 (2009)

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