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287512

Sigma-Aldrich

3-Aminophenylboronic acid monohydrate

98%

Synonym(s):

3-Aminobenzeneboronic acid

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About This Item

Linear Formula:
H2NC6H4B(OH)2 · H2O
CAS Number:
206658-89-1
Molecular Weight:
154.96
Beilstein:
2936342
MDL number:
MFCD00149554
UNSPSC Code:
12352103
PubChem Substance ID:
24857277
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

93-96 °C (lit.)

SMILES string

[H]O[H].Nc1cccc(c1)B(O)O

InChI

1S/C6H8BNO2.H2O/c8-6-3-1-2-5(4-6)7(9)10;/h1-4,9-10H,8H2;1H2

InChI key

XAEOVQODHLLNKX-UHFFFAOYSA-N

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Application

Reagent used for
  • Suzuki-Miyaura cross-coupling

Reagent used for Preparation of
  • Gram-positive antivirulence drugs and inhibitors of Streptococcus agalactiae Stk1
  • Regioisomer of Zaleplon (a sedative)
  • Amphiphilic random glycopolymer, which self-assemble to form nanoparticles, with potential as a glucose-sensitive matrix
  • Chemomechanical polymer that expands and contracts in blood plasma with high glucose selectivity

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Synthetic studies connected with the preparation of N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a zaleplon regioisomer
Radl, S.; et al.
Heterocycles, 80, 1359-1379 (2010)
Qianqian Guo et al.
Journal of biomaterials science. Polymer edition, 30(10), 815-831 (2019-05-03)
We reported on the fabrication of sugar-responsive nanogels covalently incorporated with 3-acrylamidophenylboronic acid (AAPBA) as glucose-recognizing moiety, 2-(acrylamido)glucopyranose (AGA) as biocompatible moiety, and boron dipyrromethene (BODIPYMA) as fluorescence donor molecule. The p(AAPBA-AGA-BODIPYMA) nanogels were synthesized via reversible addition-fragmentation chain transfer
Jiangying Zhu et al.
Materials science & engineering. C, Materials for biological applications, 117, 111273-111273 (2020-09-14)
In this work, poly(ethylene glycol)-b-poly[3-acrylamidophenylboronic acid-co-styrene] (PEG-b-P(PBA-co-St) has been firstly synthesized for loading of insulin to form insulin-loaded micelles. Insulin-loaded micelles (ILM) and epidermal growth factor (EGF) are further embedded into the composite hydrogels that can be rapidly gelled by
Jing Zhang et al.
Journal of separation science, 40(5), 1107-1114 (2017-01-04)
Novel 3-aminophenylboronic acid functionalized poly(glycidyl methacrylate-co-ethylene dimethacrylate) microspheres were prepared for the solid-phase extraction of glycopeptides/glycoproteins. The adsorption efficiency, maximum adsorption capacity, and specific recognition of the microspheres to glycoprotein were investigated. The results indicated excellent adsorption of glycoproteins by
Gizem Ertürk Bergdahl et al.
Applied biochemistry and biotechnology, 189(2), 374-383 (2019-04-26)
A capacitive sensor was developed to analyze the presence and enzymatic activity of a model protease from standard solutions by following the degradation of the substrate in real time. The enzyme was chosen based on its specific digestion of the
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