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Merck

771465

Sigma-Aldrich

3-(Acrylamido)phenylboronic acid

98%

Synonim(y):

3-(Propenamido)phenylboronic acid, N-Acryloyl-3-aminophenylboronic acid, Boronic acid acrylamide, Phenylboronate acrylamide

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About This Item

Wzór empiryczny (zapis Hilla):
C9H10BNO3
Numer CAS:
Masa cząsteczkowa:
190.99
Numer MDL:
Kod UNSPSC:
12162002
Identyfikator substancji w PubChem:
NACRES:
NA.23

Próba

98%

Formularz

powder

mp

129-146 °C

temp. przechowywania

2-8°C

ciąg SMILES

OB(O)c1cccc(NC(=O)C=C)c1

InChI

1S/C9H10BNO3/c1-2-9(12)11-8-5-3-4-7(6-8)10(13)14/h2-6,13-14H,1H2,(H,11,12)

Klucz InChI

ULVXDHIJOKEBMW-UHFFFAOYSA-N

Opis ogólny

3-(Acrylamido)phenylboronic acid(AAPBA) belongs to the class of boronic acid monomers. The boronic acid group (-B(OH)₂)possesses the unique ability to form reversible covalent bonds with certain molecules, such as diols or sugars. This property allows for the design of molecular sensors for detecting and quantifying specific analytes, including carbohydrates and biomolecules. The acrylamido group provides hydrophilic characteristics, making it more suitable for drug delivery applications. It is also utilized as a building block to synthesize boronic acid-based polymers or copolymers for biomedical engineering, and biosensors for glucose monitoring.

Zastosowanie

3-(Acrylamido)phenylboronic acid can be used as:
  • As a monomer to synthesize poly(methacrylic acid)-co-3-(acrylamido)phenylboronic acid (PMAA-co-AAPBA) copolymer as a supramolecular receptor for biosensor applications. AAPBA helps to enhance the water solubility and binding affinity of the copolymer. This copolymer is utilized for carbohydrate sensing in an aqueous medium.
  • As a monomer to prepare poly(3-Acrylamidophenyl boronic acid-b-diethylene glycol dimethacrylate) for the fabrication of glucose-sensitive nanoparticles for insulin delivery. The specific interactions of AAPBA with the diol moiety present in glucose molecules induce glucose responsiveness into the block copolymer.
  • As a monomer and cross-linker to synthesize self-healing composite hydrogels for tissue engineering and drug delivery systems. They can mimic the properties of natural tissues and provide a suitable environment for cell growth. AAPBA polymerizes with acrylamide and simultaneously interacts with cis-diol of hydroxypropyl guar gum (HPG) to facilitate the formation of hydrogel with good mechanical strength and fast self-healing properties.
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Piktogramy

Exclamation mark

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

Klasyfikacja zagrożeń

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable


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Odwiedź Bibliotekę dokumentów

Kataoka; et al.
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Brassinosteriods (BRs), a group of important phytohormones, have various effects on plant growth and development. However, their physiological functions in plants have not been fully understood to date. Endogenous BRs in plant tissue are extremely low and the elucidation of
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In-line coupling of capillary columns is an effective means for achieving miniaturized and automated separation methods. The use of multimodal column designed to allow the direct integration of a sample preparation step to the separation column is one example. Herein
Zayats;Maya; et al.
Tetrahedron, 58, 815-824 (2002)
Xiaoyun Wang et al.
RNA (New York, N.Y.), 24(10), 1305-1313 (2018-07-05)
Eukaryotic transfer RNAs (tRNA) contain on average 13 modifications that perform a wide range of roles in translation and in the generation of tRNA fragments that regulate gene expression. Queuosine (Q) modification occurs in the wobble anticodon position of tRNAs

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