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Sigma-Aldrich

3-(Acrylamido)phenylboronic acid

3-(Acrylamido)phenylboronic acid
1 of 1 reviewers received a sample product or took part in a promotion

98%

Synonym(s):

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

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$151.00

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About This Item

Empirical Formula (Hill Notation):
C9H10BNO3
CAS Number:
99349-68-5
Molecular Weight:
190.99
MDL number:
MFCD09025755
UNSPSC Code:
12162002
PubChem Substance ID:
329767498
NACRES:
NA.23

$151.00

Available to ship onApril 22, 2025Details

Request a Bulk Order

Quality Level

100

assay

98%

form

powder

mp

129-146 °C

storage temp.

2-8°C

SMILES string

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)

InChI key

ULVXDHIJOKEBMW-UHFFFAOYSA-N

Related Categories

General description

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.[1] [2] [3]

Application

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.[1]
  • 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.[2]
  • 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.[4]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2514
MKCT8262
MKCQ8747
MKCN8905
MKCM4208

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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
Jun Ding et al.
Plant methods, 9, 13-13 (2013-04-19)
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
Kataoka; et al.
Macromolecules, 27, 1061-1062 (1994)
Qian-Chun Zhang et al.
Molecules (Basel, Switzerland), 25(4) (2020-02-23)
In this study, a novel monolithic capillary column based on a NH2-MIL-53(Al) metal-organic framework (MOF) incorporated in poly (3-acrylamidophenylboronic acid/methacrylic acid-co-ethylene glycol dimethacrylate) (poly (AAPBA/MAA-co-EGDMA)) was prepared using an in situ polymerization method. The characteristics of the MOF-polymer monolithic column
Mohamed Elsherif et al.
ACS nano, 12(6), 5452-5462 (2018-05-12)
Low-cost, robust, and reusable continuous glucose monitoring systems that can provide quantitative measurements at point-of-care settings is an unmet medical need. Optical glucose sensors require complex and time-consuming fabrication processes, and their readouts are not practical for quantitative analyses. Here
View All Related Papers
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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Reviews

1 of 1 reviewers received a sample product or took part in a promotion

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  1. Newcastle, UK
    • Review 1
    • Votes 2
    5 out of 5 stars.

    Good quality and solubility

    Good quality and solubility. The latest batch is really easier to disolve in polyacrylamide-urea mix to prepare gels for electrophoresis. Previously we had problems with bigger pieces which were hard to solubilize but now it is fine powder, easy to use.

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