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| | (3-acrylamidophenyl)boronic acid Basic information |
| Product Name: | (3-acrylamidophenyl)boronic acid | | Synonyms: | (M-ACRYLAMIDOPHENYL)BORONIC ACID;3-(Acrylamido)phenylboronic acid, 3-[(Prop-2-enoyl)amino]benzeneboronic acid;3-(Acryloylamino)benzeneboronic acid;3-(AcrylaMido)phenylboronic acid 98%;3-(Propenamido)phenylboronic acid;Boronic acid acrylamide;N-Acryloyl-3-aminophenylboronic acid;Phenylboronate acrylamide | | CAS: | 99349-68-5 | | MF: | C9H10BNO3 | | MW: | 190.99 | | EINECS: | | | Product Categories: | Aryl;Organoborons | | Mol File: | 99349-68-5.mol |  |
| | (3-acrylamidophenyl)boronic acid Chemical Properties |
| Melting point | 129-146°C | | density | 1.22±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | 8.05±0.10(Predicted) | | form | powder to crystal | | color | White to Amber | | 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) | | InChIKey | ULVXDHIJOKEBMW-UHFFFAOYSA-N | | SMILES | OB(O)c1cccc(NC(=O)C=C)c1 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | HS Code | 2931900090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral |
| | (3-acrylamidophenyl)boronic acid Usage And Synthesis |
| Uses | suzuki reaction | | Uses | This acrylamide monomer contains a glucose sensitive boronic acid commonly used for intelligent polymers solutions and gels;for drug delivery systems;sensors;actuator systems;and bioreactors. | | Synthesis | General procedure for the synthesis of 3-acrylamidophenylboronic acid from 3-aminophenylboronic acid and acryloyl chloride: 3-aminophenylboronic acid (0.566 g, 3.65 mmol) and Na2CO3 (0.67 g, 80.3 mmol) were added to 20 mL of a 1:1 (v/v) solvent mixture of tetrahydrofuran and water and the mixture was cooled to 0 °C. Acryloyl chloride (960 mg, 8.06 mmol) was slowly added dropwise under stirring conditions. After the dropwise addition, the mixture was allowed to warm up naturally to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, 10 mL of water was added to terminate the reaction, followed by extraction of the reaction mixture with ethyl acetate (20 mL x 3). The organic phases were combined, washed with saturated NaCl solution (10 mL) and finally the organic layer was dried with anhydrous Na2SO4. After concentrating the organic layer, it was purified by column chromatography to give the light yellow solid product 3-acrylamidophenylboronic acid (0.32 g, 40.1% yield). | | References | [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4636 - 4656
[2] Soft Matter, 2014, vol. 10, # 6, p. 911 - 920
[3] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19832 - 19838
[4] Patent: CN104945411, 2018, B. Location in patent: Paragraph 0077; 0078; 0079
[5] New Journal of Chemistry, 2012, vol. 36, # 2, p. 438 - 451 |
| | (3-acrylamidophenyl)boronic acid Preparation Products And Raw materials |
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