3-Acrylamidophenylboronic Acid (contains varying amounts of Anhydride) - ≥97% , CAS No.99349-68-5

CAS: 99349-68-5 Cat. No.: A188951 Peso molecular: 190.99 Número EC: 690-696-8

GRADE & PURITY ≥97%

Synonyms

A846009 | AC-30997 | [3-(prop-2-enamido)phenyl]boronic acid | SCHEMBL235432 | 3-Acrylamidobenzeneboronic Acid | DTXSID50438076 | Phenylboronate acrylamide | BL009552 | SY066256 | AKOS006291555 | AKOS003632579 | FT-0685348 | 3-Acrylamidophenylboronic acid

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

3-Acrylamidophenylboronic acid (AAPBA) is a monomeric compound of boronic acid. The boronic acid group (-B(OH)₂) can form reversible covalent bonds with certain molecules such as diols or sugars. This unique property can be used in the design of molecular sensors to detect and quantify specific types of analytes, such as sugars and biomolecules. The hydrophilicity of the amide group makes it more suitable for drug delivery applications. It can also be used as a synthetic building block to synthesize boronic acid polymers or copolymers for use in biomedical engineering and glucose monitoring biosensors.
Application
3-Acrylamidophenylboronic acid can be used:
As a monomer to synthesize methacrylic acid-3-acrylamidophenylboronic acid copolymer (PMAA-co-AAPBA), which is used as a supramolecular receptor for biosensors. AAPBA helps to enhance the water solubility and binding affinity of the copolymer. This copolymer is used for carbohydrate sensing in aqueous solution.
As a monomer to prepare poly (3-acrylamidophenylboronic acid-b-diethylene glycol dimethacrylate) to make glucose-sensitive nanoparticles for insulin delivery. The specific binding of AAPBA to the diol in the glucose molecule can induce glucose response to the block copolymer.
As a monomer and cross-linker to synthesize self-healing composite hydrogels for tissue engineering and drug delivery systems. This gel can mimic the properties of natural tissues and provide an environment suitable for cell growth. AAPBA polymerizes with acrylamide and acts on the (HPG) cis-diol group of hydroxypropyl guar guar to form a hydrogel with good mechanical strength and rapid self-healing properties.

Specifications

Sinónimos

A846009 | AC-30997 | [3-(prop-2-enamido)phenyl]boronic acid | SCHEMBL235432 | 3-Acrylamidobenzeneboronic Acid | DTXSID50438076 | Phenylboronate acrylamide | BL009552 | SY066256 | AKOS006291555 | AKOS003632579 | FT-0685348 | 3-Acrylamidophenylboronic acid

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 504765393
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765393
• Sonrisas canónicas: B(C1=CC(=CC=C1)NC(=O)C=C)(O)O
• IUPAC Name: [3-(prop-2-enoylamino)phenyl]boronic acid
• InChIKey: ULVXDHIJOKEBMW-UHFFFAOYSA-N
• 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)
• Isómeros SMILES: B(C1=CC(=CC=C1)NC(=O)C=C)(O)O
• Peso molecular: 190.99
• Reaxy-Rn: 9908929
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9908929&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Anilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Anilides
• Alternative Parents: N-arylamides Acrylic acids and derivatives Secondary carboxylic acid amides Boronic acids Organic metalloid salts Organometalloid compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Anilide - N-arylamide - Acrylic acid or derivatives - Boronic acid derivative - Boronic acid - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organic metalloid salt - Organic nitrogen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic metalloid moeity - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Punto de fusión (°C): 129-146°C
• Peso molecular: 190.990 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 191.075 Da
• Monoisotopic Mass: 191.075 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 220.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

Referencias

1. Shulan Jiang, Li Xia, Hao Ma, Tingting Yang, Linmao Qian.  (2023)  pH and temperature dual-responsive hydrogel actuator with bidirectional bending behavior and ultra large bending angle.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2023.112296]

2. Li Luolin, Yu Zheng, Liu Jianfeng, Yang Manyi, Shi Gongpu, Feng Ziqi, Luo Wei, Ma Huiru, Guan Jianguo, Mou Fangzhi.  (2023)  Swarming Responsive Photonic Nanorobots for Motile-Targeting Microenvironmental Mapping and Mapping-Guided Photothermal Treatment.  Nano-Micro Letters,  15  (1): (1-19).  [PMID:37247162] [10.1007/s40820-023-01095-5]

3. Yangjie Li, Site Luo, Yongqiang Gui, Xin Wang, Ziyuan Tian, Haihu Yu.  (2023)  Difunctional Hydrogel Optical Fiber Fluorescence Sensor for Continuous and Simultaneous Monitoring of Glucose and pH.  Biosensors-Basel,  13  (2): (287).  [PMID:36832053] [10.3390/bios13020287]

4. Wenhua Yi, Luo Hai, Yuze Luo, Junqin Li, Ke Yang, Lidan He, Shidong Yang, Le Deng, Dinggeng He.  (2023)  A highly stretchable, adhesive and absorbent hybrid hydrogel dressing for photothermal/chemodynamic antibacterial therapy.  NEW JOURNAL OF CHEMISTRY,  47  (10): (5011-5020).  [PMID:] [10.1039/D2NJ06100G]

5. Shulan Jiang, Li Xia.  (2022)  Bioinspired High-Performance Bilayer, pH-Responsive Hydrogel with Superior Adhesive Property.  Polymers,  14  (20): (4425).  [PMID:36298003] [10.3390/polym14204425]

6. Xiaomei Dai, Jifang Ma, Qiang Zhang, Qingqing Xu, Lele Yang, Feng Gao.  (2021)  Simultaneous inhibition of planktonic and biofilm bacteria by self-adapting semiconducting polymer dots.  Journal of Materials Chemistry B,  9  (33): (6658-6667).  [PMID:34378630] [10.1039/D1TB01070K]

7. Yulong Lan, Yao Wang, Xiaoliang Qi, Erya Cai, Yajing Xiang, XinXin Ge, Hangbin Xu, Xiaojing Chen, Ying Li, Yizuo Shi, Jianliang Shen, Zhiyong Liao.  (2024)  A modified hyaluronic acid hydrogel with strong bacterial capture and killing capabilities for drug-resistant bacteria-infected diabetic wound healing.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39233168] [10.1016/j.ijbiomac.2024.135301]

8. Dunyi Xiao, Huiru Ma, Wei Luo, Jianguo Guan.  (2024)  Agarose-Based Hydrogel Film with Embedded Oriented Photonic Nanochains for Sensing pH.  Polymers,  16  (11): (1530).  [PMID:38891476] [10.3390/polym16111530]

9. Gongpu Shi, Luying Si, Jinyang Cai, Hao Jiang, Yun Liu, Wei Luo, Huiru Ma, Jianguo Guan.  (2024)  Photonic Nanochains for Continuous Glucose Monitoring in Physiological Environment.  Nanomaterials,  14  (11): (964).  [PMID:38869588] [10.3390/nano14110964]

10. Hu Xu, Xin Chen, Yujuan Jia, Xinran Gao, Shuaihang Guo, Dongxu Jia, Yanxia Zhang, Qian Yu.  (2025)  A trifunctional coating for biofilm prevention: integrating antifouling, photothermal killing, and quorum sensing interference.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40795591] [10.1016/j.jcis.2025.138628]

11. Na Su, Hongxiang Ou, Shucheng Liu, Fang Zhu, Honglai Xue, Xuan Zhang.  (2025)  Covalent organic frameworks-based microspheres with precisely designed recognition sites for selective adsorption of luteolin.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2025.135370]

12. Zixiang Wang, Xueyang Yin, Chenyang Zhuang, Kang Wu, Huiren Wang, Zhengzhong Shao, Bo Tian, Hong Lin.  (2024)  Injectable Regenerated Silk Fibroin Micro/Nanosphere with Enhanced Permeability and Stability for Osteoarthritis Therapy.  Small,      [PMID:39101301] [10.1002/smll.202405049]

13. Yingjuan Zhou, Jiaxin Yang, Yan Li, Xin Shu, Yucen Cai, Ping Xu, Wenyan Huang, Zhangyou Yang, Rong Li.  (2024)  Multifunctional nanocomposites mediated novel hydrogel for diabetic wound repair.  Journal of Materials Chemistry B,      [PMID:38502068] [10.1039/D3TB02283H]

14. Xiaoliang Qi, Yulong Lan, Jing Chen, Yajing Xiang, Yingying Wang, Liting Jiang, Yujie Dong, Jiaxin Li, Zhiyong Liao, Zhangping Li, Jianliang Shen.  (2025)  An Endogenous Adenosine Triphosphate-Activated Hydrogel Prodrug System for Healing Multidrug-Resistant Bacteria Infected Diabetic Foot Ulcers.  Advanced Healthcare Materials,      [PMID:40492903] [10.1002/adhm.202500688]

15. Yongqing Zhang, Xiaolong Shang, Jiaqi Guo, Ling Ao, Caihong Shen, Miao Liu, Feng Lin, Wenxian Li, Liqiang Zhang, Baoguo Sun, Wei Dong, Xiaotao Sun, Yanfei Xiong, Songtao Wang, Bo Deng.  (2025)  A computationally driven screening-construction-mechanism strategy of magnetic molecularly imprinted polymers for aliphatic aldehydes detection.  FOOD CHEMISTRY,      [PMID:41213261] [10.1016/j.foodchem.2025.146974]

16. Chunhui Li, Maohang Huang, Huan Yu, Qing Yang, Lijing Hao, Yunhua Chen.  (2025)  pH- and Temperature-Responsive Nanogel Adhesive for Tunable Interfacial Bonding of Hydrogel Materials.  MACROMOLECULAR RAPID COMMUNICATIONS,      [PMID:41401353] [10.1002/marc.202500861]