Bis[2-(methacryloyloxy)ethyl] phosphate , CAS No.32435-46-4

CAS: 32435-46-4 Cat. No.: B487024 Molecular Weight: 322.25 EC Number: 251-040-2

Synonyms

Bis(methacryloyloxyethyl) hydrogen phosphate

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Bis[2-(methacryloyloxy)ethyl] phosphate (BMEP) is a hydrophilic monomer with two polymerizable methacrylate groups and a centrally placed phosphate group. In presence of an acid, it can undergo spontaneous polymerization with a high degree of conversion. It is widely used as a precursor in the synthesis of poly (BMEP), dental resins, hydrogels, and fire-retardant polymer composites.

Application：

Bis[2-(methacryloyloxy)ethyl] phosphate (BMEP) can be used:
As a bifunctional crosslinker to synthesize superabsorbent polymers (SAPs) via free radical polymerization. These SAPs can be used for agricultural applications.
To prepare self-etching primer formulations for enamel and dentine. Primers with BMEP exhibit good wetting, etching, and penetration in both dentine and enamel.
As a precursor to synthesize fire retardant nanocomposites via suspension polymerization.

Specifications

Synonyms

Bis(methacryloyloxyethyl) hydrogen phosphate

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC(=C)C(=O)OCCOP(=O)(O)OCCOC(=O)C(=C)C
• IUPAC Name: 2-[hydroxy-[2-(2-methylprop-2-enoyloxy)ethoxy]phosphoryl]oxyethyl 2-methylprop-2-enoate
• InChIKey: NXBXJOWBDCQIHF-UHFFFAOYSA-N
• INCHI: 1S/C12H19O8P/c1-9(2)11(13)17-5-7-19-21(15,16)20-8-6-18-12(14)10(3)4/h1,3,5-8H2,2,4H3,(H,15,16)
• Isomeric SMILES: CC(=C)C(=O)OCCOP(=O)(O)OCCOC(=O)C(=C)C
• Molecular Weight: 322.25
• Reaxy-Rn: 8570304
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8570304&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic phosphoric acids and derivatives
      • Subclass Phosphate esters
        • Level5 Alkyl phosphates
          • Level6 Dialkyl phosphates

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic phosphoric acids and derivatives
• Subclass: Phosphate esters
• Intermediate Tree Nodes: Alkyl phosphates
• Direct Parent: Dialkyl phosphates
• Alternative Parents: Dicarboxylic acids and derivatives Enoate esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl phosphate - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
• 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

Chemical and Physical Properties

• Refractive Index: n20/D 1.47 (lit.)
• Flash Point(°F): Not applicable
• Flash Point(°C): Not applicable
• Boil Point(°C): 221℃ (lit.)
• Molecular Weight: 322.250 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 322.082 Da
• Monoisotopic Mass: 322.082 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 418.000
• 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

References

1. Liwei Sun, Xu Zhang, Jiteng Zhang, Xinmeng Li, Jie Zhao, Rujian Jiang, Lingjie Song, Shifang Luan.  (2024)  Endogenous stimulation-driven Janus mesh with antibacterial, anti-adhesive and prohealing performances for hernia repair.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.152764]

2. Zeqi Zhang, Xiaoying Xu, Xue Bi, Wenchao Zhang, Rongjie Yang.  (2026)  Improvement of flame resistance and mechanical properties of vinyl ester based carbon fiber composites by a reactive phosphonium ionic liquid.  COMPOSITES PART A-APPLIED SCIENCE AND MANUFACTURING,      [PMID:] [10.1016/j.compositesa.2026.109690]