67881-98-5

Basic information

• Product Name: 2-methacryloyloxyethyl phosphorylcholine
• Synonyms: Creatinol O-phosphate Magnesium;2-methacryloyloxyethyl phosphorylcholine;2-(Methacryloyloxy)ethyl 2-(Trimethylammonio)ethyl Phosphate;Phosphoric Acid 2-(Methacryloyloxy)ethyl 2-(Trimethylammonio)ethyl Ester;[2-[[2-(Methacryloyloxy)ethoxy]phosphonyloxy]ethyl]trimethylaminium;Methacrylic acid 2-[[[2-(trimethylaminio)ethoxy]phosphonyl]oxy]ethyl ester;O-[[2-(Methacryloyloxy)ethoxy]phosphonyl]choline;O-[[2-[(2-Methylpropenoyl)oxy]ethoxy]phosphonyl]choline
• CAS NO: 67881-98-5
• Molecular Formula: C₁₁H₂₂NO₆P
• Molecular Weight: 295.27
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds
• Mol File: 67881-98-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 143-148°C
• Appearance: /
• Density: 1.22-1.41 at 21.5-22.4℃
• Vapor Pressure: 0-0Pa at 25℃
• Storage Temp.: 2-8°C
• Water Solubility: 83-86vol% at 20℃ and pH5.9-6.8[vol%]
• CAS DataBase Reference: 2-methacryloyloxyethyl phosphorylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methacryloyloxyethyl phosphorylcholine(67881-98-5)
• EPA Substance Registry System: 2-methacryloyloxyethyl phosphorylcholine(67881-98-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• Hazardous Substances Data: 67881-98-5(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

MPC block copolymers with styrene are biocompatible in nature.

General Description

Methacryloyloxyethyl phosphorylcholine (MPC), containing a phosphorylcholine group in the side chain is a most suitable monomer to mimic the phospholipid polar groups contained with cell membranes. MPC block copolymers are biocompatible in nature; it shows desirable interaction with living tissues. It is hydroscopic in nature.

InChI:InChI=1/C11H22NO6P/c1-10(2)11(13)16-8-9-18-19(14,15)17-7-6-12(3,4)5/h1,6-9H2,2-5H3

Synthetic route

C11H23Br2NO6P(1+)*Cl(1-) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
With zinc In ethanol at 0℃;	86%

Ethylene 2-(methacryloyloxy)ethyl phosphate (82793-19-9) + trimethylamine (75-50-3) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile at 50℃; for 48h; Ring cleavage; Amination;	37%
In acetonitrile at -20 - 60℃; for 36h;
In acetonitrile at -20 - 60℃; for 16h; Sealed tube;	3.1 g

2-Bromoethyl 2-cyanoethyl-2-(methacryloyloxy)ethyl phosphate (190070-82-7) + trimethylamine (75-50-3) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile at 75℃; for 24h; Amination;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: N,N-diisopropylamine tetrazolide / dichloromethane / 0.33 h 2: 4,5-dichloroimidazole / acetonitrile / 16 h / 20 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 4: acetonitrile / 24 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 4 h / -30 - -20 °C 2: acetonitrile / 16 h / -20 - 60 °C / Sealed tube View Scheme

Ethylenedioxy-2-(methacryloyloxy)ethoxyphosphine (24619-52-1) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylamine-N-oxide / acetonitrile / 0.67 h 2: acetonitrile / 48 h / 50 °C View Scheme

2-Bromoethoxy-2-(cyanoethoxy)-2-(methacryloyloxy)ethoxyphosphine (190070-81-6) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 2: acetonitrile / 24 h / 75 °C View Scheme

2-((2-cyanoethoxy)(diisopropylamino)phosphinoxy)ethyl methacrylate (190070-80-5) → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 4,5-dichloroimidazole / acetonitrile / 16 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C 3: acetonitrile / 24 h / 75 °C View Scheme

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + choline phosphoryl chloride → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
In acetonitrile

2,3-dibromo-2-methylpropionic acid hydroxyethyl ester → 2-methacryloyloxyethyl phosphorylcholine (67881-98-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate; triethylamine / acetonitrile / 2.5 h / -5 - 20 °C 2.1: triethylamine / 2 h / 0 - 20 °C 2.2: 1 h / 0 - 20 °C 3.1: zinc / ethanol / 0 °C View Scheme

Upstream product

• 82793-19-9 Ethylene 2-(methacryloyloxy)ethyl phosphate 
• 75-50-3 trimethylamine 
• 190070-82-7 2-Bromoethyl 2-cyanoethyl-2-(methacryloyloxy)ethyl phosphate 
• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 24619-52-1 Ethylenedioxy-2-(methacryloyloxy)ethoxyphosphine 
• 190070-81-6 2-Bromoethoxy-2-(cyanoethoxy)-2-(methacryloyloxy)ethoxyphosphine 
• 190070-80-5 2-Cyanoethoxy(diisopropylamino)-2-(methacryloyloxy)ethoxyphosphine 

Relevant articles and documents

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Synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine

The invention provides a synthetic method of artificial cytomembrane main ingredient 2-methacryloyloxy ethyl phosphorylcholine. The synthetic method comprises the following steps: (1) dissolving phosphorus oxychloride in acetonitrile, adding triethylamine at 0 to 10 DEG C, dropwise adding 2,3-dibromo-2-hydroxyethyl methacrylate, reacting at -10 to 0 DEG C, adding triethylamine and choline chloride to facilitate the reaction at -10 to 0 DEG C, and obtaining bromophosphorylcholine after the reaction is ended; and (2) dissolving the bromophosphorylcholine obtained in the step (1) in ethanol, adding zinc powder, severely stirring, and obtaining 2-methacryloyloxyethyl phosphorylcholine. By adopting the synthetic method, a synthetic route of the original 2-methacryloyloxyethyl phosphorylcholine is simplified, no treatment is needed after the purification during the synthetic route, and the next operation can be directly carried out; severe conditions in the synthetic route are avoided, high-end equipment is not needed, uncontrollable factors during the synthetic route are reduced; raw materials are easy to obtain, the price is low, the cost is reduced, the use of solvents and raw materials with large toxicity is avoided, and the green synthesis is realized; and a foundation is set for the industrialization of the 2-methacryloyloxyethyl phosphorylcholine.