5039-78-1

Basic information

• Product Name: Methacrylatoethyl trimethyl ammonium chloride
• Synonyms: 2-(METHACRYLOYLOXY)ETHYLTRIMETHYLAMMONIUM CHLORIDE;N,N-DIMETHYLAMINOETHYL METHACRYLATE Q SALT, METHYL CHLORIDE;TMAEMC;TRIMETHYL-2-METHACROYLOXYETHYLAMMONIUM CHLORIDE;TRIMETHYLAMMONIUMETHYLMETHACRYLIC CHLORIDE;Methacrylatoethyl trimethyl Ammonium chloride (70% Aq.);N,N-Dimethylaminoethyl methacrylate Q Salt;(Methacryloyloxyethyl)trimethylammonium Cl.
• CAS NO: 5039-78-1
• Molecular Formula: C₉H₁₈NO₂*Cl
• Molecular Weight: 207.7
• EINECS: 225-733-5
• Product Categories: Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Acrylic Monomers;Methacrylate;Monomers
• Mol File: 5039-78-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: -25°C
• Boiling Point: >100°C
• Flash Point: >100°C
• Appearance: aqueous solution
• Density: 1.105 g/mL at 25 °C
• Refractive Index: n20/D 1.469
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: It is soluble in water.
• Stability: Stable. Incompatible with steel, rust, reducing agents, heavy metal salts, carbon dioxide, oxidizing agents. May be prone to haz
• BRN: 8168395
• CAS DataBase Reference: Methacrylatoethyl trimethyl ammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methacrylatoethyl trimethyl ammonium chloride(5039-78-1)
• EPA Substance Registry System: Methacrylatoethyl trimethyl ammonium chloride(5039-78-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/38-43-36
• Safety Statements: 26-36-36/37-24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 5039-78-1(Hazardous Substances Data)

Usage

Chemical Properties

aqueous solution

Uses

2-(Methacryloyloxy)ethyltrimethylammonium chloride is a zirconium, aluminum and organic surface treated multipurpose rutile titanium dioxide pigment, it has narrow-size material distribution, good whiteness and high weather resistance. It is widely used in coating, plastics, paints, rubber and ink production, leather, cosmetics, soaps, plastics and in paper industry.

InChI:InChI=1/C9H18NO2.ClH/c1-8(2)9(11)12-7-6-10(3,4)5;/h1,6-7H2,2-5H3;1H/q+1;/p-1

Synthetic route

methylene chloride (74-87-3) + 2-(dimethylamino)ethyl methacrylate (2867-47-2) → [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1)

Conditions	Yield
In acetone
In water at 60℃;

potassium 3,6-dichloro-2-methoxybenzoate (10007-85-9) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → [2-(methacryloyloxy)ethyl]trimethylammonium 3,6-dichloro-2-methoxybenzoate

Conditions	Yield
In methanol at 20℃; for 1.5h; Green chemistry;	99%

4-Chloro-2-methylphenoxyacetic acid potassium salt (5221-16-9) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → [2-(methacryloyloxy)ethyl]trimethylammonium (4-chloro-2-methylphenoxy)acetate

Conditions	Yield
In methanol at 20℃; for 1.5h; Green chemistry;	98%

bis(trifluoromethane)sulfonimide lithium (90076-65-6) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → N-[2-(methacryloyloxy)ethyl]-N,N,N-trimethylammonium bis(trifluoromethylsulfonyl)imide (676257-10-6)

Conditions	Yield
In water at 20℃; for 3h; Large scale;	96.3%
In water at 20 - 70℃; Inert atmosphere;
In water at 20℃;
In water
In water at 0℃; for 1h;

2,4-dichlorophenoxyacetic acid potassium (14214-89-2) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → [2-(methacryloyloxy)ethyl]trimethylammonium (2,4-dichlorophenoxy)acetate

Conditions	Yield
In methanol at 20℃; for 1.5h; Green chemistry;	95%

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + mecoprop, potassium salt → [2-(methacryloyloxy)ethyl]trimethylammonium 2-(4-chloro-2-methylphenoxy)propioniate

Conditions	Yield
In methanol at 20℃; for 1.5h; Green chemistry;	94%

poly(ethylene oxide)-2000 methyl ether methacrylate, Mn 2080 g/mol + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → poly{[(2-methacryloyloxyethyl)trimethylammonium chloride]-co-[poly(ethylene glycol)-2000 methyl ether methacrylate]}, Mw 470 kDa, Mw/Mn 2.8, 1 ammonium group containing unit per 45 poly(ethylene glycol) ester containing units

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In water; isopropyl alcohol at 60℃; for 20h;	90.3%

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → 2-(methylacryloyloxy)ethyl-trimethylammonium tetrafluoroborate

Conditions	Yield
With sodium tetrafluoroborate In acetonitrile	90%
With sodium tetrafluoroborate In water for 0.25h;

sodium methacrylate (5536-61-8) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → 2-(methacryloyloxy)-N,N,N-trimethylethan-1-aminium methacrylate

Conditions	Yield
In water; acetone at 50 - 55℃; for 24h;	86.9%

sodium salicylate (54-21-7) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → [2-(methacryloyloxy)ethyl]trimethylammoniumsalicylate

Conditions	Yield
In water at 20℃; for 24h;	62%

sodium dodecyl-sulfate (151-21-3) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → (2-(methacryloyloxy)-N,N,N-trimethylethan-1-aminium dodecyl sulfate)

Conditions	Yield
In ethanol; water at 50 - 55℃; for 24h;	45.5%

methacrylic acid methyl ester (80-62-6) + [2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → poly(trimethylaminoethyl methacrylate chloride -co- methyl methacrylate)

Conditions	Yield
In ethanol at 75℃; for 24h; Polymerization;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + polymer, Mn 10000 Da; monomer(s): 3,6,9,12,15,18,21-heptaoxadocos-1-yl 2-bromo-2-methylpropanoate; 2-methacryloyloxyethyl phosphorylcholine → polymer, Mn 16000 Da; monomer(s): 3,6,9,12,15,18,21-heptaoxadocos-1-yl 2-bromo-2-methylpropanoate; 2-methacryloyloxyethyl phosphorylcholine; 2-(methacryloyloxy)-N,N,N-trimethylethanaminium chloride

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 48h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + glycerol α-monomethacrylate → polymer, diblock copolymer, Mn 13400, Mw/Mn 1.29 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride; glycerol α-monomethacrylate

Conditions	Yield
Stage #1: glycerol α-monomethacrylate With [2,2]bipyridinyl; radical initiator; copper(I) bromide In water; isopropyl alcohol at 20℃; Stage #2: [2-(methacryloyloxy)ethyl]trimethylammonium chloride In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 9700, Mw/Mn 1.20 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 18h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 13400, Mw/Mn 1.25 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 17h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 21400, Mw/Mn 1.23 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 24h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 12100, Mw/Mn 1.21 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 18400, Mw/Mn 1.28 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 1000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 24900, Mw/Mn 1.29 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 10100, Mw/Mn 1.22 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 16h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 12500, Mw/Mn 1.26 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 16h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 19600, Mw/Mn 1.26 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In methanol; water at 20℃; for 16h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 12200, Mw/Mn 1.23 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 18100, Mw/Mn 1.30 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) + poly(ethylene oxide), 2-bromoisobutyroyloxy-terminated, Mn 2000, Mw/Mn 1.1 → poly([2-(methacryloyloxy)ethyl]trimethylammonium chloride-block-poly(ethylene oxide)), Mn 24400, Mw/Mn 1.29 by GPC

Conditions	Yield
With [2,2]bipyridinyl; copper(I) bromide In water; isopropyl alcohol at 20℃;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → polymer, Mn 23000, Mw/Mn 1.37 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride

Conditions	Yield
With [2,2]bipyridinyl; radical initiator; copper(I) bromide In water at 20℃; for 0.5h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → polymer, Mn 13600, Mw/Mn 1.32 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride

Conditions	Yield
With [2,2]bipyridinyl; radical initiator; copper(I) bromide In water at 20℃; for 2.33h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → polymer, Mn 13000, Mw/Mn 1.28 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride

Conditions	Yield
With [2,2]bipyridinyl; radical initiator; copper(I) bromide In water at 20℃; for 1.5h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → polymer, Mn 10100, Mw/Mn 1.18 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride

Conditions	Yield
With [2,2]bipyridinyl; radical initiator; copper(I) bromide In methanol; water at 20℃; for 15h;

[2-(methacryloyloxy)ethyl]trimethylammonium chloride (5039-78-1) → polymer, Mn 12800, Mw/Mn 1.23 by GPC; monomer(s): [2-(methacryloyloxy)ethyl]trimethylammonium chloride

Conditions	Yield
With [2,2]bipyridinyl; radical initiator; copper(I) bromide In methanol; water at 20℃; for 20h;

Upstream product

• 74-87-3 methylene chloride 
• 2867-47-2 2-(dimethylamino)ethyl methacrylate 

Downstream Products

• 27328-61-6 3-(Dodecylthio)-2-methylpropanoic Acid 
• 67-48-1 choline chloride 
• 35429-19-7 poly( N,N,N-trimethyl-2-[(2-methyl-1-oxo-2-propenyl)oxy] ethanaminium chloride-co-2-propeneamide) 
• 82107-56-0 [2-(methacryloyloxy)ethyl]trimethylammonium p-dodecylbenzenesulfonate 

Relevant articles and documents

PROCESS FOR UNSATURATED QUATERNARY AMMONIUM SALT

An unsaturated quaternary ammonium salt is produced by a process that includes reacting methyl chloride in a first vessel with a stoichiometric excess of an unsaturated tertiary amine in the presence of water to form a reaction mixture that includes the unsaturated quaternary ammonium salt and residual unsaturated tertiary amine. The reaction mixture is transferred to a second vessel and phase separated to yield a first fraction in which the unsaturated quaternary ammonium salt is concentrated, and a second fraction in which the residual unsaturated tertiary amine is concentrated. At least a portion of the second fraction is recycled from the second vessel to the first vessel for use in the reaction with methyl chloride. The process, which is preferably operated continuously, allows the use of reduced reaction pressures compared to processes utilizing a stoichiometric excess of methyl chloride, and it also reduces or eliminates the problems associated with recycling methyl chloride and removing methyl chloride from the unsaturated quaternary ammonium salt product.