109-16-0

Basic information

• Product Name: Triethylene glycol dimethacrylate
• Synonyms: 1,2-bis(2-(methacryloyloxy)ethoxy)ethane;1,2-Bis[2-(Methacryloyloxy)ethoxy]ethane;2-(2-[2-(Methacryloyloxy)ethoxy]ethoxy)ethyl 2-methylacrylate;2-Propenoicacid,2-methyl-,1,2-ethanediylbis(oxy-2,1-ethanediyl)ester;Ethylenebis(oxyethylene) methacrylate;ethylenebis(oxyethylene)methacrylate;Methacrylic acid, diester with triethylene glycol;methacrylicacid,diesterwithtriethyleneglycol
• CAS NO: 109-16-0
• Molecular Formula: C₁₄H₂₂O₆
• Molecular Weight: 286.32
• EINECS: 203-652-6
• Product Categories: Functional Monomer;Biocompatible/Biodegradable Materials;C12 to C63Materials Science;Carbonyl Compounds;Crosslinking AgentsPolymer Science;Esters;Homobifunctional PEGs;Poly(ethylene glycol) and Poly(ethylene oxide);Aliphatics;Mutagenesis Research Chemicals;Polymer Additives;Crosslinkers;Materials Science;New Products for Materials Research and Engineering;Polymer Science;Dyestuff Intermediates
• Mol File: 109-16-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: -52°C
• Boiling Point: 170-172 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.092 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000119mmHg at 25°C
• Refractive Index: n20/D 1.461(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• Water Solubility: 3.6g/L at 20℃
• Stability: Light Sensitive
• BRN: 1797351
• CAS DataBase Reference: Triethylene glycol dimethacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylene glycol dimethacrylate(109-16-0)
• EPA Substance Registry System: Triethylene glycol dimethacrylate(109-16-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-28-36/37
• RIDADR: UN 3334
• WGK Germany: 1
• RTECS: OZ4100000
• F: 8-19
• Hazardous Substances Data: 109-16-0(Hazardous Substances Data)

Usage

Description

Triethylene glycol dimethacrylate (TEGDMA) is a hydrophilic, low viscosity, difunctional methacrylic monomer used as a crosslinking agent in various applications.

Uses

Used in Coatings and Printing Industry:
Triethylene glycol dimethacrylate is used as a key raw material for producing esters of acrylic acid and methacrylic acid, which are essential in the coatings and printing industry.
Used in Food Packaging:
TEGDMA is used as a key raw material for producing esters of acrylic acid and methacrylic acid, which are also used in food packaging.
Used in Adhesives and Dental Restorative Materials:
Triethylene glycol dimethacrylate is used as a methacrylic monomer for use as a cross-linking agent in adhesives and dental restorative materials.
Used in Dental Resin Materials:
TEGDMA is used as a monomer in dental resin materials that can cause specific stress responses in eukaryotic cells. It is commonly used to aesthetically restore the structure and function of teeth impaired by caries, erosion, or fracture.
Used in Synthesis of Poly (methacrylic acid-g-ethylene glycol) Hydrogels:
Triethylene glycol dimethacrylate is used as a cross-linking agent in the synthesis of poly (methacrylic acid-g-ethylene glycol) hydrogels, which show large changes in swelling due to changes in pH, temperature, and solvent composition.
Used in Copolymers with Divinylbenzene (DVB) and Glycidyl Methacrylate (GMA) or Hydroxyethyl Methacrylate (HEMA) Comonomers:
TEGDMA is used as a divinylic methacrylic monomer, which is widely used to form copolymers with DVB and GMA or HEMA comonomers.
Used in Dimethacrylate Based Dental Composites:
Triethylene glycol dimethacrylate is used as a diluent co-monomer in dimethacrylate-based dental composites.
Used in Atom Transfer Radical Polymerization (ATRP) of Styrene:
TEGDMA is used as a branching agent in the ATRP of styrene.
Used in Dental Bonding Resins and Sealants:
Triethylene glycol dimethacrylate is used as a crosslinking agent of acrylic resins, which are used in dental bonding resins and sealants. These are mainly used in dentistry by dental technicians and dentists.
Used in Dentin Bonding Agents and Composite Resins:
TEGDMA is a resin monomer widely used in the composition of dentin bonding agents and composite resins to restore teeth structures impaired by caries and/or fractures. However, the release of resin monomers into the oral environment can trigger hazardous biological effects on oral tissues. TEGDMA has been reported to cause cytotoxicity, impaired cellular functions, pulpal inflammatory responses, and changes in the immune system. It may also reduce the mineralization capacity of dental pulp cells by decreasing the expression of mineralization-related gene pathways and causing adverse effects.

Reference

Krifka, S, et al. "A review of adaptive mechanisms in cell responses towards oxidative stress caused by dental resin monomers. " Biomaterials 34.19(2013):4555-4563.

InChI:InChI=1/C14H22O6/c1-11(2)13(15)19-9-7-17-5-6-18-8-10-20-14(16)12(3)4/h1,3,5-10H2,2,4H3

Synthetic route

dimethyltin dichloride (753-73-1) + 4-methoxy-phenol (150-76-5) + methacrylic acid methyl ester (80-62-6) → triethyleneglycol dimethacrylate (109-16-0)

Conditions	Yield
With sodium methylate; hydroquinone In n-heptane; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol	91%

Methacryloyl chloride (920-46-7) + 2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol (201037-95-8) → triethyleneglycol dimethacrylate (109-16-0) + 2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate (495417-68-0)

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	A n/a B 81%

Methacryloyl chloride (920-46-7) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0)

Conditions	Yield
With sodium hydroxide

poly(methacrylic acid) (79-41-4) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0)

Conditions	Yield
With sulfuric acid

methacrylic acid methyl ester (80-62-6) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0)

Conditions	Yield
With sodium methylate; hydroquinone

poly(methacrylic acid) (79-41-4) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0) + 2-(2-(2-hydroxyethoxy)ethoxy)ethyl methacrylate (2351-42-0) + ethylene glycol (107-21-1) + diethylene glycol (111-46-6)

Conditions	Yield
toluene-4-sulfonic acid at 70 - 100℃; Kinetics; bulbs method; at various concentrations of catalyst;

2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / pyridine / CH2Cl2 / 20 °C 2: triethylamine / diethyl ether / 20 °C View Scheme

Methacryloyl chloride (920-46-7) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0) + 2-(2-(2-hydroxyethoxy)ethoxy)ethyl methacrylate (2351-42-0)

Conditions	Yield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With pyridine In dichloromethane at 18 - 28℃; for 0.5h; Inert atmosphere; Stage #2: Methacryloyl chloride In dichloromethane at 18 - 28℃; for 4h; Cooling with ice; Inert atmosphere;

5-norbornen-2-yl acetate + triethyleneglycol dimethacrylate (109-16-0) → poly(triethylene glycol dimethacrylate-co-5-norbornen-2-yl acetate)

Conditions	Yield
(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)(η6-p-cymene)RuCl2 for 0.0333333h; blue light irradiation;	99%

triethyleneglycol dimethacrylate (109-16-0) → polymer, crosslinked, obtained by polymerization triethyleneglycol dimethylacrylate, initiated by N-propyloyloxytrimethylammonium tetraphenylborate; monomer(s): triethyleneglycol dimethylacrylate

Conditions	Yield
With sulfuric acid for 0.00416667h;	98%

1,3-diaminohexane + triethyleneglycol dimethacrylate (109-16-0) → Reaxys ID: 11387382

Conditions	Yield
Stage #1: 1,3-diaminohexane With TW-20; sodium carbonate In water Stage #2: triethyleneglycol dimethacrylate In water Stage #3: With adipic acid chloride In chloroform; cyclohexane; water	97%

triethyleneglycol dimethacrylate (109-16-0) + p-toluenesulfonyl iodide (1950-78-3) → triethylene glycol bis[2-(toluene-4-sulfonylmethyl)acrylate]

Conditions	Yield
Stage #1: triethyleneglycol dimethacrylate; p-toluenesulfonyl iodide In dichloromethane at 20℃; for 24h; Stage #2: With triethylamine In dichloromethane at 20℃; for 2h; Stage #3: With triethylamine In ethyl acetate for 6h; Reflux;	81%

triethyleneglycol dimethacrylate (109-16-0) + tartaric acid (87-69-4) → Reaxys ID: 11400417

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 10 - 80℃; for 6h;	75%

triethyleneglycol dimethacrylate (109-16-0) + methacrylic acid methyl ester (80-62-6) + 1-dodecylthiol (112-55-0) → polymer, Mn 5870, PDI 3.44 by SEC; monomer(s): methyl methacrylate; triethylene glycol dimethacrylate; dodecanethiol

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 5h;	65%

styrene (292638-84-7) + triethyleneglycol dimethacrylate (109-16-0) → poly(styrene-co-triethyleneglycol dimethacrylate), crosslinked, radical suspension polymerized, 2 mol percent triethyleneglycol dimethacrylate; monomers: styrene; triethyleneglycol dimethacrylate

Conditions	Yield
With polyvinylalcohol; dibenzoyl peroxide In water; toluene at 80℃; for 8h; Polymerization;	54%

1-ethenyl-2-pyrrolidinone (88-12-0) + triethyleneglycol dimethacrylate (109-16-0) → poly(N-vinylpyrrolidone-2); monomer(s): N-vinyl-2-pyrrolidone + polymer; monomer(s): N-vinyl-2-pyrrolidone, 95 mol percent; triethylene glycol dimethacrylate

Conditions	Yield
at 21.85℃; γ-Irradiation;	A 35% B n/a

1-ethenyl-2-pyrrolidinone (88-12-0) + triethyleneglycol dimethacrylate (109-16-0) → poly(N-vinylpyrrolidone-2); monomer(s): N-vinyl-2-pyrrolidone + polymer; monomer(s): N-vinyl-2-pyrrolidone, 86 mol percent; triethylene glycol dimethacrylate

Conditions	Yield
at 21.85℃; γ-Irradiation;	A 3% B n/a

ethanol (64-17-5) + triethyleneglycol dimethacrylate (109-16-0) → 2-Ethoxy-2-hydroxymethylperoxy-propionic acid 2-{2-[2-(2-ethoxy-2-hydroxymethylperoxy-propionyloxy)-ethoxy]-ethoxy}-ethyl ester (64981-68-6)

Conditions	Yield
With ozone

triethyleneglycol dimethacrylate (109-16-0) + polymer; monomer(s): butyl methacrylate, 67 mol percent; dodecane-1,2-diyl dimethacrylate, 30.0 mol percent; 2,2,3,3,3-pentafluoropropyl methacrylate; 4-[2-(methacryloyloxy)ethoxycarbonyl]benzyl-N,N-diethyldithiocarbamate, 2.0 mol percent; 1,4-bis(Et2NC(S)SCH2)benzene → polymer; monomer(s): butyl methacrylate; dodecane-1,2-diyl dimethacrylate; 2,2,3,3,3-pentafluoropropyl methacrylate; 4-[2-(methacroyloxy)ethoxycarbonyl]benzyl-N,N-diethyldithiocarbamate; 1,4-bis(Et2NC(S)SCH2)benzene; triethylene glycol dimethacrylate

Conditions	Yield
at 20℃; for 0.166667h; UV-irradiation;

styrene (292638-84-7) + triethyleneglycol dimethacrylate (109-16-0) → polymer; monomer(s): tri(ethylene glycol) dimethacrylate, 1.6 wt percent; styrene

Conditions	Yield
With poly(vinyl alcohol); dibenzoyl peroxide In water at 80℃; for 8h;

styrene (292638-84-7) + triethyleneglycol dimethacrylate (109-16-0) → polymer; monomer(s): tri(ethylene glycol) dimethacrylate, 2.2 wt percent; styrene

Conditions	Yield
With poly(vinyl alcohol); dibenzoyl peroxide In water at 80℃; for 8h;

styrene (292638-84-7) + triethyleneglycol dimethacrylate (109-16-0) → polymer; monomer(s): tri(ethylene glycol) dimethacrylate, 2.7 wt percent; styrene

Conditions	Yield
With poly(vinyl alcohol); dibenzoyl peroxide In water at 80℃; for 8h;

styrene (292638-84-7) + triethyleneglycol dimethacrylate (109-16-0) → polymer; monomer(s): tri(ethylene glycol) dimethacrylate, 5.3 wt percent; styrene

Conditions	Yield
With poly(vinyl alcohol); dibenzoyl peroxide In water at 80℃; for 8h;

triethyleneglycol dimethacrylate (109-16-0) + 2-(4-dimethylaminophenyl)ethyl alcohol (50438-75-0) + dibenzoyl peroxide (94-36-0) → polymer; monomer(s): triethylene glycol dimethacrylate; benzoyl peroxide; 4-(N,N-dimethylamino)phenethyl alcohol

Conditions	Yield
at 37℃; Kinetics;

1-ethenyl-2-pyrrolidinone (88-12-0) + triethyleneglycol dimethacrylate (109-16-0) → poly(N-vinylpyrrolidone-2); monomer(s): N-vinyl-2-pyrrolidone + polymer; monomer(s): N-vinyl-2-pyrrolidone, 72 mol percent; triethylene glycol dimethacrylate

Conditions	Yield
at 21.85℃; γ-Irradiation;

1-ethenyl-2-pyrrolidinone (88-12-0) + triethyleneglycol dimethacrylate (109-16-0) → polymer; monomer(s): N-vinyl-2-pyrrolidone, 57 mol percent; triethylene glycol dimethacrylate

Conditions	Yield
at 21.85℃; γ-Irradiation;

triethyleneglycol dimethacrylate (109-16-0) → poly(triethylene glycol dimethacrylate); monomer(s): triethylene glycol dimethacrylate

Conditions	Yield
at 21.85℃; γ-Irradiation;

triethyleneglycol dimethacrylate (109-16-0) → triethylene glycol di-isobutyrate (133176-35-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃;

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 920-46-7 Methacryloyl chloride 
• 753-73-1 dimethyltin dichloride 
• 150-76-5 4-methoxy-phenol 
• 80-62-6 methacrylic acid methyl ester 
• 201037-95-8 2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol 

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Triethylene glycol dimethacrylate (cas 109-16-0) induces large deletions in the hprt gene of V79 cells08/26/2019

Acrylate esters are applied in industrial and consumer products often associated with polymers and resins. The difunctional methacrylate, triethylene glycol dimethacrylate (TEGDMA), is also frequently included in dental composite materials. Recently, mutagenicity testing of the compound revealed...detailed

Novel self-healing dental resin with microcapsules of polymerizable Triethylene glycol dimethacrylate (cas 109-16-0) and N,N-dihydroxyethyl-p-toluidine08/25/2019

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ObjectiveVarious protective effects of N-acetylcysteine (NAC) against triethylene glycol dimethacrylate (TEGDMA)-induced cell damage have been demonstrated, but so far there is no evidence on NAC direct monomer detoxification mechanism. Here, we hypothesized that NAC might reduce TEGDMA cytotoxi...detailed

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Synthesis of water-soluble polymethacrylates by living anionic polymerization of trialkylsilyl-protected oligo(ethylene glycol) methacrylates

2-[2-[(tert-Butyldimethylsilyl)oxy]ethoxy]ethyl methacrylate (2) and 2-[2-[2-[(tert-butyldimethylsilyl)oxy] ethoxy] ethoxy] ethyl methacrylate (3) were polymerized anionically in THF at -78 °C for 2-24 h. The anionic initiator systems included 1,1-diphenyl-3-methylpentyllithium/lithium chloride and diphenylmethylpotassium/diethylzinc. The polymerization of novel tert-butyldimethylsilyl-protected oligo(ethylene glycol) methacrylates, 2 and 3, proceeded quantitatively in each case. The resulting polymers possessed the predicted molecular weights based on the molar ratios of monomers to initiators, and narrow molecular weight distributions (Mw/Mn 1.1). The stability of the propagating carbanion of poly(2) and poly(3) was ascertained by the quantitative efficiencies of the sequential block copolymerizations using tert-butyl methacrylate (tBMA). Well-defined block copolymers, poly(2)-block-poly(tBMA) and poly(3)block-poly(tBMA), were obtained. The trialkylsilyl protecting groups of poly(2) and poly(3) were quantitatively hydrolyzed using 2 N HC1 in aqueous THF at 0 °C for 2 h to give tailored poly[di(ethylene glycol) methacrylate] and poly[tri(ethylene glycol) methacrylate], respectively. Both polymethacrylates obtained after deprotection were readily soluble in water due to the high polarity of the hydrophilic oligo(ethylene glycol) pendant units with terminal OH functionality.