1680-21-3

Basic information

• Product Name: Triethylene glycol diacrylate
• Synonyms: TRIETHYLENE GLYCOL DIACRYLATE;2-Propenoicacid,1,2-ethanediylbis(oxy-2,1-ethanediyl)ester;acrylicacid,diesterwithtriethyleneglycol;1,2-ethanediylbis(oxy-2,1-ethanediyl) diacrylate;TEGdiacrylate;2-PROPENOICACID,1,2-ETHANEDIYLBIS(OXY-2,1-ETHANEDIYL)E.;2,2'-(ethylenedioxy)diethyl diacrylate triethylene glycol diacrylate;2,2'-[Ethylenebis(oxy)]bisethanol diacrylate
• CAS NO: 1680-21-3
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• EINECS: 216-853-9
• Mol File: 1680-21-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 125℃/2mm
• Boiling Point: 266°C
• Flash Point: >100°C
• Appearance: /
• Density: 1,1 g/cm3
• Vapor Pressure: 9.54E-05mmHg at 25°C
• Refractive Index: n20/D1.464
• Storage Temp.: 2-8°C
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Triethylene glycol diacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylene glycol diacrylate(1680-21-3)
• EPA Substance Registry System: Triethylene glycol diacrylate(1680-21-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43-36/38
• Safety Statements: 26-36/37/39-28
• WGK Germany: 3
• RTECS: AS8150000
• Hazardous Substances Data: 1680-21-3(Hazardous Substances Data)

Usage

Uses

Triethylene glycol diacrylate is a cross-linking acrylate monomer for use in coatings, adhesives, and printing plates of the photoprepolymer type.

General Description

Triethyleneglycol dimethacrylate is used as an intermediate product for polymer synthesis in the chemical industry.

Safety Profile

Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental tumorigenic data. Severe skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C12H18O6/c1-3-11(13)17-9-7-15-5-6-16-8-10-18-12(14)4-2/h3-4H,1-2,5-10H2

Synthetic route

acryloyl chloride (814-68-6) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	99%
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With triethylamine In dichloromethane at 0℃; Inert atmosphere; Stage #2: acryloyl chloride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	57%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C46H90O18N2P2 (871982-25-1)

Conditions	Yield
In tert-butyl alcohol at 100℃; for 1h;	70%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, photopolymerization; monomer(s): triethylene glycol diacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone under 3750.3 Torr; for 0.0216667h; Kinetics; Product distribution; UV-irradiation;	63.6%

Cycloheptene (628-92-2) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → (12E,19E)-1,4,7,10-Tetraoxa-cyclohenicosa-12,19-diene-11,21-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	63%

(Z)-Cyclooctene (931-88-4, 931-87-3) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → (12E,20E)-1,4,7,10-Tetraoxa-cyclodocosa-12,20-diene-11,22-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	59%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + cyclododecene (1501-82-2) → (12E,24E)-1,4,7,10-Tetraoxa-cyclohexacosa-12,24-diene-11,26-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	55%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + cyclopentene (142-29-0) → (12E,17E)-1,4,7,10-Tetraoxa-cyclononadeca-12,17-diene-11,19-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	52%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + 3-methyl-1-cyclopentene (1120-62-3) → (12E,17E)-14-Methyl-1,4,7,10-tetraoxa-cyclononadeca-12,17-diene-11,19-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	50%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + cyclohexene (110-83-8) → (12E,18E)-1,4,7,10-Tetraoxa-cycloicosa-12,18-diene-11,20-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	39%

4-methylcyclohexene (591-47-9) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → (12E,18E)-15-Methyl-1,4,7,10-tetraoxa-cycloicosa-12,18-diene-11,20-dione

Conditions	Yield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating;	37%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N,N-dihydroxybenzene-1,3-dicarboximidoyl dichloride (18728-47-7) → C20H22N2O8

Conditions	Yield
With triethylamine In ethanol at 20℃; for 10h;	30%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N,N-dihydroxybenzene-1,4-dicarboximidoyl dichloride (13533-12-5) → C40H44N4O16

Conditions	Yield
With triethylamine In ethanol at 20℃; for 10h;	27%
With triethylamine In ethanol for 14h; Ambient temperature; Yield given;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N,N-dihydroxypyridine-1,3-dicarboximidoyl dichloride (65823-19-0) → C19H21N3O8

Conditions	Yield
With triethylamine In ethanol at 20℃; for 10h;	17%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N,N-dihydroxybenzene-1,3-dicarboximidoyl dichloride (18728-47-7) → C20H22N2O8

Conditions	Yield
With triethylamine In ethanol for 14h; Ambient temperature; Yield given;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N,N-dihydroxypyridine-1,3-dicarboximidoyl dichloride (65823-19-0) → C19H21N3O8

Conditions	Yield
With triethylamine In ethanol for 14h; Ambient temperature; Yield given;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer; monomer(s): acrylic acid 2-[2-(2-acryloyloxyethoxy)ethoxy]ethyl ester

Conditions	Yield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide Electrochemical reaction;

piperazine (110-85-0) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 14800, PDI = 1.98; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; piperazine

Conditions	Yield
In dichloromethane at 45℃; for 120h;

1-(2-aminoethyl)piperidine (27578-60-5) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 3230, PDI = 1.82; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; (2-aminoethyl)piperidine

Conditions	Yield
In dichloromethane at 45℃; for 120h;

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 6830, PDI = 1.93; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 4-(2-aminoethyl)morpholine

Conditions	Yield
In dichloromethane at 45℃; for 120h;

3-(1H-imidazol-1-yl)propan-1-amine (5036-48-6) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 1752, PDI = 1.46; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 1-(3-aminopropyl)imidazole

Conditions	Yield
In dichloromethane at 45℃; for 120h;

hexan-1-amine (111-26-2) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 5640, PDI = 1.85; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; hexylamine

Conditions	Yield
In dichloromethane at 45℃; for 120h;

4-Aminobutanol (13325-10-5) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, Mw = 15300, PDI = 3.92; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 4-amino-butan-1-ol

Conditions	Yield
In dichloromethane at 45℃; for 120h;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + 1,3-di(piperidin-4-yl)propane (16898-52-5) → polymer, Mw = 18700, PDI = 2.72; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 1,3-bispiperidine-4-yl-propan

Conditions	Yield
In dichloromethane at 45℃; for 120h;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + ethanolamine (141-43-5) → polymer, Mw = 7940, PDI = 3.25; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 2-amino-ethanol

Conditions	Yield
In dichloromethane at 45℃; for 120h;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N-butylamine (109-73-9) → polymer, Mw = 5220, PDI = 1.95; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; butylamine

Conditions	Yield
In dichloromethane at 45℃; for 120h;

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + 2-(2-Aminoethoxy)ethanol (929-06-6) → polymer, Mw = 15500, PDI = 4.89; monomer(s): acrylic acid 2-[2-(2-acryloyloxy-ethoxy)-ethoxy]-ethyl ester; 2-(2-aminoethoxy)ethanol

Conditions	Yield
In dichloromethane at 45℃; for 120h;

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, low hydrophobic, prepared by photocopolymerization of monomer and cross-linker; monomer(s): 2-acrylamido-2-methyl-1-propanesulfonic acid; poly(ethylene glycol) diacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; diethyl ether; water for 0.05h; UV-irradiation;

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, low hydrophobic, prepared by photocopolymerization of monomer (25 wt %) and cross-linker (75 wt %); monomer(s): 2-acrylamido-2-methyl-1-propanesulfonic acid; poly(ethylene glycol) diacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; diethyl ether; water for 0.05h; UV-irradiation;

2-Methacryloyloxyethyl-1-sulfonic acid (10595-80-9) + 2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) → polymer, low hydrophobic, prepared by photocopolymerization of monomer, cross-linker and porogen; monomer(s): sulfoethyl methacrylate; poly(ethylene glycol) diacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In diethyl ether for 0.5h; UV-irradiation;

Upstream product

• 814-68-6 acryloyl chloride 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 

Relevant articles and documents

Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: Monomer reactivity and mechanical behavior

Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were obtained.

Multiple Cycloadditive macrocyclization: An Efficient Method for Crown Ether-Type Cyclophanes, Bis-Calix[4]arenes and Silamacrocycles

Macrocycles constitute a broad spectrum of compounds, which play a significant role in host-guest supramolecular chemistry. We have rationally designed an efficient novel synthetic method to synthesize different types of artificial receptive macrocycles containing isoxazoline or isoxazole ring systems. This method involves multiple (double, triple or quadrupole) cycloadditions between bifunctional dipoles and bifunctional dipolarophiles. We have presented our synthetic results to show the ease with which this one-pot synthetic method can be extended to synthesize different types of macrocycles such as cyclophanes, bis-calix[4]arenes and silamacrocycles. Hence, with appropriate combination of bifunctional dipoles and bifunctional dipolarophiles, the ring size of macrocycles could be controlled. This multiple cycloadditive macrocyclization will be a useful arsenal for the synthesis of various macrocycles.