Tetraethylene glycol dimethacrylate CAS#: 109-17-1; ChemWhat Code: 101937

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameTetraethylene glycol dimethacrylate
IUPAC Name2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate
Molecular StructureTetraethylene-glycol-dimethacrylate-CAS-109-17-1
CAS Registry Number 109-17-1
EINECS Number203-653-1
MDL NumberMFCD00014932
Beilstein Registry Number1803537
SynonymsTetraethylene glycol dimethacrylate
109-17-1
TETRAETHYLENEGLYCOL DIMETHACRYLATE
Te EGDMA
Tetraethylene glycol, dimethacrylate
TGM 4
SR 209
Methacrylic acid, oxybis(ethyleneoxyethylene) ester
CT038EQF54
DTXSID6044515
Methacrylic acid, diester with tetraethylene glycol
2-Propenoic acid, 2-methyl-, oxybis(2,1-ethanediyloxy-2,1-ethanediyl) ester
NSC-84253
DTXCID4024515
teegdma
203-653-1
((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate)
PEG-4 dimethacrylate
CCRIS 3435
3,6,9-Trioxaundecamethylene dimethacrylate
EINECS 203-653-1
NSC 84253
BRN 1803537
2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate
TGM-4
MFCD00081877
2-Propenoic acid, 2-methyl-, 1,1′-(oxybis(2,1-ethanediyloxy-2,1-ethanediyl)) ester
Tetraethylene glycol dimethacrylate(7 cp(25 degrees c))
UNII-CT038EQF54
2-Propenoic acid, 2-methyl-, 1,1′-[oxybis(2,1-ethanediyloxy-2,1-ethanediyl)] ester
transglutaminase 5
PEG bismethacrylate
MFCD00014932
SCHEMBL15895
CHEMBL3184138
95% (stabilized with MEHQ)
AAA10917
NSC84253
PEG-4 DIMETHACRYLATE [INCI]
Tox21_300956
NCGC00248228-01
NCGC00254858-01
3,6,9Trioxaundecamethylene dimethacrylate
BS-44110
CAS-109-17-1
Tetraethylene glycol dimethacrylate; TEGDMA
NS00019480
T3486
D84708
F20349
Q27275744
Tetraethylene Glycol Dimethacrylate (stabilized with HQ)
Tetraethylene glycol dimethacrylate, technical, >=90% (GC)
2Propenoic acid, 2methyl, oxybis(2,1ethanediyloxy2,1ethanediyl) ester
((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl)bis(2-methylacrylate)
14-Methyl-13-oxo-3,6,9,12-tetraoxapentadec-14-en-1-yl 2-methylacrylate #
2Propenoic acid, 2methyl, 1,1′(oxybis(2,1ethanediyloxy2,1ethanediyl)) ester
Tetraethylene glycol dimethacrylate, contains <=1500 ppm MEHQ as inhibitor, 95%
Tetraethylene glycol dimethacrylate, contains ~0.006% Hydroquinone as stabilizer, 90%
Molecular FormulaC16H26O7
Molecular Weight330.37
InChIInChI=1S/C16H26O7/c1-13(2)15(17)22-11-9-20-7-5-19-6-8-21-10-12-23-16(18)14(3)4/h1,3,5-12H2,2,4H3
InChI KeyLTHJXDSHSVNJKG-UHFFFAOYSA-N 
SMILESC1CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(=C)C
Patent Information
Patent IDTitlePublication Date
KR2016/49795DENTAL COMPOSITE COMPRISING THE STICKINESS PREVENTING MATERIALS2016
US2003/191338Methods for inhibiting the polymerization of methacrylate monomers2003

Physical Data

AppearanceClear Liquid
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C
1.0818420
1.08720-20

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1H[(2)H6]acetone500

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Tetraethylene glycol dimethacrylate CAS 109-17-1
Route of Synthesis (ROS) of Tetraethylene glycol dimethacrylate CAS 109-17-1
ConditionsYield
Stage #1: tetraethylene glycol dimethacrylate; p-toluenesulfonyl iodide With triethylamine In dichloromethane at 20℃; Irradiation;
Stage #2: With triethylamine In ethyl acetate Inert atmosphere; Reflux;

Experimental Procedure
2 Synthesis of Tetraethylene Glycol bis[2-(toluene-4-sulfonyl-methyl) Acrylate] (2)
Tetraethylene glycol dimethacrylate (TTEGDMA: 5.29 g, 16 mmol) and 4-toluenesulfonyl iodide (9.03 g, 32 mmol) were stirred together in CH2Cl2 (approx. 50 ml) at room temperature in yellow light. The reaction was monitored using 1H-NMR spectroscopy. After all of the TTEGDMA had been used up (decrease in the double-bond signals), the reaction solution was washed with 5 wt.-% sodium dithionite solution (2×25 ml) and with water (1×25 ml). The aqueous phase was re-extracted with CH2Cl2 (1×25 ml) and the combined organic phases were dried over Na2SO4. 50 ml ethyl acetate was then added to the solution and the CH2Cl2 was evaporated on a rotary evaporator. A further 50 ml ethyl acetate was then added to the reaction solution and triethylamine (8.1 g, 80 mmol) was added dropwise under an Ar atmosphere (solid precipitated out). The reaction solution was then boiled under reflux overnight. Once the reaction was complete, the solution was washed with 1N HCl (2×50 ml) and dist. water (1×50 ml). The aqueous phases were re-extracted and the combined organic phases were dried over Na2SO4. The solvent was drawn off on a rotary evaporator and the crude product was purified using column chromatography with a mixture of PE/EE 1/4. (Rf0.32). Yield 70%. 1H-NMR (200 MHz, CDCl3,δ): 7.73 (d, J=8.2 Hz, 4H; Ar-H), 7.32 (d, J=8.2 Hz, 4H; Ar-H), 6.52 (s, 2H; ═CH2), 5.89 (s, 2H; ═CH2), 4.14 (m, 8H; OOC-CH2-, SO2-CH2-), 3.62 (m, 12H; -CH2-O-CH2-CH2-), 2.43 (s, 6H; Ar-CH3). 13C-NMR (50 MHz, CDCl3, δ): 164.9 (C═O), 144.9 (C4), 135.4 (C4), 133.6 (C2), 129.7 (C3), 128.9 (C4), 128.8 (C4), 70.7 (C2), 68.8 (C2), 64.5 (C2), 57.5 (C2), 21.6 (Cl).		70%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH315 (80%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (34.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (65.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (42.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement CodesP261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Other Data

TransportationUnder room temperature for long time; Sealed and keep away from light.
HS Code
StorageUnder room temperature for long time; Sealed and keep away from light.
Shelf Life
Druglikeness
Lipinski rules component
Molecular Weight330.378
logP0.648
HBA7
HBD0
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)80.29
Rotatable Bond (RotB)16
Matching Veber Rules1
Use Pattern
Tetraethylene glycol dimethacrylate#: CAS 109-17-1 is mainly used as a crosslinking agent in photo-curable resins and is widely applied in dental materials, UV-curable coatings, adhesives, and electronic encapsulation to enhance mechanical strength and chemical resistance.

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