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Bisphenol A-glycidyl methacrylate
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  • Name Bisphenol A-glycidyl methacrylate
  • EINECS216-367-7
  • CAS No. 1565-94-2
  • Density1.161 g/mL at 25 °C(lit.)
  • PSA111.52000
  • LogP3.73050
  • SolubilityN/A
  • Melting PointN/A
  • FormulaC29H36 O8
  • Boiling Point670.3±55.0 °C(Predicted)
  • Molecular Weight512.6
  • Flash Point>230 °F
  • Transport InformationN/A
  • AppearanceN/A
  • SafetyMutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes41-43
  • Molecular Structure
    Molecular Structure of 1565-94-2 (2,2-BIS[4-(2-HYDROXY-3-METHACRYLOXYPROPOXY)PHENYL]PROPANE)
  • Hazard SymbolsXi
  • SynonymsXi
  • Article Data4

Bisphenol A-glycidyl methacrylate Synthetic route

79-41-4

poly(methacrylic acid)

1675-54-3

diphenylolpropane diglycidyl ether

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Conditions
ConditionsYield
Stage #1: poly(methacrylic acid); diphenylolpropane diglycidyl ether With 2,6-di-tert-butyl-4-methyl-phenol at 105 - 108℃; for 2.25h;
Stage #2: With N,N'-dimethylbenzylamine at 105℃; for 21h;
Stage #3: With triethyleneglycol dimethacrylate
80-05-7

BPA

106-91-2

2,3-Epoxypropyl methacrylate

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Conditions
ConditionsYield
With N,N'-dimethylbenzylamine at 70℃; for 6h; Inert atmosphere; Green chemistry;
80-62-6

methacrylic acid methyl ester

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium cyanide; 2,4-dimethyl-6-tert-butylphenol / 2 h / 70 - 80 °C / Green chemistry
2: N,N'-dimethylbenzylamine / 6 h / 70 °C / Inert atmosphere; Green chemistry
View Scheme
80-05-7

BPA

80-62-6

methacrylic acid methyl ester

56-81-5

glycerol

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Conditions
ConditionsYield
Stage #1: BPA; glycerol With potassium carbonate; Diethyl carbonate at 110℃; for 18h;
Stage #2: methacrylic acid methyl ester In dimethyl sulfoxide at 110℃;
5581-32-8

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol

80-62-6

methacrylic acid methyl ester

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Conditions
ConditionsYield
With potassium carbonate at 90℃; for 18h; Temperature;
30674-80-7

2-Isocyanatoethyl methacrylate

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

106884-07-5

2,2-bis-4(3-methacryloxy-2-hydroxypropoxy)phenylpropane diurethane dimethacrylate

Conditions
ConditionsYield
In tetrahydrofuran at 40℃; for 24h;95%
1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

poly[2-methacrylic acid 2-hydroxy-3-[4-(1-{4-[2-hydroxy-3-(methacryloyloxy)-propoxy]-phenyl}-1-methyl-ethyl)-phenoxy]-propyl ester], photocured stereolithography

poly[2-methacrylic acid 2-hydroxy-3-[4-(1-{4-[2-hydroxy-3-(methacryloyloxy)-propoxy]-phenyl}-1-methyl-ethyl)-phenoxy]-propyl ester], photocured stereolithography

Conditions
ConditionsYield
With Camphorquinone UV-irradiation;
109-16-0

triethyleneglycol dimethacrylate

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Reaxys ID: 15741488

Reaxys ID: 15741488

Conditions
ConditionsYield
With water; sodium dodecyl-sulfate; Camphorquinone Product distribution / selectivity; Irradiation with visible light;
With water; sodium dodecyl-sulfate; N,N-bis-(2-hydroxyethyl)-P-toluidine; dibenzoyl peroxide Product distribution / selectivity; Irradiation with light;
With sodium dodecyl-sulfate; N,N-bis-(2-hydroxyethyl)-P-toluidine; dibenzoyl peroxide Product distribution / selectivity; Irradiation with light;
109-16-0

triethyleneglycol dimethacrylate

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Reaxys ID: 15741440

Reaxys ID: 15741440

Conditions
ConditionsYield
With ethyl p-dimethyaminolbenzoate; (1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione at 40℃; for 13h; Reactivity; Under yellow light;
109-16-0

triethyleneglycol dimethacrylate

1565-94-2

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate

Reaxys ID: 15741444

Reaxys ID: 15741444

Conditions
ConditionsYield
With ethyl p-dimethyaminolbenzoate; (1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione at 40℃; for 13h; Reactivity; Under yellow light;

Bisphenol A-glycidyl methacrylate Chemical Properties

Molecular Formula: C29H36O8
Molar mass: 512.59 g/mol
EINECS: 216-367-7
Density: 1.161 g/cm3
Flash Point: 214.6 °C
Index of Refraction: 1.542
Boiling Point: 670.3 °C at 760 mmHg
Vapour Pressure: 7E-19 mmHg at 25°C
Product categories of Boron trifluoride dihydrate (1565-94-2): Acrylic Monomers;Bisphenol Acrylics
Structure of Boron trifluoride dihydrate (1565-94-2):

XLogP3-AA: 5.1
H-Bond Donor: 2
H-Bond Acceptor: 8
Systematic Name: [2-Hydroxy-3-[4-[1-[4-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propoxy]phenyl]-1-methyl-ethyl]phenoxy]propyl] 2-methylprop-2-enoate 
SMILES: O=C(OCC(O)COc1ccc(cc1)C(c2ccc(OCC(O)COC(=O)\C(=C)C)cc2)(C)C)\C(=C)C 
InChI: InChI=1/C29H36O8/c1-19(2)27(32)36-17-23(30)15-34-25-11-7-21(8-12-25)29(5,6)22-9-13-26(14-10-22)35-16-24(31)18-37-28(33)20(3)4/h7-14,23-24,30-31H,1,3,15-18H2,2,4-6H3 
InChIKey: AMFGWXWBFGVCKG-UHFFFAOYAI 
Std. InChI: InChI=1S/C29H36O8/c1-19(2)27(32)36-17-23(30)15-34-25-11-7-21(8-12-25)29(5,6)22-9-13-26(14-10-22)35-16-24(31)18-37-28(33)20(3)4/h7-14,23-24,30-31H,1,3,15-18H2,2,4-6H3 
Std. InChIKey: AMFGWXWBFGVCKG-UHFFFAOYSA-N

Bisphenol A-glycidyl methacrylate Toxicity Data With Reference

1.    

mic-sat 800 µLg/plate

     TOLED5    Toxicology Letters. (Elsevier Scientific Publishing Co., P.O. Box 211, Amsterdam, Netherlands) V.1- 1977- 31 (Suppl),(1986),214.
2.    

dni-hmn-hla 80 µmol/L

     MUREAV    Mutation Research. 368 (1996),181.

Bisphenol A-glycidyl methacrylate Consensus Reports

Reported in EPA TSCA Inventory.

Bisphenol A-glycidyl methacrylate Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
 

Hazard Codes: Xi
Risk Statements:
41:  Risk of serious damage to eyes
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

Bisphenol A-glycidyl methacrylate Specification

 Boron trifluoride dihydrate (1565-94-2) also can be called Silux ; Adaptic ; Panavia opaque ; Bis-gma ; 2,2-Propanediylbis(4,1-phenyleneoxy-2-hydroxy-3,1-propanediyl) bis(2-methylacrylate) ;and 2-propenoic acid, 2-methyl-, (1-methylethylidene)bis(4,1-phenyleneoxy-2-hydroxy-3,1-propanediyl) ester .

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