1565-94-2

Basic information

• Product Name: 2,2-BIS[4-(2-HYDROXY-3-METHACRYLOXYPROPOXY)PHENYL]PROPANE
• Synonyms: Bisphenol A-Glycidyl Methacrylate (BIS-GMA);Charisma Opal;CN 151;Craynor CN 151;Derakane 411-35;D-GMA;Dion VER 44070-00;Dow 411-35
• CAS NO: 1565-94-2
• Molecular Formula: C₂₉H₃₆O₈
• Molecular Weight: 512.59
• EINECS: 216-367-7
• Product Categories: Acrylic Monomers;Bisphenol Acrylics;Monomers
• Mol File: 1565-94-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 670.3±55.0 °C(Predicted)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.161 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.552(lit.)
• Storage Temp.: 2-8°C
• PKA: 12?+-.0.20(Predicted)
• CAS DataBase Reference: 2,2-BIS[4-(2-HYDROXY-3-METHACRYLOXYPROPOXY)PHENYL]PROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-BIS[4-(2-HYDROXY-3-METHACRYLOXYPROPOXY)PHENYL]PROPANE(1565-94-2)
• EPA Substance Registry System: 2,2-BIS[4-(2-HYDROXY-3-METHACRYLOXYPROPOXY)PHENYL]PROPANE(1565-94-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41-43
• Safety Statements: 26-36-36/37/39
• WGK Germany: 1
• RTECS: UD3438000
• Hazardous Substances Data: 1565-94-2(Hazardous Substances Data)

Usage

Description

Bisphenol A glycidyl methacrylate (bis-GMA) is an epoxy-methacrylate. Sensitization occurs in dentists.

Uses

The Progress in Development of Dental Restorative Materials

InChI:InChI=1/C22H24O4/c1-15(4-11-20-14-25-20)21(24)26-19-12-7-17(8-13-19)22(2,3)16-5-9-18(23)10-6-16/h4-10,12-13,20,23H,11,14H2,1-3H3/b15-4+

Synthetic route

poly(methacrylic acid) (79-41-4) + diphenylolpropane diglycidyl ether (1675-54-3) → (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2)

Conditions	Yield
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

BPA (80-05-7) + 2,3-Epoxypropyl methacrylate (106-91-2) → (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2)

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

methacrylic acid methyl ester (80-62-6) → (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2)

Conditions	Yield
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

BPA (80-05-7) + methacrylic acid methyl ester (80-62-6) + glycerol (56-81-5) → (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2)

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

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol (5581-32-8) + methacrylic acid methyl ester (80-62-6) → (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2)

Conditions	Yield
With potassium carbonate at 90℃; for 18h; Temperature;

2-Isocyanatoethyl methacrylate (30674-80-7) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → 2,2-bis-4(3-methacryloxy-2-hydroxypropoxy)phenylpropane diurethane dimethacrylate (106884-07-5)

Conditions	Yield
In tetrahydrofuran at 40℃; for 24h;	95%

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → 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	Yield
With Camphorquinone UV-irradiation;

triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → Reaxys ID: 15741488

Conditions	Yield
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;

triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → Reaxys ID: 15741440

Conditions	Yield
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;

triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → Reaxys ID: 15741444

Conditions	Yield
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;

triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → Reaxys ID: 15741443

Conditions	Yield
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;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → Reaxys ID: 15741593

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dibenzoyl peroxide at 37℃; for 24.25h; Product distribution / selectivity;
With N,N-bis-(2-hydroxyethyl)-P-toluidine at 37℃; for 24.25h; Product distribution / selectivity;

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) + 2-methacryloyloxyethyl hydrogen succinate (20882-04-6) → TrisMAS

Conditions	Yield
Stage #1: (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate; 2-methacryloyloxyethyl hydrogen succinate With dmap In ethyl acetate at 0℃; for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In ethyl acetate for 1h;

Mono(2-methacryloyloxy)ethylphthalate + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → TrisMAP (1150314-29-6)

Conditions	Yield
Stage #1: Mono(2-methacryloyloxy)ethylphthalate; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With dmap In ethyl acetate at 0℃; for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In ethyl acetate for 1h;

2,2'-bi(4-acryloylthiomethyl-1,3-dithiolan) (475577-75-4) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → poly(2,2'-bi(4-acryloylthiomethyl-1,3-dithiolan)-co-epoxy methacrylate of bisphenol A diglycidyl ether)

Conditions	Yield
Stage #1: 2,2'-bi(4-acryloylthiomethyl-1,3-dithiolan); (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With 2-hydroxy-2-methylpropiophenone for 0.0333333h; ultraviolet ray emitted from a metal halide lamp (12; Stage #2: at 100℃; for 1h;

2-acryloylthiomethyl-4-acryloyloxymethyl-1,3-dithiolan (475577-89-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → poly(2-acryloylthiomethyl-4-acryloyloxymethyl-1,3-dithiolan-co-epoxy methacrylate of bisphenol A diglycidyl ether)

Conditions	Yield
Stage #1: 2-acryloylthiomethyl-4-acryloyloxymethyl-1,3-dithiolan; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With 2-hydroxy-2-methylpropiophenone for 0.0166667h; ultraviolet ray emitted from a metal halide lamp; Stage #2: at 80℃; for 1h;

2,4-bis(acryloylthiomethyl)-1,3-dithiolan (475577-93-6) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → poly(2,4-bis(acryloylthiomethyl)-1,3-dithiolan-co-epoxy methacrylate of bisphenol A diglycidyl ether)

Conditions	Yield
Stage #1: 2,4-bis(acryloylthiomethyl)-1,3-dithiolan; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With 2-hydroxy-2-methylpropiophenone for 0.0166667h; ultraviolet ray emitted from a metal halide lamp; Stage #2: at 80℃; for 1h;

bis[4-(acryloylthiomethyl)-1,3-dithiolan-2-ylmethylthio]methane (475578-01-9) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → poly(bis[4-(acryloylthiomethyl)-1,3-dithiolan-2-ylmethylthio]methane-co-epoxy methacrylate of bisphenol A diglycidyl ether)

Conditions	Yield
Stage #1: bis[4-(acryloylthiomethyl)-1,3-dithiolan-2-ylmethylthio]methane; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With 2-hydroxy-2-methylpropiophenone for 0.0166667h; ultraviolet ray emitted from a metal halide lamp; Stage #2: at 80℃; for 1h;

polymethylmethacrylate + triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → prepreg

Conditions	Yield
Stage #1: triethyleneglycol dimethacrylate; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate Stage #2: polymethylmethacrylate In tetrahydrofuran

(1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) + 1,1'-carbonyldiimidazole (530-62-1) → DIZ-BisGMA (872052-66-9)

Conditions	Yield
In dichloromethane at 20℃; for 4h; Inert atmosphere;

triethyleneglycol dimethacrylate (109-16-0) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → poly{2,2-bis[p-(3-methacryloxy-2-hydroxypropoxy)phenyl]propane-co-triethylene glycol dimethacrylate}

Conditions	Yield
for 0 - 0.0833333h; Conversion of starting material; UV-irradiation;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + Pyromellitic dianhydride (89-32-7) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → C100H98O41

Conditions	Yield
Stage #1: Pyromellitic dianhydride; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With dmap In tetrahydrofuran at 45 - 66℃; for 2h; Stage #2: 2-methyl-2-propenoic acid 2-hydroxyethyl ester In tetrahydrofuran for 2h; Reflux;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + Pyromellitic dianhydride (89-32-7) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → C61H60O26

Conditions	Yield
Stage #1: Pyromellitic dianhydride; (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate With dmap In tetrahydrofuran at 45 - 66℃; for 3h; Stage #2: 2-methyl-2-propenoic acid 2-hydroxyethyl ester In tetrahydrofuran for 2h; Reflux;

glutaric anhydride, (108-55-4) + (1-methylethylidene)bis[4,1-phenyleneoxy(2-hydroxy-3,1-propanediyl)] bismethacrylate (1565-94-2) → bisGMA diglutarate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol at 100℃;

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 1675-54-3 diphenylolpropane diglycidyl ether 
• 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 
• 80-05-7 BPA 
• 56-81-5 glycerol 
• 106-91-2 2,3-Epoxypropyl methacrylate 

Downstream Products

• 106884-07-5 2,2-bis-4(3-methacryloxy-2-hydroxypropoxy)phenylpropane diurethane dimethacrylate 
• 872052-66-9 DIZ-BisGMA 
• 1150314-29-6 TrisMAP 

Relevant articles and documents

METHODS OF MAKING VINYL ESTER RESINS AND STARTING MATERIALS FOR THE SAME

Various embodiments of the present invention relate to methods of making bis(hydroxyhydrocarbyl)ethers of bisphenols and vinyl ester resins. In various embodiments, the present invention provides a method for producing a vinyl ester resin (VER). The method can include a bisphenol or a bis(hydroxy((C1-C10)hydrocarbyl)ether of the bisphenol with a vinyl ester to form the VER.

DENTAL MATERIALS AND METHOD OF MANUFACTURE

Dental materials may be made from polyhydric phenols that are non-genotoxic and exhibit estrogenic activity less than that of bisphenol S, while exhibiting properties such as strength and flexibility comparable to those of conventional BPA-derived dental materials.