3739-67-1

Basic information

• Product Name: Bisphenol A bisallyl ether
• Synonyms: 4,4'-isopropylidenebis[(allyloxy)benzene];Bisphenol A diallyl ether;1,1'-(1-Methylethylidene)bis[4-(2-propenyloxy)benzene];BBE;Bisphenol A bisallyl ether;PARA-DIALLYL ETHER BISPHENOL-A;DIALLYLETHER BISPHENOL A;3,3'-[Dimethylmethylenebis(4,1-phenyleneoxy)]bis(1-propene)
• CAS NO: 3739-67-1
• Molecular Formula: C₂₁H₂₄O₂
• Molecular Weight: 308.41
• EINECS: 223-123-3
• Mol File: 3739-67-1.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 430.5 °C at 760 mmHg
• Flash Point: 155.3 °C
• Appearance: off-yellow liquid
• Density: 1.005 g/cm³
• Vapor Pressure: 3.25E-07mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: Bisphenol A bisallyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Bisphenol A bisallyl ether(3739-67-1)
• EPA Substance Registry System: Bisphenol A bisallyl ether(3739-67-1)

Safety Data

• Hazardous Substances Data: 3739-67-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H24O2/c1-5-15-22-19-11-7-17(8-12-19)21(3,4)18-9-13-20(14-10-18)23-16-6-2/h5-14H,1-2,15-16H2,3-4H3

Synthetic route

BPA (80-05-7) + allyl bromide (106-95-6) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;	99%

BPA (80-05-7) + 3-chloroprop-1-ene (107-05-1) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With potassium carbonate; sodium iodide In ethanol for 24h; Heating;	98%
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide at 40℃; for 6h;	70%
With sodium hydroxide; calcium oxide In tert-butyl alcohol at 80℃; for 6h; Solvent; Reagent/catalyst; Temperature;
Stage #1: BPA With sodium hydroxide In ethanol at 78℃; for 8h; Stage #2: 3-chloroprop-1-ene at 70℃; for 6h;

BPA (80-05-7) + allyl methyl carbonate (35466-83-2) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 25℃; for 24h; Condensation;	98%
With potassium carbonate In neat (no solvent) at 85℃; for 4h; Catalytic behavior;	98%

BPA (80-05-7) + Allyl acetate (591-87-7) + triphenylphosphine (603-35-0) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With sodium hydroxide; palladium diacetate In water	95.2%

BPA (80-05-7) + allyl alcohol (107-18-6) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: allyl alcohol With carbonic acid dimethyl ester; sodium methylate at 15.5 - 23℃; for 0.216667h; Inert atmosphere; Stage #2: BPA; 5%-palladium/activated carbon; triphenylphosphine at 22 - 78℃; for 9.68h;	94.17%
With bis(η3-allyl-μ-chloropalladium(II)); silver trifluoromethanesulfonate; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin) In toluene at 40℃; for 38h; Inert atmosphere; Schlenk technique; Molecular sieve; Green chemistry; chemoselective reaction;	77%

BPA (80-05-7) + diallylcarbonate (15022-08-9) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With tetrabutylammomium bromide at 120℃; for 20h; Inert atmosphere;	77%

BPA (80-05-7) + Allyl ether (557-40-4) → 2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol (109348-07-4) + 2,2-bis(3-allyl-4-hydroxyphenyl)propane (1745-89-7) + C21H24O2 (105577-85-3) + 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); silver(I) 4-methylbenzenesulfonate; toluene-4-sulfonic acid In toluene for 0.0833333h; Inert atmosphere; Stage #2: Allyl ether In toluene at 60℃; for 3h; Inert atmosphere;	A n/a B n/a C n/a D n/a E 51%

BPA (80-05-7) + allyl alcohol (107-18-6) → 2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol (109348-07-4) + 2,2-bis(3-allyl-4-hydroxyphenyl)propane (1745-89-7) + C21H24O2 (105577-85-3) + 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With silver(I) 4-methylbenzenesulfonate; toluene-4-sulfonic acid In toluene for 0.0833333h; Inert atmosphere; Stage #2: allyl alcohol In toluene at 80℃; for 3h; Inert atmosphere;	A n/a B n/a C n/a D n/a E 25%

BPA (80-05-7) + Allyl ether (557-40-4) → 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With (2,2-dimethylpropane-1,3-diyl)bis(diphenylphosphane); palladium diacetate In toluene for 0.0833333h; Inert atmosphere; Stage #2: Allyl ether In toluene at 100℃; for 20h; Inert atmosphere;	A n/a B 24%

BPA (80-05-7) + Allyl acetate (591-87-7) → 2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol (109348-07-4) + 2,2-bis(3-allyl-4-hydroxyphenyl)propane (1745-89-7) + C21H24O2 (105577-85-3) + 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With [RuCp(PPh3)2](OTs); silver(I) 4-methylbenzenesulfonate; toluene-4-sulfonic acid In toluene for 0.0833333h; Inert atmosphere; Stage #2: Allyl acetate In toluene at 60℃; for 3h; Inert atmosphere;	A n/a B n/a C n/a D n/a E 18%

BPA (80-05-7) + allyl alcohol (107-18-6) → 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: BPA With (2,2-dimethylpropane-1,3-diyl)bis(diphenylphosphane); palladium diacetate In toluene for 0.0833333h; Inert atmosphere; Stage #2: allyl alcohol In toluene at 100℃; for 3h; Inert atmosphere;	A n/a B 10%

BPA (80-05-7) + Allyl acetate (591-87-7) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
chloro(cyclopentadienyl)[1,2-bis(diphenylphosphinyl)ethane]ruthenium(II) at 95℃; for 4h;
chloro(cyclopentadienyl)[1,2-bis(diphenylphosphinyl)ethane]ruthenium(II) In water at 95℃; for 4h;

BPA (80-05-7) + Allyl acetate (591-87-7) → 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
chloro(cyclopentadienyl)bis(triphenylphosphinyl) ruthenium(II) at 95℃; for 6h;
With crosslinked styrene polymer supported triphenylphosphine; palladium diacetate at 95℃; for 4h;
With triphenylphosphine; palladium diacetate at 95℃; for 4h;

BPA (80-05-7) + 3-chloroprop-1-ene (107-05-1) → 4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With potassium hydroxide In diethylene glycol dimethyl ether; water; dimethyl sulfoxide at 25 - 45℃; for 16h;

BPA (80-05-7) + allyl methyl carbonate (35466-83-2) + diallylcarbonate (15022-08-9) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
With triphenylphosphine; 5%-palladium/activated carbon at 78℃; for 9.68333h;

bis-(4-hydroxyphenyl)methane (620-92-8) + 3-chloroprop-1-ene (107-05-1) → bisphenol A diallyl ether (3739-67-1)

Conditions	Yield
Stage #1: bis-(4-hydroxyphenyl)methane With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Stage #2: 3-chloroprop-1-ene at 85℃; for 7h;	312.8 g

methylthiol (74-93-1) + bisphenol A diallyl ether (3739-67-1) → (((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(propane-3,1-diyl))bis(methylsulfane)

Conditions	Yield
With C38H28Au2F12FeN2O8P2S4 In 1,4-dioxane at 45℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;	99%

bisphenol A diallyl ether (3739-67-1) → 4,4'-isopropylidenediphenol dipropyl ether (122165-67-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In chloroform for 3h;	98%

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol (59501-41-6) + bisphenol A diallyl ether (3739-67-1) → C18H22O4 (13634-08-7) + 3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol (5581-32-8)

Conditions	Yield
With potassium osmate(VI); water; 4-methylmorpholine N-oxide In tert-butyl alcohol at 25℃; for 43h; Product distribution / selectivity;	A 2.8% B 97.2%

bisphenol A diallyl ether (3739-67-1) → 2,2-bis(3-allyl-4-hydroxyphenyl)propane (1745-89-7)

Conditions	Yield
at 160 - 180℃; for 4h;	95%
In various solvent(s) at 199.9 - 204.9℃; for 5h;	65%
With boron trichloride In dichloromethane Claisen rearrangement;

bisphenol A diallyl ether (3739-67-1) → 3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol (5581-32-8)

Conditions	Yield
With potassium osmate(VI); water; 4-methylmorpholine N-oxide In tert-butyl alcohol at 25℃; for 18h; Product distribution / selectivity;	84%

bisphenol A diallyl ether (3739-67-1) → bisphenol A monoglycidyl ether (140896-80-6) + diphenylolpropane diglycidyl ether (1675-54-3)

Conditions	Yield
With tetramethyl ammoniumhydroxide; dihydrogen peroxide; acetonitrile In methanol; water at 30℃; for 4.5h; pH=11; Product distribution / selectivity;	A 55.2% B 12.6%
With dihydrogen peroxide; acetonitrile; potassium hydroxide In ethanol; water at 30℃; for 4.5h; pH=10.5; Product distribution / selectivity;	A 38.6% B 49.9%
With dihydrogen peroxide; benzonitrile; triethylamine In water at 80℃; for 25h; Conversion of starting material;	A 33% B 8%
Stage #1: bisphenol A diallyl ether; Tri-n-octylamine; sodium tungstate monohydrate; Aminomethylphosphonic acid; sulfuric acid In water; toluene at 80℃; oil bath; Stage #2: With dihydrogen peroxide In water; toluene at 85℃; for 2h; Product distribution / selectivity;

bisphenol A diallyl ether (3739-67-1) → C21H22O3 + C21H20O4

Conditions	Yield
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In cyclohexane; water at 60℃; under 245 - 345 Torr; for 6h; Pressure; Dean-Stark;	A 42% B 20%

bisphenol A diallyl ether (3739-67-1) → bisphenol A monoglycidyl ether (140896-80-6)

Conditions	Yield
With dihydrogen peroxide; acetonitrile; potassium hydroxide In methanol; water at 30℃; for 4.5h; pH=11.5;	25.7%

bisphenol A diallyl ether (3739-67-1) → C21H22O3

Conditions	Yield
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In cyclohexane; water at 60℃; under 760.051 Torr; for 6h; Dean-Stark;	13%

bisphenol A diallyl ether (3739-67-1) → 2,2-bis(3'-n-propyl-4'-hydroxyphenyl)-propane (75672-95-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 4 h / 160 - 180 °C 2: 98 percent / H2 / Pd/C / methanol / 24 h View Scheme
Multi-step reaction with 2 steps 1: 65 percent / various solvent(s) / 5 h / 199.9 - 204.9 °C 2: 87 percent / H2 / 5percent Pd-C / CHCl3 View Scheme

bisphenol A diallyl ether (3739-67-1) → 2,2,14,14-tetramethyl-8,11,17,23-tetrapropyl-6,10,18,22-tetrahydroxycalix[4]arene (188244-21-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / 4 h / 160 - 180 °C 2: 98 percent / H2 / Pd/C / methanol / 24 h 3: 22 percent / BF3*OEt2 / CH2Cl2 / 12 h / Ambient temperature View Scheme

bisphenol A diallyl ether (3739-67-1) → C46H58O4

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / 4 h / 160 - 180 °C 2: 98 percent / H2 / Pd/C / methanol / 24 h 3: 22 percent / BF3*OEt2 / CH2Cl2 / 12 h / Ambient temperature 4: 12 percent / K2CO3 / dimethylformamide / 48 h / Heating View Scheme

bisphenol A diallyl ether (3739-67-1) → C48H60O4

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / 4 h / 160 - 180 °C 2: 98 percent / H2 / Pd/C / methanol / 24 h 3: 22 percent / BF3*OEt2 / CH2Cl2 / 12 h / Ambient temperature 4: 61 percent / K2CO3 / dimethylformamide / 48 h / Heating View Scheme

bisphenol A diallyl ether (3739-67-1) → C21H24O4 (69571-24-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / various solvent(s) / 5 h / 199.9 - 204.9 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 12 h / 59.9 °C View Scheme

bisphenol A diallyl ether (3739-67-1) → 2,2',6,6'-tetraallyl-4,4'-isopropylidenediphenol (71449-73-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / various solvent(s) / 5 h / 199.9 - 204.9 °C 2: 85 percent / NaOH / propan-1-ol / 30 h / Heating 3: 90 percent / 5 h / 199.9 °C View Scheme
Multi-step reaction with 3 steps 1: 1,2-dichloro-benzene / 8 h / 20 - 190 °C 2: potassium carbonate / acetone / 20 - 80 °C 3: 1,2-dichloro-benzene / 8 h / 190 °C View Scheme
Multi-step reaction with 3 steps 1.1: 4 h / 220 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2.2: Reflux; Inert atmosphere 3.1: 4 h / 220 °C / Inert atmosphere View Scheme

bisphenol A diallyl ether (3739-67-1) → 2,2'-bis(2,3-dihydroxypropyl)-4,4'-isopropylidenediphenol (137372-32-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / various solvent(s) / 5 h / 199.9 - 204.9 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 12 h / 59.9 °C 3: aq. NaOH / 24 h / 99.9 °C View Scheme

bisphenol A diallyl ether (3739-67-1) → 4,4’-(dimethylmethylene)bis[2-(2-propenyl)phenyl]diallyl ether (26306-34-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / various solvent(s) / 5 h / 199.9 - 204.9 °C 2: 85 percent / NaOH / propan-1-ol / 30 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 8 h / 20 - 190 °C 2: potassium carbonate / acetone / 20 - 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: 4 h / 220 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2.2: Reflux; Inert atmosphere View Scheme

Upstream product

• 80-05-7 BPA 
• 15022-08-9 diallylcarbonate 
• 107-18-6 allyl alcohol 
• 591-87-7 Allyl acetate 
• 557-40-4 Allyl ether 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 620-92-8 bis-(4-hydroxyphenyl)methane 
• 603-35-0 triphenylphosphine 
• 35466-83-2 allyl methyl carbonate 

Downstream Products

• 1745-89-7 2,2-bis(3-allyl-4-hydroxyphenyl)propane 
• 122165-67-7 4,4'-isopropylidenediphenol dipropyl ether 
• 75672-95-6 2,2-bis(3'-n-propyl-4'-hydroxyphenyl)-propane 
• 69571-24-0 C₂₁H₂₄O₄ 
• 71449-73-5 2,2',6,6'-tetraallyl-4,4'-isopropylidenediphenol 
• 137372-32-8 2,2'-bis(2,3-dihydroxypropyl)-4,4'-isopropylidenediphenol 
• 26306-34-3 4,4’-(dimethylmethylene)bis[2-(2-propenyl)phenyl]diallyl ether 
• 5581-32-8 3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol 
• 13634-08-7 C₁₈H₂₂O₄ 
• 140896-80-6 bisphenol A monoglycidyl ether 
• 1675-54-3 diphenylolpropane diglycidyl ether 
• 80-05-7 BPA 
• 218772-85-1 2,2-bis[3-(3-mercaptopropyl)-4-(3-mercaptopropoxy)phenyl]-propane 
• 1636900-12-3 2,2-bis[3-(3-acetylmercaptopropyl)-4-(3-acetylmercaptopropoxy)-phenyl]propane 

Relevant articles and documents

Kinetic study of synthesizing bisphenol A diallyl ether in a phase-transfer catalytic reaction

In the synthesis of bisphenol A diallyl ether from bisphenol A and allyl bromide, the liquid-liquid mode of operation catalyzed by quaternary ammonium salts was carried out in an alkaline solution/organic solvent two-phase medium. The mono-substituted product was not detected during or after the reaction. In this work, a rational reaction mechanism is proposed and a kinetic model then established. The apparent rate constant of the organic-phase reaction was obtained from experimental data. The effects of the reaction conditions, including agitation speed, organic solvents, quaternary ammonium salts, inorganic salts, temperature, alkali compounds, amount of potassium hydroxide, and water on the conversion of allyl bromide, were investigated in detail. The presence of a small amount of tetrabutylammonium bromide (TBAB) in the chlorobenzene/water system produced a rate over several folds larger than that of the reaction system in the absence of phase-transfer catalyst. The presence of alkali compounds promoted the formation of alkoxide and enhanced the extractive efficiency due to the salting out effect. The present etherification via phase-transfer catalyst could operate at lower temperatures to avoid Claisen rearrangement, which usually occurs at higher temperatures. Rational reasons to account for the absence of mono-substituted product are explained satisfactorily. Peculiar phenomena in investigating the effects of the volume of organic solvent, amount of KOH, and the volume of water and alkali compounds on the apparent rate constants are also explained.

Process for synthesizing diallyl phenol ether compound through azeotropic dehydration

The invention discloses a process for synthesizing a diallyl phenol ether compound by azeotropic dehydration, which comprises the following steps: (1) dissolving a bisphenol compound in an organic solvent, and adding an inorganic base or an aqueous solution of the inorganic base to react to generate phenolate; and (2) vacuumizing the mixture obtained by the reaction in the step (1) or adding a water-carrying agent for dehydration, adding an allyl compound after dehydration is finished, and reacting to obtain the diallyl phenol ether compound. The invention provides a method for preparing a bisphenol compound into an intermediate product phenate and then reacting the intermediate product phenate with a propenyl compound to generate a diallyl phenol ether compound product, which comprises the following steps: adding a water-carrying agent or vacuumizing to remove water in a reaction system; according to the method, the problem of raw material waste caused by hydrolysis of propylene compounds can be effectively avoided, the reaction yield and purity are improved, aftertreatment is simple, and economic benefits are improved.

THERMOSETTING ALKOXYSILYL COMPOUND HAVING TWO OR MORE ALKOXYSILYL GROUPS, COMPOSITION AND CURED PRODUCT COMPRISING SAME, USE THEREOF, AND METHOD FOR PREPARING ALKOXYSILYL COMPOUND

The present invention relates to: a thermosetting alkoxysilyl compound (hereinafter, referred to as “alkoxysilyl compound”)having two or more alkoxysilyl groups showing excellent heat-resistance characteristics in a composite; a composition and a cured product comprising the same; a use thereof; and a method for preparing an alkoxysilyl compound. The composition of an alkoxysilyl compound, comprising a novel alkoxysilyl compound according to the present invention shows, in a composite, improved heat-resistance characteristics, i.e., an effect of decreasing the CTE of the composition of an alkoxysilyl compound and not showing a glass transition temperature (hereinafter, referred to as “Tg-less”). Further, the cured product comprising an alkoxysilyl compound according to the present invention shows excellent flame retardant properties due to the alkoxysilyl groups.