Product Name

  • Name

    Bisphenol A bisallyl ether

  • EINECS 223-123-3
  • CAS No. 3739-67-1
  • Article Data32
  • CAS DataBase
  • Density 1.005 g/cm3
  • Solubility
  • Melting Point
  • Formula C21H24O2
  • Boiling Point 430.5 °C at 760 mmHg
  • Molecular Weight 308.42
  • Flash Point 155.3 °C
  • Transport Information
  • Appearance off-yellow liquid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 3739-67-1 (Bisphenol A bisallyl ether)
  • Hazard Symbols
  • Synonyms Benzene,1,1'-(1-methylethylidene)bis[4-(2-propenyloxy)- (9CI);Propane,2,2-bis[p-(allyloxy)phenyl]- (6CI,7CI,8CI);2,2-Bis(4-allyloxyphenyl)propane;4,4'-Isopropylidenediphenol diallylether;Dial 2;
  • PSA 18.46000
  • LogP 5.14210

Synthetic route

allyl bromide
106-95-6

allyl bromide

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
Stage #1: BPA With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux;
Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;
99%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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;
allyl methyl carbonate
35466-83-2

allyl methyl carbonate

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
Allyl acetate
591-87-7

Allyl acetate

triphenylphosphine
603-35-0

triphenylphosphine

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With sodium hydroxide; palladium diacetate In water95.2%
allyl alcohol
107-18-6

allyl alcohol

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
diallylcarbonate
15022-08-9

diallylcarbonate

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With tetrabutylammomium bromide at 120℃; for 20h; Inert atmosphere;77%
Allyl ether
557-40-4

Allyl ether

A

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol
109348-07-4

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol

B

2,2-bis(3-allyl-4-hydroxyphenyl)propane
1745-89-7

2,2-bis(3-allyl-4-hydroxyphenyl)propane

C

C21H24O2
105577-85-3

C21H24O2

D

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

E

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
allyl alcohol
107-18-6

allyl alcohol

A

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol
109348-07-4

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol

B

2,2-bis(3-allyl-4-hydroxyphenyl)propane
1745-89-7

2,2-bis(3-allyl-4-hydroxyphenyl)propane

C

C21H24O2
105577-85-3

C21H24O2

D

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

E

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
Allyl ether
557-40-4

Allyl ether

A

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

B

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
Allyl acetate
591-87-7

Allyl acetate

A

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol
109348-07-4

2-allyl-4-(2-(4-hydroxyphenyl)propane-2-yl)phenol

B

2,2-bis(3-allyl-4-hydroxyphenyl)propane
1745-89-7

2,2-bis(3-allyl-4-hydroxyphenyl)propane

C

C21H24O2
105577-85-3

C21H24O2

D

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

E

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
allyl alcohol
107-18-6

allyl alcohol

A

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

B

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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%
Allyl acetate
591-87-7

Allyl acetate

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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;
Allyl acetate
591-87-7

Allyl acetate

A

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

B

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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;
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

A

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

B

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With potassium hydroxide In diethylene glycol dimethyl ether; water; dimethyl sulfoxide at 25 - 45℃; for 16h;
allyl methyl carbonate
35466-83-2

allyl methyl carbonate

diallylcarbonate
15022-08-9

diallylcarbonate

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With triphenylphosphine; 5%-palladium/activated carbon at 78℃; for 9.68333h;
bis-(4-hydroxyphenyl)methane
620-92-8

bis-(4-hydroxyphenyl)methane

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
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

methylthiol

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(propane-3,1-diyl))bis(methylsulfane)

(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(propane-3,1-diyl))bis(methylsulfane)

Conditions
ConditionsYield
With C38H28Au2F12FeN2O8P2S4 In 1,4-dioxane at 45℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;99%
bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

4,4'-isopropylidenediphenol dipropyl ether
122165-67-7

4,4'-isopropylidenediphenol dipropyl ether

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In chloroform for 3h;98%
4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol
59501-41-6

4-(2-(4-(allyloxy)phenyl)propane-2-yl)phenol

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

A

C18H22O4
13634-08-7

C18H22O4

B

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol
5581-32-8

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

Conditions
ConditionsYield
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

bisphenol A diallyl ether

2,2-bis(3-allyl-4-hydroxyphenyl)propane
1745-89-7

2,2-bis(3-allyl-4-hydroxyphenyl)propane

Conditions
ConditionsYield
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

bisphenol A diallyl ether

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol
5581-32-8

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

Conditions
ConditionsYield
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 diallyl ether

A

bisphenol A monoglycidyl ether
140896-80-6

bisphenol A monoglycidyl ether

B

diphenylolpropane diglycidyl ether
1675-54-3

diphenylolpropane diglycidyl ether

Conditions
ConditionsYield
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

bisphenol A diallyl ether

A

C21H22O3

C21H22O3

B

C21H20O4

C21H20O4

Conditions
ConditionsYield
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 diallyl ether

bisphenol A monoglycidyl ether
140896-80-6

bisphenol A monoglycidyl ether

Conditions
ConditionsYield
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

bisphenol A diallyl ether

C21H22O3

C21H22O3

Conditions
ConditionsYield
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

bisphenol A diallyl ether

2,2-bis(3'-n-propyl-4'-hydroxyphenyl)-propane
75672-95-6

2,2-bis(3'-n-propyl-4'-hydroxyphenyl)-propane

Conditions
ConditionsYield
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

bisphenol A diallyl ether

2,2,14,14-tetramethyl-8,11,17,23-tetrapropyl-6,10,18,22-tetrahydroxycalix[4]arene
188244-21-5

2,2,14,14-tetramethyl-8,11,17,23-tetrapropyl-6,10,18,22-tetrahydroxycalix[4]arene

Conditions
ConditionsYield
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

bisphenol A diallyl ether

C46H58O4

C46H58O4

Conditions
ConditionsYield
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

bisphenol A diallyl ether

C48H60O4

C48H60O4

Conditions
ConditionsYield
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

bisphenol A diallyl ether

C21H24O4
69571-24-0

C21H24O4

Conditions
ConditionsYield
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

bisphenol A diallyl ether

2,2',6,6'-tetraallyl-4,4'-isopropylidenediphenol
71449-73-5

2,2',6,6'-tetraallyl-4,4'-isopropylidenediphenol

Conditions
ConditionsYield
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

bisphenol A diallyl ether

2,2'-bis(2,3-dihydroxypropyl)-4,4'-isopropylidenediphenol
137372-32-8

2,2'-bis(2,3-dihydroxypropyl)-4,4'-isopropylidenediphenol

Conditions
ConditionsYield
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

bisphenol A diallyl ether

4,4’-(dimethylmethylene)bis[2-(2-propenyl)phenyl]diallyl ether
26306-34-3

4,4’-(dimethylmethylene)bis[2-(2-propenyl)phenyl]diallyl ether

Conditions
ConditionsYield
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

Bisphenol A bisallyl ether Specification

The Bisphenol A bisallyl ether with the cas number 3739-67-1, is also called 2,2-Bis(4-allyloxyphenyl)propane.The product can be supplied by the following suppliers: (1)Laizhou Laiyu Chemical Co., Ltd.; (2)Sichuan Huishuo Chemical Co., Ltd.; (3)Waterstone Technology, LLC.; (4)Aagile Labs Division of Tyger Scientific; (5)MOLEKULA Ltd.; (6)Nanjing Chemlin Chemical Co., Ltd..

The properties of the chemical are: (1)ACD/LogP: 6.35; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.35; (4)ACD/LogD (pH 7.4): 6.35; (5)ACD/BCF (pH 5.5): 39130.04; (6)ACD/BCF (pH 7.4): 39130.04; (7)ACD/KOC (pH 5.5): 67437.63; (8)ACD/KOC (pH 7.4): 67437.63; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 95.74 cm3; (15)Molar Volume: 306.9 cm3; (16)Polarizability: 37.95×10-24cm3; (17)Surface Tension: 33.8 dyne/cm; (18)Enthalpy of Vaporization: 65.94 kJ/mol; (19)Vapour Pressure: 3.25×10-7 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccc(cc1)C(c1ccc(OCC=C)cc1)(C)C)CC=C
(2)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

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