Product Name

  • Name

    1,4-DIISOPROPENYLBENZENE

  • EINECS
  • CAS No. 1605-18-1
  • Article Data14
  • CAS DataBase
  • Density 0.873g/cm3
  • Solubility
  • Melting Point 65oC
  • Formula C12H14
  • Boiling Point 239.9°Cat760mmHg
  • Molecular Weight 158.243
  • Flash Point 93.3°C
  • Transport Information
  • Appearance
  • Safety Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes R36/37/38
  • Molecular Structure Molecular Structure of 1605-18-1 (1,4-DIISOPROPENYLBENZENE)
  • Hazard Symbols
  • Synonyms Benzene,p-diisopropenyl- (6CI,7CI,8CI); 1,4-Bis(1-methylvinyl)benzene;1,4-Diisopropenylbenzene; NSC 84197; p-Diisopropenylbenzene
  • PSA 0.00000
  • LogP 3.75280

Synthetic route

4-chlorocarbonylbenzoic acid phenyl ester
25061-09-0

4-chlorocarbonylbenzoic acid phenyl ester

trimethylaluminum
75-24-1

trimethylaluminum

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;90%
α,α,α',α'-tetramethyl-1,4-benzenedimethanol
2948-46-1

α,α,α',α'-tetramethyl-1,4-benzenedimethanol

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 110℃; Dean-Stark;87%
With potassium hydrogensulfate at 150 - 160℃; durch Destillation unter vermindertem Druck;
Multi-step reaction with 2 steps
1: benzene; hydrogen chloride
2: pyridine
View Scheme
trimethylaluminum
75-24-1

trimethylaluminum

terephthaloyl chloride
100-20-9

terephthaloyl chloride

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;82%
4-chlorophenyl methyl sulfide
123-09-1

4-chlorophenyl methyl sulfide

isopropenylmagnesium bromide
13291-18-4

isopropenylmagnesium bromide

A

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

B

methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

C

methyl (4-(prop-1-en-2-yl)phenyl)sulfane
74362-50-8

methyl (4-(prop-1-en-2-yl)phenyl)sulfane

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In benzene at 25℃; for 5h;A 25%
B n/a
C 50%
4-chlorophenyl methyl sulfide
123-09-1

4-chlorophenyl methyl sulfide

isopropenylmagnesium bromide
13291-18-4

isopropenylmagnesium bromide

A

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

B

methyl (4-(prop-1-en-2-yl)phenyl)sulfane
74362-50-8

methyl (4-(prop-1-en-2-yl)phenyl)sulfane

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In benzene at 25℃; for 5h;A 25%
B 50%
4-chlorophenyl methyl sulfide
123-09-1

4-chlorophenyl methyl sulfide

allylmagnesium bromide
1730-25-2

allylmagnesium bromide

A

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

B

methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

C

1-(methylsulfanyl)-4-(prop-2-en-1-yl)benzene
59209-68-6

1-(methylsulfanyl)-4-(prop-2-en-1-yl)benzene

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In benzene at 25℃; for 6h;A 25%
B n/a
C 35%
1,4-bis(1-methylethyl)benzene
100-18-5

1,4-bis(1-methylethyl)benzene

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
at 625℃; Leiten ueber Kupferchromit;
at 625℃; Leiten ueber Kupfer-Chrom(III)-oxyd;
α,α,α',α'-tetramethyl-1,4-benzene dimethylchloride
7374-80-3

α,α,α',α'-tetramethyl-1,4-benzene dimethylchloride

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
With pyridine
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

isopropenylmagnesium bromide
13291-18-4

isopropenylmagnesium bromide

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
nickel
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
In dimethyl sulfoxide
α,α,α',α'-tetramethyl-1,4-benzenedimethanol
2948-46-1

α,α,α',α'-tetramethyl-1,4-benzenedimethanol

KHSO4

KHSO4

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
at 150 - 160℃; unter vermindertem Druck;
4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

C7H14MgO

C7H14MgO

A

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

B

2-(4-fluorophenyl)-1-propene
350-40-3

2-(4-fluorophenyl)-1-propene

Conditions
ConditionsYield
With Tridecane; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 60℃;A 5 % Chromat.
B 46 % Chromat.
para-dichlorobenzene
106-46-7

para-dichlorobenzene

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 25 percent / Ni(PPh3)2Cl2 / benzene / 5 h / 25 °C
View Scheme
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: KHSO4 / 150 - 160 °C / durch Destillation unter vermindertem Druck
View Scheme
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

N-methylaniline
100-61-8

N-methylaniline

α.α'-Bis-<(4-Methylamino)-phenyl>-α.α.α'.α'-tetramethyl-p-xylol
2716-13-4

α.α'-Bis-<(4-Methylamino)-phenyl>-α.α.α'.α'-tetramethyl-p-xylol

Conditions
ConditionsYield
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 36h; Inert atmosphere; chemoselective reaction;89%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

C20H25N

C20H25N

Conditions
ConditionsYield
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 28h; Inert atmosphere; regioselective reaction;81%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

C28H36N2

C28H36N2

Conditions
ConditionsYield
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 36h; Inert atmosphere; regioselective reaction;78%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;78%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

α-methoxycarbonylmaleic anhydride
69327-00-0

α-methoxycarbonylmaleic anhydride

4,5-Dicarbomethoxy-2,3,4,4a,5a,5,6,7-octahydro-1,8-dimethylphenanthrene-3,4,5,6-tetracarboxylic Acid Dianhydride
134815-55-7

4,5-Dicarbomethoxy-2,3,4,4a,5a,5,6,7-octahydro-1,8-dimethylphenanthrene-3,4,5,6-tetracarboxylic Acid Dianhydride

Conditions
ConditionsYield
In diethyl ether at 28℃; for 0.0333333h;73%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

9-Bromoanthracene
1564-64-3

9-Bromoanthracene

1,4-bis((E)-1-(anthracen-9-yl)prop-1-en-2-yl)benzene
1195237-59-2

1,4-bis((E)-1-(anthracen-9-yl)prop-1-en-2-yl)benzene

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 48h; Heck reaction; Inert atmosphere; regioselective reaction;70%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1,4-bis((E)-1-(naphthalen-1-yl)prop-1-en-2-yl)benzene
1195237-56-9

1,4-bis((E)-1-(naphthalen-1-yl)prop-1-en-2-yl)benzene

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 60h; Heck reaction; Inert atmosphere; regioselective reaction;66%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C18H25BO2

C18H25BO2

Conditions
ConditionsYield
With tetrakis(trimethylphosphine)iron(0); norbornene In hexane at 50℃; for 18h; stereoselective reaction;62%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

4-nitrobenzenediazonium tetrafluoroborate
456-27-9

4-nitrobenzenediazonium tetrafluoroborate

1-(4-nitrophenyl)-2-(3-(prop-1-en-2-yl)phenyl)propan-2-ol

1-(4-nitrophenyl)-2-(3-(prop-1-en-2-yl)phenyl)propan-2-ol

Conditions
ConditionsYield
With water at 20℃; for 4h; Meerwein Arylation; Schlenk technique; Irradiation; Inert atmosphere; Green chemistry;62%
methanol
67-56-1

methanol

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

1-(1,2-dimethoxypropan-2-yl)-4-(prop-1-en-2-yl)benzene

1-(1,2-dimethoxypropan-2-yl)-4-(prop-1-en-2-yl)benzene

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 60℃; for 2h; Inert atmosphere; Electrolysis;44%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

dithiobenzoic acid
121-68-6

dithiobenzoic acid

1,4-bis(2-(thiobenzoylthio)prop-2-yl)benzene
201611-82-7

1,4-bis(2-(thiobenzoylthio)prop-2-yl)benzene

Conditions
ConditionsYield
In tetrachloromethane at 75℃; for 20h;41.1%
In tetrachloromethane24.6%
With toluene-4-sulfonic acid
In tetrachloromethane at 75℃; for 20h;
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione
1087053-43-7

6-bromo-2-cetyl-1H-benzo[de]isoquinoline-1,3-(2H)-dione

A

4,4',2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N-hexadecyl-1,8-naphthalimide)

4,4',2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N-hexadecyl-1,8-naphthalimide)

B

4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N-hexadecyl-1,8-naphthalimide)
1195237-62-7

4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N-hexadecyl-1,8-naphthalimide)

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 48h; Heck reaction; Inert atmosphere;A n/a
B 28%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

1,1,2,2-Tetracyano-3-methyl-3-(p-isopropenylphenyl)cyclobutane
129534-35-6

1,1,2,2-Tetracyano-3-methyl-3-(p-isopropenylphenyl)cyclobutane

Conditions
ConditionsYield
In acetonitrile at 28℃;25%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

A

4,4',2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N,N-diphenylaniline)
164257-41-4

4,4',2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N,N-diphenylaniline)

B

4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N,N-diphenylaniline)
1195237-68-3

4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(prop-1-ene-2,1-diyl)bis(N,N-diphenylaniline)

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 48h; Heck reaction; Inert atmosphere;A n/a
B 22%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

2-bromo-9,9-dimethyl-9H-fluorene
28320-31-2

2-bromo-9,9-dimethyl-9H-fluorene

A

1,4-bis(1-(9,9-dimethyl-9H-fluoren-2-yl)prop-1-en-2-yl)benzene

1,4-bis(1-(9,9-dimethyl-9H-fluoren-2-yl)prop-1-en-2-yl)benzene

B

1,4-bis((E)-1-(9,9-dimethyl-9H-fluoren-2-yl)prop-1-en-2-yl)benzene
1195237-66-1

1,4-bis((E)-1-(9,9-dimethyl-9H-fluoren-2-yl)prop-1-en-2-yl)benzene

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 48h; Heck reaction; Inert atmosphere;A n/a
B 14%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

Methyl β,β-dicyanoacrylate
82849-50-1

Methyl β,β-dicyanoacrylate

Dimethyl 4,4,5,5-Tetracyano-2,3,4,4a,5a,5,6,7-octahydro-1,8-dimethylphenanthrene-3,6-dicarboxylate
134782-11-9

Dimethyl 4,4,5,5-Tetracyano-2,3,4,4a,5a,5,6,7-octahydro-1,8-dimethylphenanthrene-3,6-dicarboxylate

Conditions
ConditionsYield
In acetonitrile at 28℃; for 120h;10%
1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

1-bromopyrene
1714-29-0

1-bromopyrene

A

1,4-bis(1-(pyren-1-yl)prop-1-en-2-yl)benzene

1,4-bis(1-(pyren-1-yl)prop-1-en-2-yl)benzene

B

1,4-bis((E)-1-(pyren-1-yl)prop-1-en-2-yl)benzene
1195237-64-9

1,4-bis((E)-1-(pyren-1-yl)prop-1-en-2-yl)benzene

Conditions
ConditionsYield
With bis(tri-tert-butylphosphine)palladium(0); dicyclohexylmethylamine In toluene at 100℃; for 24h; Heck reaction; Inert atmosphere;A n/a
B 8%
dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

A

Ru2*6CO*C12H16 = [Ru2(CO)6(C12H16)]

Ru2*6CO*C12H16 = [Ru2(CO)6(C12H16)]

B

Ru2*6CO*C12H14 = [Ru2(CO)6(C12H14)]

Ru2*6CO*C12H14 = [Ru2(CO)6(C12H14)]

C

Ru3H*9CO*C12H11 = [Ru3H(CO)9(C12H11)]

Ru3H*9CO*C12H11 = [Ru3H(CO)9(C12H11)]

D

Ru7C*16CO*C12H12 = [Ru7C(CO)16(C12H12)]

Ru7C*16CO*C12H12 = [Ru7C(CO)16(C12H12)]

E

[Ru4(CO)10(C12H14)]

[Ru4(CO)10(C12H14)]

Conditions
ConditionsYield
In octane (N2); reflux (2 h); further products; solvent removal, TLC (eluent; hexane/CH2Cl2), not all complexes could beseparated, but characterized by spectr. means;A n/a
B n/a
C 4%
D 2.9%
E 1.8%
dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

A

Ru6C*15CO*C11H10 = [Ru6C(CO)15(C11H10)]

Ru6C*15CO*C11H10 = [Ru6C(CO)15(C11H10)]

B

Ru5H*14CO*C12H11 = [Ru5H(CO)14(C12H11)]

Ru5H*14CO*C12H11 = [Ru5H(CO)14(C12H11)]

C

[Ru4(CO)10(C12H14)]

[Ru4(CO)10(C12H14)]

Conditions
ConditionsYield
In octane (N2); reflux (2 h); further products; solvent removal, TLC (eluent; hexane/CH2Cl2), not all complexes could beseparated, but characterized by spectr. means;A 0.7%
B 2.2%
C 1.8%
dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

1,4-diisopropenyl-benzene
1605-18-1

1,4-diisopropenyl-benzene

A

[Ru6H(CO)15(C12H11)]

[Ru6H(CO)15(C12H11)]

B

[Ru6H(CO)15(C12H13)]

[Ru6H(CO)15(C12H13)]

C

[Ru3(CO)8(C12H14)]

[Ru3(CO)8(C12H14)]

D

[Ru3(CO)8(C12H12)]

[Ru3(CO)8(C12H12)]

E

[Ru4(CO)10(C12H14)]

[Ru4(CO)10(C12H14)]

Conditions
ConditionsYield
In octane (N2); reflux (2 h); further products; solvent removal, TLC (eluent; hexane/CH2Cl2), not all complexes could beseparated, but characterized by spectr. means;A n/a
B n/a
C n/a
D n/a
E 1.8%

p-Isopropenyl-α-methylstyrene Chemical Properties

IUPAC Name: 1,4-bis(Prop-1-en-2-yl)benzene
Synonyms: 1,4-Diisopropenylbenzene ; 1,4-Bis(1-Methylethenyl)benzene ; 1,4-Bis(1-methylvinyl)benzene ; 1,4-Diisopropenylbenzene
Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research
CAS NO: 1605-18-1
Molecular Formula of p-Isopropenyl-α-methylstyrene (CAS NO.1605-18-1) : C12H14
Molecular Weight of p-Isopropenyl-α-methylstyrene (CAS NO.1605-18-1) : 158.24
Molecular structure of p-Isopropenyl-α-methylstyrene (CAS NO.1605-18-1) :
EINECS: 216-515-0
Index of Refraction: 1.515
Surface Tension: 28.2 dyne/cm
Density: 0.873 g/cm3
Flash Point: 93.3 °C
Enthalpy of Vaporization: 45.74 kJ/mol
Boiling Point: 239.9 °C at 760 mmHg
Vapour Pressure: 0.0606 mmHg at 25°C
Melting point: 65°C

p-Isopropenyl-α-methylstyrene History

p-Isopropenyl-α-methylstyrene Toxicity Data With Reference

1.    

orl-rat LD:>10 mL/kg

    AMIHAB    AMA Archives of Industrial Health. 19 (1959),403.

p-Isopropenyl-α-methylstyrene Consensus Reports

Reported in EPA TSCA Inventory.

p-Isopropenyl-α-methylstyrene Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RTECS CY8536000

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