Product Name

  • Name

    4-Vinylbenzyl chloride

  • EINECS 216-471-2
  • CAS No. 1592-20-7
  • Article Data18
  • CAS DataBase
  • Density 1.066 g/cm3
  • Solubility Insoluble in water
  • Melting Point
  • Formula C9H9Cl
  • Boiling Point 228.9 °C at 760 mmHg
  • Molecular Weight 152.623
  • Flash Point 90.4 °C
  • Transport Information UN 3265 8/PG 3
  • Appearance clear yellow liquid
  • Safety 26-36/37/39-45
  • Risk Codes 34-43-21/22
  • Molecular Structure Molecular Structure of 1592-20-7 (4-Vinylbenzyl chloride)
  • Hazard Symbols CorrosiveC
  • Synonyms Styrene,p-(chloromethyl)- (6CI,7CI,8CI);1-(Chloromethyl)-4-vinylbenzene;4-(Chloromethyl)styrene;CMS 14;p-(Chloromethyl)styrene;p-Vinylbenzyl chloride;
  • PSA 0.00000
  • LogP 3.06840

Synthetic route

p-chloromethyl-α-bromoethylbenzene
35793-35-2

p-chloromethyl-α-bromoethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With 18-crown-6 ether; potassium hydroxide In toluene at 40℃; for 4h; Reagent/catalyst; Temperature; Solvent;95%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; Tropone In dichloromethane at 20℃; for 0.25h; Inert atmosphere;84%
1-(2-chloroethyl)-4-(chloromethyl)benzene
53459-40-8

1-(2-chloroethyl)-4-(chloromethyl)benzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With 4-tert-Butylcatechol; sodium t-butanolate In tetrahydrofuran at 30℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere;83%
p-chloromethyl-2-bromoethylbenzene
24249-98-7

p-chloromethyl-2-bromoethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide at 30℃; for 4h; different reagents, solvents and reaction times;77%
With tetrabutylammomium bromide; potassium hydroxide In tert-butyl alcohol at 30℃; for 4h;50.1%
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In fluorobenzene; water at 20℃; Irradiation; Green chemistry;68%
poly 4-chlorostyrene

poly 4-chlorostyrene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
at 500 - 650℃;60%
styrene
292638-84-7

styrene

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With carbon disulfide; zinc(II) chloride at 40℃; for 5h; Reflux;13%
4-ethylbenzylchloride
1467-05-6

4-ethylbenzylchloride

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
(i) NBS, (PhCO)2O2, (ii) (heating), benzene-1,4-diol; Multistep reaction;
1-(4-chloromethylphenyl)ethanol
76297-21-7

1-(4-chloromethylphenyl)ethanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With potassium hydrogensulfate; 4-tert-Butylcatechol at 210℃;
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

A

α-chloro-p-methylstyrene
42107-37-9

α-chloro-p-methylstyrene

B

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

C

di- and trichlorinated products

di- and trichlorinated products

Conditions
ConditionsYield
With chlorine In water at 560℃; for 0.000222222h; Product distribution; gas phase reaction, oth. isomers;
4-chloromethylbenzaldehyde
73291-09-5

4-chloromethylbenzaldehyde

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: KHSO4, 4-tert-butyl-benzene-1,2-diol / 210 °C
View Scheme
4-chloromethylbenzaldehyde
73291-09-5

4-chloromethylbenzaldehyde

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 16h; Wittig Olefination;
ethylbenzene
100-41-4

ethylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine / 3 h / Reflux; Inert atmosphere
2: hydrogenchloride; zinc(II) chloride / 20 h / 40 °C / Reflux
3: potassium hydroxide; 18-crown-6 ether / toluene / 4 h / 40 °C
View Scheme
2-phenylethanol
60-12-8

2-phenylethanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen bromide; zinc(II) chloride / 6 h / 80 - 90 °C / Reflux
2: hydrogenchloride; zinc(II) chloride / 18 h / 30 °C / Reflux
3: tetrabutylammomium bromide; potassium hydroxide / tert-butyl alcohol / 4 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 8 h / 120 °C
2: hydrogenchloride; sulfuric acid; zinc(II) chloride / water / 5 h / 90 °C
3: sodium t-butanolate; 4-tert-Butylcatechol / tetrahydrofuran / 1 h / 30 °C / Inert atmosphere
View Scheme
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; zinc(II) chloride / 18 h / 30 °C / Reflux
2: tetrabutylammomium bromide; potassium hydroxide / tert-butyl alcohol / 4 h / 30 °C
View Scheme
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

1,2-dibromo-1-(4-chlorophenyl)ethane

1,2-dibromo-1-(4-chlorophenyl)ethane

Conditions
ConditionsYield
With Ph-HMS; bromine In dichloromethane for 5h; Ambient temperature; Irradiation;100%
With sodium periodate; acetic acid; lithium bromide at 25℃;96%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

2-bromo-1-(4-chloromethylphenyl)ethanol

2-bromo-1-(4-chloromethylphenyl)ethanol

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetonitrile at 20℃;100%
With sodium periodate; sulfuric acid; lithium bromide In water; acetonitrile at 25℃; pH=6.12;85%
With N-Bromosuccinimide; water In acetone at 0 - 20℃;
pyrrolidine
123-75-1

pyrrolidine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

1-[(4-ethenylphenyl)methyl]-pyrrolidine
60472-54-0

1-[(4-ethenylphenyl)methyl]-pyrrolidine

Conditions
ConditionsYield
In hexane at 0 - 20℃;100%
In hexane at 20℃; for 20h; Cooling with ice;98%
In hexane at 0 - 20℃;
In hexane
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

dimethylamino-methanesulfonic acid ; sodium salt

dimethylamino-methanesulfonic acid ; sodium salt

4-vinylbenzyldimethylammonio methanesulfonate
1273544-34-5

4-vinylbenzyldimethylammonio methanesulfonate

Conditions
ConditionsYield
In ethanol; water at 45℃; for 24h; Inert atmosphere;100%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

trimethylamine
75-50-3

trimethylamine

N,N,N-trimethyl-1-(4-vinylphenyl)methanaminium chloride
7538-38-7

N,N,N-trimethyl-1-(4-vinylphenyl)methanaminium chloride

Conditions
ConditionsYield
In ethanol at 20℃; for 18h;100%
In water at 0℃; for 72h;
In N,N-dimethyl-formamide at 60℃; for 24h; Autoclave;
bis-(dimethylamino)methane
51-80-9

bis-(dimethylamino)methane

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

Conditions
ConditionsYield
In acetonitrile at 50℃; for 48h; Inert atmosphere;100%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

sodium acetate
127-09-3

sodium acetate

4-acetoxymethylstyrene
1592-12-7

4-acetoxymethylstyrene

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 48h; Heating;99%
In dimethyl sulfoxide at 50℃; for 47h;
In dimethyl sulfoxide at 45℃; for 24h; Inert atmosphere;
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

4-vinylbenzyl iodide
45817-37-6

4-vinylbenzyl iodide

Conditions
ConditionsYield
With sodium iodide In acetone for 20h; Inert atmosphere; Reflux;99%
With sodium iodide In acetonitrile for 12h; Inert atmosphere; Reflux;92%
With sodium iodide In butanone at 20℃; for 8h;91%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

triethylamine
121-44-8

triethylamine

triethyl-(4-vinylbenzyl)ammonium chloride
14350-43-7

triethyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In methanol at 30℃;99%
In acetonitrile at 40℃; for 93h;94%
With 2,6-di-tert-butyl-4-methyl-phenol at 50℃; for 48h; Inert atmosphere;
In N,N-dimethyl-formamide at 60℃; for 24h; Autoclave;
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

trioctyl(4-vinylbenzyl)phosphonium chloride

trioctyl(4-vinylbenzyl)phosphonium chloride

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;99%
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;
tributyl-amine
102-82-9

tributyl-amine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

tri-n-butyl-(4-vinylbenzyl)ammonium chloride

tri-n-butyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In acetonitrile at 40℃; for 68h;99%
In dichloromethane at 20℃; for 48h;85%
In acetonitrile at 50℃; for 48h;82%
In acetonitrile at 40℃; for 24h; Inert atmosphere;80%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

C16H16Cl2O2S

C16H16Cl2O2S

Conditions
ConditionsYield
With [Cu(2,9-bis(p-anisyl)-1,10-phenanthroline)Cl2] In acetonitrile at 25 - 30℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; regioselective reaction;99%
N,N-dimethyldecylamine
1120-24-7

N,N-dimethyldecylamine

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

decyldimethyl-(4-vinylbenzyl)ammonium chloride

decyldimethyl-(4-vinylbenzyl)ammonium chloride

Conditions
ConditionsYield
In acetonitrile at 40℃; for 239h;99%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

potassium phtalimide
1074-82-4

potassium phtalimide

2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione
63413-74-1

2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide98%
In N,N-dimethyl-formamide at 110℃; for 5h;88%
In N,N-dimethyl-formamide at 55℃; for 17h;81%
styrene
292638-84-7

styrene

1,4-Divinylbenzene
105-06-6

1,4-Divinylbenzene

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

polymer; Monomer(s): styrene; 4-chloromethylstyrene; 1,4-divinylbenzene

polymer; Monomer(s): styrene; 4-chloromethylstyrene; 1,4-divinylbenzene

Conditions
ConditionsYield
With dibenzoyl peroxide at 80℃; for 24h;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide; water at 125℃; for 0.333333h;98%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 125℃; for 0.666667h;95%
With tetrabutylammomium bromide; sodium hydroxide In water at 125℃; for 2h; Inert atmosphere;57%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

phenyltriisopropoxytitanium(IV)
16635-23-7

phenyltriisopropoxytitanium(IV)

phenyl(p-vinylphenyl)methane
15866-31-6

phenyl(p-vinylphenyl)methane

Conditions
ConditionsYield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 25℃; for 2h; Inert atmosphere;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

undecyl 4'-hydroxybiphenyl-4-carboxylate
132328-89-3

undecyl 4'-hydroxybiphenyl-4-carboxylate

undecyl 4'-(4-vinylbenzyloxy)biphenyl-4-carboxylate
1104078-17-2

undecyl 4'-(4-vinylbenzyloxy)biphenyl-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 8h;98%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-(4-vinyl-benzylsulfanyl)-ethanol
129509-07-5

2-(4-vinyl-benzylsulfanyl)-ethanol

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide In tetrahydrofuran; water Reflux;98%
1H-imidazole
288-32-4

1H-imidazole

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

1-(4-vinylbenzyl)-1H-imidazole
78430-91-8

1-(4-vinylbenzyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydroxide In tetrahydrofuran for 2h; Reflux;
Stage #2: 4-Vinylbenzyl chloride In tetrahydrofuran at 20℃;
98%
With sodium hydrogencarbonate In water; acetone at 20 - 50℃; for 20h;71%
With sodium hydrogencarbonate In acetonitrile at 50℃; for 20h;71%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

propargyl alcohol
107-19-7

propargyl alcohol

1-((prop-2-yn-1-yloxy)methyl)-4-vinylbenzene
132679-16-4

1-((prop-2-yn-1-yloxy)methyl)-4-vinylbenzene

Conditions
ConditionsYield
Stage #1: propargyl alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h;
Stage #2: 4-Vinylbenzyl chloride With tetra-(n-butyl)ammonium iodide for 12h; Reflux;
98%
Stage #1: propargyl alcohol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-Vinylbenzyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;
71%
Stage #1: propargyl alcohol With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice;
Stage #2: 4-Vinylbenzyl chloride With tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 5h;
59%

4-Vinylbenzyl chloride Chemical Properties

IUPAC Name: 1-(Chloromethyl)-4-ethenylbenzene
Synonyms of Benzene,1-(chloromethyl)-4-ethenyl- (CAS NO.1592-20-7): EINECS 216-471-2 ; 1-(Chloromethyl)-4-vinylbenzene
CAS NO: 1592-20-7
Molecular Formula: C9H9Cl
Molecular Weight: 152.6208
Molecular Structure:
 
ProductCategories: Intermediates of Dyes and Pigments 
Index of Refraction: 1.57
Molar Refractivity: 46.94 cm3
Molar Volume: 143 cm3
Surface Tension: 34.7 dyne/cm
Density of Benzene,1-(chloromethyl)-4-ethenyl- (CAS NO.1592-20-7): 1.066 g/cm3
Flash Point: 90.4 °C
Enthalpy of Vaporization: 44.66 kJ/mol
Boiling Point: 228.9 °C at 760 mmHg
Vapour Pressure: 0.108 mmHg at 25°C

4-Vinylbenzyl chloride Safety Profile

Hazard Codes of Benzene,1-(chloromethyl)-4-ethenyl- (CAS NO.1592-20-7): CorrosiveC
Risk Statements: 34-43-21/22 
R34: Causes burns. 
R43: May cause sensitization by skin contact. 
R21/22: Harmful in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-45 
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. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 3
WGK Germany: 3
F: 8-19
HazardClass: 8
PackingGroup: III

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