1592-20-7

Basic information

• Product Name: 4-Vinylbenzyl chloride
• Synonyms: 1-(chloromethyl)-4-ethenyl-benzen;1-(chloromethyl)-4-ethenyl-Benzene;4-(CHLOROMETHYL)STYRENE;4-VINYLBENZYL CHLORIDE;1-(chloromethyl)-4-vinylbenzene;4-VINYLBENZYL CHLORIDE, STAB.;4-Vinylbenylchloride;4-Vinylbenzyl chloride, tech., 90%
• CAS NO: 1592-20-7
• Molecular Formula: C₉H₉Cl
• Molecular Weight: 152.62
• EINECS: 250-005-9
• Product Categories: Intermediates of Dyes and Pigments;Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Chloromethy styrene
• Mol File: 1592-20-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 229 °C(lit.)
• Flash Point: 221 °F
• Appearance: Clear yellow/Liquid
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Density: 5.3 (vs air)
• Vapor Pressure: 1 mm Hg ( 56.1 °C)
• Refractive Index: n20/D 1.572(lit.)
• Storage Temp.: −20°C
• Water Solubility: Insoluble in water
• BRN: 2204384
• CAS DataBase Reference: 4-Vinylbenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Vinylbenzyl chloride(1592-20-7)
• EPA Substance Registry System: 4-Vinylbenzyl chloride(1592-20-7)

Safety Data

• Hazard Codes: C
• Statements: 34-43-21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• F: 8-19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1592-20-7(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

Component of ion exchange resins, photo-resist polymers, cross-linkable fibers, coupling agents and electroconducting polymers.Starter for various copolymer preparations.Dual functional monomer. Readily derivatized by chloride displacement.

Purification Methods

Purify 4-vinylbenzyl chloride by dissolving it in Et2O, washing it with 0.5% of aqueous NaOH, separating, drying the organic layer (Na2SO4), evaporating and distilling the residual oil under N2 in vacuo. Add 0.05% of 4-tert-butylcatechol as stabilizer. It is lachrymatory. [Nishikubo et al. Tetrahedron Lett 22 3872 1981, Tanimoto et al. Synth Commun 4 193 1974, Beilstein 6 IV 3818.]

InChI:InChI=1/C9H9Cl/c1-2-8-3-5-9(7-10)6-4-8/h2-6H,1,7H2

Synthetic route

p-chloromethyl-α-bromoethylbenzene (35793-35-2) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
With oxalyl dichloride; Tropone In dichloromethane at 20℃; for 0.25h; Inert atmosphere;	84%

1-(2-chloroethyl)-4-(chloromethyl)benzene (53459-40-8) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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) → 4-Vinylbenzyl chloride (1592-20-7)

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

poly 4-chlorostyrene → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
at 500 - 650℃;	60%

styrene (292638-84-7) + chloromethyl methyl ether (107-30-2) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
With carbon disulfide; zinc(II) chloride at 40℃; for 5h; Reflux;	13%

4-ethylbenzylchloride (1467-05-6) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
(i) NBS, (PhCO)2O2, (ii) (heating), benzene-1,4-diol; Multistep reaction;

1-(4-chloromethylphenyl)ethanol (76297-21-7) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
With potassium hydrogensulfate; 4-tert-Butylcatechol at 210℃;

1-ethenyl-4-methylbenzene (622-97-9) → α-chloro-p-methylstyrene (42107-37-9) + 4-Vinylbenzyl chloride (1592-20-7) + di- and trichlorinated products

Conditions	Yield
With chlorine In water at 560℃; for 0.000222222h; Product distribution; gas phase reaction, oth. isomers;

4-chloromethylbenzaldehyde (73291-09-5) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: KHSO4, 4-tert-butyl-benzene-1,2-diol / 210 °C View Scheme

4-chloromethylbenzaldehyde (73291-09-5) + Methyltriphenylphosphonium bromide (1779-49-3) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 16h; Wittig Olefination;

ethylbenzene (100-41-4) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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) → 4-Vinylbenzyl chloride (1592-20-7)

Conditions	Yield
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) → 1,2-dibromo-1-(4-chlorophenyl)ethane

Conditions	Yield
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) → 2-bromo-1-(4-chloromethylphenyl)ethanol

Conditions	Yield
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) + 4-Vinylbenzyl chloride (1592-20-7) → 1-[(4-ethenylphenyl)methyl]-pyrrolidine (60472-54-0)

Conditions	Yield
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) + dimethylamino-methanesulfonic acid ; sodium salt → 4-vinylbenzyldimethylammonio methanesulfonate (1273544-34-5)

Conditions	Yield
In ethanol; water at 45℃; for 24h; Inert atmosphere;	100%

4-Vinylbenzyl chloride (1592-20-7) + trimethylamine (75-50-3) → N,N,N-trimethyl-1-(4-vinylphenyl)methanaminium chloride (7538-38-7)

Conditions	Yield
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) + 4-Vinylbenzyl chloride (1592-20-7) → N,N'-(methylene)bis(N,N-dimethyl-1-(4-vinylphenyl)methanaminium) chloride

Conditions	Yield
In acetonitrile at 50℃; for 48h; Inert atmosphere;	100%

4-Vinylbenzyl chloride (1592-20-7) + sodium acetate (127-09-3) → 4-acetoxymethylstyrene (1592-12-7)

Conditions	Yield
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 iodide (45817-37-6)

Conditions	Yield
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) + triethylamine (121-44-8) → triethyl-(4-vinylbenzyl)ammonium chloride (14350-43-7)

Conditions	Yield
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;

TOP (4731-53-7) + 4-Vinylbenzyl chloride (1592-20-7) → trioctyl(4-vinylbenzyl)phosphonium chloride

Conditions	Yield
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) + 4-Vinylbenzyl chloride (1592-20-7) → tri-n-butyl-(4-vinylbenzyl)ammonium chloride

Conditions	Yield
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) + p-toluenesulfonyl chloride (98-59-9) → C16H16Cl2O2S

Conditions	Yield
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) + 4-Vinylbenzyl chloride (1592-20-7) → decyldimethyl-(4-vinylbenzyl)ammonium chloride

Conditions	Yield
In acetonitrile at 40℃; for 239h;	99%

4-Vinylbenzyl chloride (1592-20-7) + potassium phtalimide (1074-82-4) → 2-(4-ethenylbenzyl)-1H-isoindole-1,3(2H)-dione (63413-74-1)

Conditions	Yield
In N,N-dimethyl-formamide	98%
In N,N-dimethyl-formamide at 110℃; for 5h;	88%
In N,N-dimethyl-formamide at 55℃; for 17h;	81%

styrene (292638-84-7) + 1,4-Divinylbenzene (105-06-6) + 4-Vinylbenzyl chloride (1592-20-7) → polymer; Monomer(s): styrene; 4-chloromethylstyrene; 1,4-divinylbenzene

Conditions	Yield
With dibenzoyl peroxide at 80℃; for 24h;	98%

4-Vinylbenzyl chloride (1592-20-7) → (4-vinyl-phenyl)-methanol (1074-61-9)

Conditions	Yield
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) + phenyltriisopropoxytitanium(IV) (16635-23-7) → phenyl(p-vinylphenyl)methane (15866-31-6)

Conditions	Yield
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 25℃; for 2h; Inert atmosphere;	98%

4-Vinylbenzyl chloride (1592-20-7) + undecyl 4'-hydroxybiphenyl-4-carboxylate (132328-89-3) → undecyl 4'-(4-vinylbenzyloxy)biphenyl-4-carboxylate (1104078-17-2)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 8h;	98%

4-Vinylbenzyl chloride (1592-20-7) + 2-hydroxyethanethiol (60-24-2) → 2-(4-vinyl-benzylsulfanyl)-ethanol (129509-07-5)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide In tetrahydrofuran; water Reflux;	98%

1H-imidazole (288-32-4) + 4-Vinylbenzyl chloride (1592-20-7) → 1-(4-vinylbenzyl)-1H-imidazole (78430-91-8)

Conditions	Yield
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) + propargyl alcohol (107-19-7) → 1-((prop-2-yn-1-yloxy)methyl)-4-vinylbenzene (132679-16-4)

Conditions	Yield
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%

Upstream product

• 1467-05-6 4-ethylbenzylchloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 53459-40-8 1-(2-chloroethyl)-4-(chloromethyl)benzene 
• 103-63-9 1-phenyl-2-bromoethane 
• 60-12-8 2-phenylethanol 
• 35793-35-2 p-chloromethyl-α-bromoethylbenzene 
• 100-41-4 ethylbenzene 
• 100-42-5 styrene 
• 107-30-2 chloromethyl methyl ether 
• 73291-09-5 4-chloromethylbenzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1074-61-9 (4-vinyl-phenyl)-methanol 
• 76297-21-7 1-(4-chloromethylphenyl)ethanol 
• 24249-98-7 p-chloromethyl-2-bromoethylbenzene 

Downstream Products

• 121383-67-3 1-(4-vinylbenzyl)cyclam 
• 151968-98-8 C₂₂H₂₆O₂ 
• 312767-10-5 3-(4-Vinylbenzyloxy)benzyl alcohol 
• 64268-25-3 4-(Trimethylsilylmethyl)styrene 
• 304014-53-7 3,5-bis(p-vinylphenylmethyloxy)benzyl alcohol 
• 216104-33-5 benzoic acid 2-(4-chloromethyl-phenyl)-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethyl ester 
• 92035-97-7 4-(4-ethenylbenzyloxy)butan-1-ol 
• 749253-21-2 1-(2,2,2-tris-trimethylsilanyl-ethyl)-4-vinyl-benzene 
• 868162-38-3 5-(4-ethenylphenyl)methoxymethyl-1,3-dithiane 
• 863986-81-6 N'-(2,6-dimethyl-phenyl)-N-pyridin-2-ylmethyl-N-(4-vinyl-benzyl)-ethane-1,2-diamine 
• 849146-76-5 3-ethyl-3-[[6-((4-vinylphenyl)methyl)oxyhexyl]oxymethyl]oxetane 

Relevant articles and documents

FACILE SYNTHESIS OF p-CHLOROMETHYLATED STYRENE BY ELIMINATION REACTION OF p-(2-BROMOETHYL)BENZYLCHLORIDE USING POTASSIUM HYDROXIDE AS A BASE UNDER PHASE TRANSFER CATALYSIS

Phase transfer catalyzed elimination reactions of p-(2-bromoethyl)-benzylchloride with potassium hydroxide gave p-chloromethylated styrene in high yield.

Preparation method of P-chloromethyl styrene

The invention relates to the field of organic chemistry, in particular to a preparation method of p-chloromethyl styrene. The invention provides a preparation method of p-chloromethyl styrene, which comprises the following step: carrying out elimination reaction on 1-(2-chloroethyl)-4-chloromethylbenzene under alkaline conditions to prepare the p-chloromethyl styrene. According to the preparation method, the reaction raw materials with relatively low price are utilized, the manufacturing cost is reduced, the manufacturing process is simple and safe, various side reactions are less, the product conversion rate is high, the purity is high, and thus a good industrialization prospect can be realized.

Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX

The direct selective halogenation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450-500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.

Aromatic cation activation: Nucleophilic substitution of alcohols and carboxylic acids

A new method for the nucleophilic substitution of alcohols and carboxylic acids using aromatic tropylium cation activation has been developed. This article reports the use of chloro tropylium chloride for the rapid generation of alkyl halides and acyl chlorides under very mild reaction conditions. It demonstrates, for the first time, the synthetic potential of tropylium cations in promoting chemical transformations.