1073-67-2

Basic information

• Product Name: 4-Chlorostyrene
• Synonyms: P-CHLOROSTYRENE;1-chloro-4-ethenyl-benzen;1-chloro-4-ethenylbenzene;1-Chloro-4-vinylbenzene;4-chloro-styren;Benzene, 4-chloro-1-ethenyl-;benzene,1-chloro-4-ethenyl-;Parachlorostyrene
• CAS NO: 1073-67-2
• Molecular Formula: C₈H₇Cl
• Molecular Weight: 138.59
• EINECS: 214-028-8
• Product Categories: Styrenes;Monomers;Polymer Science;Styrene and Functionalized Styrene Monomers
• Mol File: 1073-67-2.mol
• Article Data: 166

Chemical Properties

• Melting Point: -16 °C
• Boiling Point: 192 °C(lit.)
• Flash Point: 140 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.155 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.68 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.565(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Immiscible with water.
• BRN: 1098859
• CAS DataBase Reference: 4-Chlorostyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorostyrene(1073-67-2)
• EPA Substance Registry System: 4-Chlorostyrene(1073-67-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26-36
• RIDADR: 1993
• WGK Germany: 3
• RTECS: CZ0533000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1073-67-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
4-Chlorostyrene is used as a research compound for studying chemical and biochemical properties of the vinyl group of styrene by developing structure-activity relationships (SAR).
Used in Catalyst Preparation:
In the field of catalysis, 4-Chlorostyrene is used as a precursor in the preparation of new bis(pyrazolyl)borato olefin complexes of copper(I), which are important for various catalytic applications.
Used in Polymer Chemistry:
4-Chlorostyrene is used as a monomer in the graft copolymerization with acrylonitrile (AN) onto ethylene-propylene-diene terpolymer (EPDM) in the presence of benzoyl peroxide (initiator), contributing to the development of new polymer materials.
Used in Organic Synthesis:
4-Chlorostyrene plays an important role in the preparation of 4-[(4-chloro-phenyl)-thioacetyl]-morpholine, a compound that may have potential applications in various chemical and pharmaceutical processes.
Used in Reaction Mechanism Studies:
4-Chlorostyrene is also employed in the investigation of regioselectivity in the cationic Heck reaction of 4-substituted styrenes, providing insights into reaction mechanisms and improving synthetic methodologies.

Preparation

Synthesis of 4-chlorostyrene: carry out catalytic dehydration reaction by 4-chlorophenethylalcohol at 280°C, the used catalyst is a modified aluminum silicate catalyst, and the yield is 80%.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 852, 1947 DOI: 10.1021/ja01196a033Tetrahedron Letters, 31, p. 5061, 1990 DOI: 10.1016/S0040-4039(00)97806-7

InChI:InChI=1/C8H7Cl/c1-2-7-3-5-8(9)6-4-7/h2-6H,1H2

Synthetic route

p-chlorocinnamic acid (1615-02-7) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt; sodium hydroxide at 160℃; for 5h;	99%
With copper In quinoline
With ferulic acid decarboxylase from Saccharomyces cerevisiae In aq. phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.4; Kinetics; Enzymatic reaction;

formaldehyd (50-00-0) + para-Chlorobenzyl alcohol (873-76-7) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
Stage #1: para-Chlorobenzyl alcohol With triethylphosphine hydrobromide at 100℃; for 0.166667h; Microwave irradiation; Stage #2: formaldehyd With potassium carbonate In water at 100℃; for 0.0833333h; Microwave irradiation;	97%

4-n-chlorophenylacetylene (873-73-4) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With hydrogen In toluene at 20℃; under 22801.5 Torr; for 12h; Autoclave; chemoselective reaction;	96%
With piperazine; NiO doped titania In methanol at 20℃; for 3h; Inert atmosphere; Sealed tube; UV-irradiation;	95%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; ethanol; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 70℃; for 22h; Inert atmosphere; stereoselective reaction;	91%

1,2-dibromo-1-(4-chlorophenyl)ethane (23135-16-2) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With indium; cobalt(II) chloride hexahydrate In methanol at 20℃; for 1h;	95%
With gallium; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Ultrasonic irradiation; chemoselective reaction;	95%
With indium; niobium pentachloride In tetrahydrofuran at 20℃; for 0.166667h; Sonication; chemoselective reaction;	95%

2-(4-chlorophenyl)thiirane → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With molybdenum hexacarbonyl In toluene for 1h; Reflux; chemoselective reaction;	95%

1-Chloro-4-iodobenzene (637-87-6) + vinyltrimethyltin (754-06-3) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 20℃; for 0.166667h;	94%

1-chloro-4-(2,2-dibromovinyl)benzene (77295-59-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With samarium In methanol at 45℃; for 6h;	94%

1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole (61078-14-6) + 4-chlorobenzaldehyde (104-88-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	93%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	93%

4-Chlorostyrene oxide (2788-86-5) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With sodium iodide; tin(ll) chloride In ethanol for 0.0666667h; Reflux; Green chemistry;	92%
With carbon monoxide In tetrahydrofuran; water at 110℃; under 6840.46 Torr; for 2h; Autoclave; chemoselective reaction;	85%
With iododioxobis(triphenylphosphine)rhenium(V) In toluene for 0.583333h; Reflux; chemoselective reaction;	78%

1-allyl-4-chlorobenzene (1745-18-2) + ethene (74-85-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; di-μ-bromobis-(tritert-butylphosphine)dipalladium(I) In tetrahydrofuran at 60℃; under 7500.75 Torr; for 16h; Autoclave;	92%

4-chlorobenzaldehyde (104-88-1) + diazomethyl-trimethyl-silane (18107-18-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With Rh(I)[PPh2CH2CH2Si(OEt)3]3Cl; triphenylphosphine; isopropyl alcohol In tetrahydrofuran at 25℃; for 4h; Reagent/catalyst; chemoselective reaction;	87%

1-Chloro-4-iodobenzene (637-87-6) + Triethoxyvinylsilane (78-08-0) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With sodium hydroxide In methanol; water at 100℃; for 10h; Hiyama Coupling; Sealed tube;	86%

(iodomethyl)triphenylphosphonium iodide (3020-28-8) + 4-chlorobenzaldehyde (104-88-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With dibutyl telluride In tetrahydrofuran at 80℃; for 22h;	85%

(vinyl)trimethoxylsilane (2768-02-7) + 1-Chloro-4-iodobenzene (637-87-6) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With sodium hydroxide; palladium diacetate In water at 120℃; for 0.166667h; Hiyama reaction; microwave irradiation;	84%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-chlorobenzaldehyde (104-88-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 5h; Wittig reaction; Heating;	82%
Stage #1: Methyltriphenylphosphonium bromide With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.5h; Reflux; Stage #2: 4-chlorobenzaldehyde In dichloromethane for 5h; Reflux;	82%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran for 0.25h; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran Wittig olefination; Further stages.;	73%

1-Chloro-4-iodobenzene (637-87-6) + ethene (74-85-1) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With 10H-phenothiazine; bis(μ-chloro)bis{(2-(1-(hydroxyimino)methyl)phenyl-C1,N)palladium(II)}; potassium acetate In N,N-dimethyl acetamide at 105℃; under 775.743 Torr; Heck-Mizoroki reaction; Inert atmosphere;	82%
With sodium acetate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 90℃; under 7600.51 Torr; Heck reaction; Inert atmosphere; Autoclave;
With N-Methyldicyclohexylamine; palladium diacetate; tetra-(n-butyl)ammonium iodide; tri tert-butylphosphoniumtetrafluoroborate In methanol; toluene at 130℃; under 7500.75 Torr; for 0.333333h; Heck Reaction;

bromochlorobenzene (106-39-8) + potassium vinyltrifluoroborate → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; for 4h; Suzuki-Miyaura reaction;	81%

tricyclohexyl(hydroxymethyl)phosphonium tetrafluoroborate + 4-chlorobenzyl bromide (622-95-7) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; Wittig Olefination;	81%

[2-(4-Chloro-phenyl)-ethyl]-trimethyl-stannane (104586-14-3) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With tris(4-methylphenyl)methylium tetrafluoroborate In 1,2-dichloro-ethane at 20℃;	79%

1-Chloro-4-iodobenzene (637-87-6) + ethenyltrimethylsilane (754-05-2) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With potassium fluoride; 4 A molecular sieve; tetrabutyl-ammonium chloride; bis(dibenzylideneacetone)-palladium(0) In toluene for 24h; Ambient temperature;	79%

Methyl phenyl sulfone (3112-85-4) + para-Chlorobenzyl alcohol (873-76-7) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With sodium hydride In mineral oil at 135℃; for 10h; Inert atmosphere; Schlenk technique;	79%

bromochlorobenzene (106-39-8) + Vinyl bromide (593-60-2) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With palladium diacetate; C22H27P; triethylamine In 1,4-dioxane; Hexadecane at 120℃; under 15001.5 Torr; for 20h; Heck Reaction; Schlenk technique; Inert atmosphere;	79%

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
at 140℃; for 4h; Ionic liquid;	70%
With copper In quinoline at 185 - 195℃; Decarboxylation;	50%
With quinoline; copper
With hydrogen bromide; acetic acid at 100℃; Erwaermen des Reaktionsprodukts mit wss. Na2CO3-Loesung auf dem Dampfbad;

Trifluoro-methanesulfonate1-[2-(4-chloro-phenyl)-ethyl]-4,6-diphenyl-[2,2']bipyridinyl-1-ium; → 4-vinylbenzyl chloride (1073-67-2) + 4,6-Diphenyl-[2,2']bipyridinyl; compound with trifluoro-methanesulfonic acid

Conditions	Yield
at 260℃; under 1 Torr;	A 70% B n/a

1-Chloro-4-(chloromethyl)benzene (104-83-6) + tricyclohexyl(hydroxymethyl)phosphonium tetrafluoroborate → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; Wittig Olefination;	69%

bromochlorobenzene (106-39-8) + cobalt chloride (II) (CoCl2) + chloroethylene (75-01-4) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With ammonium chloride In tetrahydrofuran; nitrogen	67.1%
With ammonium chloride In tetrahydrofuran; nitrogen	67.1%
With ammonium chloride In dibutyl ether; nitrogen	55.4%

(E)-[2-(4-chlorophenyl)ethenyl]trimethylsilane (88691-45-6, 132536-25-5, 88691-39-8) + propionic acid anhydride (123-62-6) → 4-vinylbenzyl chloride (1073-67-2) + (E)-1-(4-chlorophenyl)pent-1-en-3-one

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 120℃; for 24h; Inert atmosphere;	A n/a B 67%

1-(4-chlorophenyl)prop-2-yn-1-ol (29805-11-6) + benzoic acid (65-85-0) → 4-vinylbenzyl chloride (1073-67-2) + 1-(4-chlorophenyl)-2-oxopropyl benzoate (1241573-14-7)

Conditions	Yield
With RuCl2(η-C6H6)(TPPMS) In water at 100℃; for 6h; Inert atmosphere;	A 6% B 65%

bromochlorobenzene (106-39-8) + rhodium chloride trihydrate (III) (RhCl3.3H2O) + chloroethylene (75-01-4) → 4-vinylbenzyl chloride (1073-67-2)

Conditions	Yield
With ammonium chloride In tetrahydrofuran; nitrogen	64.8%

4-vinylbenzyl chloride (1073-67-2) → 1,2-dibromo-1-(4-chlorophenyl)ethane (23135-16-2)

Conditions	Yield
With bromine In chloroform at 0℃; Inert atmosphere;	100%
With Oxone; ammonium bromide In water; acetonitrile for 13h; Reflux;	96%
With acetic acid; lithium bromide at 25℃; for 2h; Green chemistry;	95%

4-vinylbenzyl chloride (1073-67-2) → 2-bromo-1-(4-chlorophenyl)ethanol (6314-52-9)

Conditions	Yield
With N-Bromosuccinimide; water In acetonitrile at 20℃;	100%
With trifluoroacetic acid; potassium bromide In water; dimethyl sulfoxide at 50℃; for 1.6h; Reagent/catalyst; Electrolysis;	94%
With (2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid; water; N-bromoacetamide In tert-butyl alcohol at 20℃; for 0.5h; regioselective reaction;	84%

4-vinylbenzyl chloride (1073-67-2) → 4-Chlorostyrene oxide (2788-86-5)

Conditions	Yield
With 1,1,1-trifluoro-2-propanone; dihydrogen peroxide	100%
With tert.-butylhydroperoxide; 2C13H10N3O2(1-)*MoO2(2+) In methanol; dichloromethane for 1h; Catalytic behavior; Reagent/catalyst;	100%
With tert.-butylhydroperoxide; cis-[MoO2(N'-(3-ethoxy-2-hydroxybenzylidene)-2-methoxybenzohydrazide-2H)(OH2)] In methanol; dichloromethane for 1h; Catalytic behavior; Reflux;	100%

4-vinylbenzyl chloride (1073-67-2) + 5-(4-methoxyphenyl)-2-phenyl-2H-tetrazole (20433-10-7) → 5-(4-chlorophenyl)-3-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (75745-49-2)

Conditions	Yield
In benzene for 2h; UV-irradiation;	100%

4-vinylbenzyl chloride (1073-67-2) + 4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidine → (E)-(4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidyl)(4-chlorophenyl)ethene

Conditions	Yield
bis(ethylene)rhodium(I) chloride dimer In toluene byproducts: 4-chlorophenylethane; under Ar; to a soln. of the Rh-complex in toluene was added the arylethene, reaction with the oxaazaborolidine for 4 h; distn.; elem. anal.;	100%

4-vinylbenzyl chloride (1073-67-2) + (2,2-difluoroethyl)diphenylsulfonium trifluoromethanesulfonate → 1-chloro-4-(trans-2-(difluoromethyl)cyclopropyl)benzene

Conditions	Yield
With meso-tetraphenylporphyrin iron(III) chloride; cesium fluoride; zinc In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere; diastereoselective reaction;	100%

1-oxothiolane (1600-44-8) + 4-vinylbenzyl chloride (1073-67-2) + trifluoromethylsulfonic anhydride (358-23-6) → (E)-1-(4-chlorostyryl)tetrahydro-1H-thiophen-1-ium trifluoromethanesulfonate

Conditions	Yield
In dichloromethane at -40 - 20℃; Inert atmosphere;	100%

4-vinylbenzyl chloride (1073-67-2) → 4-chloro(ethylbenzene) (622-98-0)

Conditions	Yield
With hydrogen In ethanol at 60℃; under 3000.3 Torr; for 5h;	99%
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	99%
With triethylsilane; 1% Pd on activated carbon In water at 20℃; for 2h; Reagent/catalyst; Green chemistry; chemoselective reaction;	99%

4-vinylbenzyl chloride (1073-67-2) + [N-(p-tolylsulfonyl)imino]phenyliodinane (55962-05-5) → N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine (97401-93-9)

Conditions	Yield
With [CuI(tris[(tetramethylguanidino)-phenyl]amine)][PF6] In acetonitrile for 2h; Inert atmosphere; Molecular sieve;	99%
With copper-loaded dopamine-grafted Fe3O4 nanoparticles In acetonitrile at 70℃; for 2h; Inert atmosphere; Microwave irradiation; Green chemistry;	96%
With [PhB{CH2P(p-CF3Ph)2}3]Cu(PPh3) In dichloromethane at 20℃; for 5h; Inert atmosphere; Schlenk technique;	95%

4-vinylbenzyl chloride (1073-67-2) + dimethyl diazomalonate (6773-29-1) → dimethyl 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate (127604-92-6, 132145-65-4)

Conditions	Yield
Stage #1: 4-vinylbenzyl chloride With bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)] In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: dimethyl diazomalonate In dichloromethane at 0 - 23℃; Inert atmosphere;	99%
Stage #1: 4-vinylbenzyl chloride; dimethyl diazomalonate In dichloromethane at 0 - 22℃; Inert atmosphere; Stage #2: With tetrakis(hydroxymethyl)phosphonium hydroxide In benzene at 60℃; for 12h;	99%
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In dichloromethane at 20℃; for 2h; Inert atmosphere;	90%

4-vinylbenzyl chloride (1073-67-2) → 1-(p-chlorophenyl)-1,2-ethanediol (7477-64-7)

Conditions	Yield
With water; 3-chloro-benzenecarboperoxoic acid at 30℃; for 2h;	99%
With dihydrogen peroxide; ethyl acetate; lipase [PSLG6] In water at 60℃; for 0.0833333h; microwave irradiation;	90%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 0 - 20℃; for 18h; Inert atmosphere;	90%

4-vinylbenzyl chloride (1073-67-2) → 4-chlorobenzaldehyde (104-88-1)

Conditions	Yield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;	99%
With sodium periodate; C22H23ClIN2Os(1+)*F6P(1-) In water; tert-butyl alcohol at 60℃; for 1h; Schlenk technique; Inert atmosphere;	99%
With sodium periodate; C18H15ClFN2Ru(1+)*Cl(1-) In water; tert-butyl alcohol at 60℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere;	99%

4-vinylbenzyl chloride (1073-67-2) + 4-bromo-benzaldehyde (1122-91-4) → (E)-4-(4-chlorostyryl)benzaldehyde (52792-18-4)

Conditions	Yield
With sodium acetate In N,N-dimethyl-formamide for 3h; Heck Reaction; Schlenk technique; Inert atmosphere; Reflux;	99%
With C28H34ClN3O5Pd; sodium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 20h; Heck Reaction;	95%
With sodium acetate; tetraphenylphosphonium bromide; palladium dichloride In N,N-dimethyl-formamide at 140℃; for 1.5h; Arylation; Heck reaction;	99 % Chromat.
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 140℃; Heck Reaction;

4-vinylbenzyl chloride (1073-67-2) → 1-chloro-4-(1-iodoethyl)benzene

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; iodine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl at 20℃; under 30003 Torr; for 6h;	99%
With polymethylhydrosiloxane; iodine In chloroform at 20℃; for 0.333333h;	95%
With phosphoric acid; iodine Inert atmosphere; Schlenk technique; Green chemistry;	84%
With triethylsilane; tetrafluoroboric acid; iodine; copper(II) oxide In dichloromethane at -30℃; for 3h;	61%

4-vinylbenzyl chloride (1073-67-2) + 4-cyanobenzaldehyde (105-07-7) → 4-[3-chloro-3-(4-chloro-phenyl)-1-hydroxy-propyl]-benzonitrile

Conditions	Yield
Stage #1: 4-vinylbenzyl chloride; 4-cyanobenzaldehyde With phenylborondichloride In dichloromethane at 25℃; for 12h; Stage #2: With water	99%

4-vinylbenzyl chloride (1073-67-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2-(4-chlorophenyl)ethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 20℃; for 24h;	99%
With bis(diphenylphosphino)butane; bis(1,5-cyclooctadiene)diiridium(I) dichloride In tetrahydrofuran under N2; pinacol borane was reacted with ligand in THF at room temp. for 24 h in the presence of Ir-complex and bis(diphenylphosphino)butane; chromy.;	99%
With sodium triethylborohydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; toluene at 100℃; for 24h; Microwave irradiation; Inert atmosphere; regioselective reaction;	96%

4-vinylbenzyl chloride (1073-67-2) + t-butyl diazoacetate (35059-50-8) → tert-butyl (1R*,2S*)-2-(4-chlorophenyl)cyclopropane-1-carboxylate

Conditions	Yield
With C67H51IrN2O2 In tetrahydrofuran at -78℃; for 24.1667h; optical yield given as %ee; enantioselective reaction;	99%
chiral phenyliridium(III)-salen complex In tetrahydrofuran at -78 - 20℃;	99 % Spectr.

4-vinylbenzyl chloride (1073-67-2) + iodobenzene (591-50-4) → 1-chloro-4-styrylbenzene (1657-49-4, 1657-50-7, 4714-23-2, 130059-92-6, 130059-96-0)

Conditions	Yield
With tetrabutyl ammonium fluoride; palladium diacetate; potassium carbonate at 70℃; for 36h; Heck reaction; air;	99%
With triethylamine In water; acetonitrile at 60℃; for 2h; Heck Reaction;	98%
With potassium hydroxide In water; N,N-dimethyl-formamide at 90℃; for 2h;	96%

4-vinylbenzyl chloride (1073-67-2) + para-iodoanisole (696-62-8) → 4-chloro-4'-methoxy-stilbene (5043-91-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; triethylamine In N,N-dimethyl-formamide at 200℃; for 0.166667h; Heck reaction; Microwave irradiation;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; triethylamine In N,N-dimethyl-formamide at 200℃; for 0.166667h; Mizoroki-Heck reaction; Microwave irradiation;	99%
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 120℃; for 4h; Heck Reaction;	99%

4-vinylbenzyl chloride (1073-67-2) + 1-Bromo-4-fluorobenzene (460-00-4) → ClSBF (39769-26-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; tetrabutylammomium bromide; sodium acetate In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Heck reaction; Microwave irradiation;	99%
With 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; tetrabutylammomium bromide; sodium acetate; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Mizoroki-Heck reaction; Microwave irradiation;	99%
With potassium phosphate; C34H46Br4N8Pd2 In N,N-dimethyl-formamide at 110℃; for 4h; Heck Reaction;	80%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 1-[phenyl(piperidin-1-yl)methyl]naphthalen-2-ol In N,N-dimethyl acetamide at 140℃; for 40h; Heck Reaction; Inert atmosphere;

diazoacetic acid ethyl ester (623-73-4) + 4-vinylbenzyl chloride (1073-67-2) → ethyl (1R,2S)-2-(4-chlorophenyl)cyclopropane-1-carboxylate (395683-39-3)

Conditions	Yield
With C20H21ClN3ORh; silver trifluoromethanesulfonate In dichloromethane at 0℃; Inert atmosphere; diastereoselective reaction;	99%

3-diazo-3,6-dihydro-2H-pyran-2-one (919299-02-8) + 4-vinylbenzyl chloride (1073-67-2) → C13H11ClO2 (1161824-01-6)

Conditions	Yield
Stage #1: 3-diazo-3,6-dihydro-2H-pyran-2-one; 4-vinylbenzyl chloride In dichloromethane at -78℃; for 0.166667h; Molecular sieve; Inert atmosphere; Stage #2: With C67H51IrN2O2 In dichloromethane at -78℃; for 72h; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

4-vinylbenzyl chloride (1073-67-2) + phenylboronic acid (98-80-6) → (E)-1-(4-chlorophenyl)-2-phenylethene (1657-50-7)

Conditions	Yield
With C38H36Cl2Fe2N2Pd2; oxygen In N,N-dimethyl-formamide at 50℃; for 3h; Heck reaction;	99%
With palladium diacetate; acetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid at 90℃; for 27h; Heck reaction;	99%
With [2,2]bipyridinyl; methanesulfonic acid; palladium(II) trifluoroacetate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique;	95%

4-vinylbenzyl chloride (1073-67-2) + 1,1-Diphenylmethanol (91-01-0) → (E)-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl)dibenzene (1104997-38-7)

Conditions	Yield
With trifluorormethanesulfonic acid In ethylene dibromide at 60℃; Air atmosphere; stereoselective reaction;	99%
With N-octadecyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In dichloromethane at 80℃; for 12h;	89%
With iron(III) chloride hexahydrate; toluene-4-sulfonic acid In dichloromethane at 45℃; for 24h; stereospecific reaction;	80%

4-vinylbenzyl chloride (1073-67-2) + di(p-tolyl) disulfide (103-19-5) → (1-(4-chlorophenyl)ethane-1,2-diyl)bis(p-tolylsulfane) (1313220-39-1)

Conditions	Yield
With iodine In water at 20℃; for 12h;	99%

4-vinylbenzyl chloride (1073-67-2) + [bis(acetoxy)iodo]benzene (3240-34-4) → 1-chloro-4-styrylbenzene (1657-49-4, 1657-50-7, 4714-23-2, 130059-92-6, 130059-96-0)

Conditions	Yield
With palladium diacetate; potassium carbonate In PEG-400 at 60℃; for 18h; Heck type coupling reaction; under air;	99%

4-vinylbenzyl chloride (1073-67-2) + 3-methyl-1,3-diphenylcyclobutanol → 3-methyl-1,3-diphenyl-4-(4-vinylphenyl)butan-1-one (1359763-70-4)

Conditions	Yield
With 1,4-bis(dicyclohexylphosphino)butane di-trifluoroborate; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere;	99%

4-vinylbenzyl chloride (1073-67-2) + para-chloroacetophenone (99-91-2) → 1-{4-[(E)-2-(4-chlorophenyl)ethenyl]phenyl}ethanone (63483-67-0)

Conditions	Yield
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 2h; Heck Reaction;	99%
With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 2h; Heck Reaction; Inert atmosphere; Schlenk technique;	90%
With tetrabutylammomium bromide; palladium diacetate; silica gel; potassium carbonate for 1h; Neat (no solvent);	77%
With [PdBr2(PPh3)2]; potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24h; Heck Reaction; Inert atmosphere; stereoselective reaction;	38%

4-vinylbenzyl chloride (1073-67-2) + 1-(N,N‑dimethylcarbamoyl)indole (70957-05-0) → (E)-2-(4-chlorostyryl)-N,N-dimethyl-1H-indole-1-carboxamide (1454704-55-2)

Conditions	Yield
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper(II) acetate monohydrate In tetrahydrofuran at 100℃; for 24h; Heck Reaction; Inert atmosphere; stereoselective reaction;	99%
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	72%
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; oxygen; copper diacetate; sodium acetate In 1,2-dichloro-ethane at 20 - 100℃; under 760.051 Torr; for 15.25h; Sealed tube; Inert atmosphere;	65%

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 17277-94-0 (4-chloro-phenethyl)-dimethyl sulfonium ; bromide 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 108-24-7 acetic anhydride 
• 104-88-1 4-chlorobenzaldehyde 
• 917-64-6 methyl magnesium iodide 
• 6068-86-6 (2-(p-Chlorophenyl)ethyl)trimethylammonium bromide 
• 106-39-8 bromochlorobenzene 
• 74-85-1 ethene 
• 1615-02-7 p-chlorocinnamic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 754-06-3 vinyltrimethyltin 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 42945-85-7 2-(4-chlorophenyl)-1-(morpholin-4-yl)-ethanethione 
• 511533-74-7 1-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene 
• 23135-16-2 1,2-dibromo-1-(4-chlorophenyl)ethane 
• 1009-43-4 4-(trimethylsilyl)styrene 
• 99-91-2 para-chloroacetophenone 
• 70263-54-6 [5-(4-chloro-phenyl)-2-phenyl-isoxazolidin-3-yl]-phenyl-methanone 
• 1824-55-1 6-chloro-3-(4-chloro-benzyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide 
• 42866-89-7 2-(4-chlorophenyl)acetaldehyde dimethyl acetal 
• 91647-69-7 Diaethoxy-<4-vinyl-phenyl>-phosphin 
• 57765-59-0 2-(p-Chlorophenyl)isopropylidenecyclopropane 
• 132949-21-4 acetic acid 2-acetoxy-1-(4-chloro-phenyl)-ethyl ester 
• 37470-97-6 7-(4-chloro-phenyl)-5-phenyl-1,5,6,7-tetrahydro-pyrano[2,3-d]pyrimidine-2,4-dione 
• 70372-46-2 (+/-)-1-(4-chlorophenyl)-2-thiocyanatoethyl acetate 
• 67917-42-4 6-(4-chloro-phenyl)-2-phenyl-5,6-dihydro-4H-[1,3]thiazine 

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