2351-50-0

Basic information

• Product Name: 4-IODOSTYRENE)
• Synonyms: 4-IODOSTYRENE);Benzene, 1-ethenyl-4-iodo-;1-Ethenyl-4-iodobenzene, 1-Iodo-4-vinylbenzene;KWHSBYQFELZKKS-UHFFFAOYSA-N
• CAS NO: 2351-50-0
• Molecular Formula: C₈H₇I
• Molecular Weight: 230.043
• Mol File: 2351-50-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 44-44.5 °C
• Boiling Point: 235.6°C at 760 mmHg
• Flash Point: 102.3°C
• Appearance: /
• Density: 1.673g/cm³
• Vapor Pressure: 0.0762mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-IODOSTYRENE)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOSTYRENE)(2351-50-0)
• EPA Substance Registry System: 4-IODOSTYRENE)(2351-50-0)

Safety Data

• Hazardous Substances Data: 2351-50-0(Hazardous Substances Data)

Usage

General Description

4-Iodostyrene is a chemical compound with the molecular formula C8H7I. It is a derivative of styrene, containing an iodine atom at the 4-position of the phenyl ring. 4-Iodostyrene is primarily used as a building block in organic synthesis, particularly in the production of various polymers and pharmaceutical compounds. It is also employed as a reagent in cross-coupling reactions to form carbon-carbon bonds. Additionally, 4-Iodostyrene is utilized in the preparation of fluorescent dyes and as a starting material for the synthesis of various organic compounds. Due to its versatile application in chemical synthesis, 4-Iodostyrene is an important intermediate in the production of a wide range of industrial and research chemicals.

InChI:InChI=1/C8H7I/c1-2-7-3-5-8(9)6-4-7/h2-6H,1H2

Synthetic route

formaldehyd (50-00-0) + 4-iodo-benzyl alcohol (18282-51-4) → 4-iodostyrene (2351-50-0)

Conditions	Yield
Stage #1: 4-iodo-benzyl 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%

1-bromo-4-ethenyl-benzene (2039-82-9) → 4-iodostyrene (2351-50-0)

Conditions	Yield
Stage #1: 1-bromo-4-ethenyl-benzene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78 - 20℃;	94%
Stage #1: 1-bromo-4-ethenyl-benzene With sec.-butyllithium In tetrahydrofuran; cyclohexane for 3h; Inert atmosphere; Glovebox; Stage #2: With iodine In tetrahydrofuran; cyclohexane at -78℃; Inert atmosphere;	73%
Stage #1: 1-bromo-4-ethenyl-benzene With indium; bathophenanthroline; 3-chloroprop-1-ene; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	70 %Chromat.

Methyltriphenylphosphonium bromide (1779-49-3) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 110℃; for 10h; Inert atmosphere;	88%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-(iodophenyl)carboxaldehyde In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	76%

tri-n-butyl(vinyl)tin (7486-35-3) + (p-iodophenyl)(phenyl)iodonium bromide (59696-21-8) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide for 0.166667h; Ambient temperature;	85%

para-diiodobenzene (624-38-4) + vinyl magnesium bromide (1826-67-1) → 1,4-Divinylbenzene (105-06-6) + 4-iodostyrene (2351-50-0)

Conditions	Yield
Stage #1: vinyl magnesium bromide With indium(III) chloride In tetrahydrofuran Stage #2: para-diiodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Heating;	A 82% B 2%

tetravinylsilane (1112-55-6) + para-diiodobenzene (624-38-4) → 1,4-Divinylbenzene (105-06-6) + 4-iodostyrene (2351-50-0)

Conditions	Yield
With potassium fluoride; Pd (1.09 wt%)/TiO2 In N,N-dimethyl-formamide at 130℃; under 1500.15 Torr; for 1.5h; Hiyama Coupling; Inert atmosphere;	A 80% B 11%

4-Vinylphenylboronic acid (2156-04-9) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 81℃; for 25h;	78%
With N-iodo-succinimide In acetonitrile at 81℃; Darkness;	63%

methyl-triphenylphosphonium iodide (2065-66-9) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-iodostyrene (2351-50-0)

Conditions	Yield
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: p-(iodophenyl)carboxaldehyde In tetrahydrofuran at 20 - 55℃; for 5.5h; Inert atmosphere;	77%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene (870004-04-9) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; potassium iodide In methanol; water at 80℃; for 1h; High pressure;	66%

p-vinylbenzoyl chloride (1565-41-9) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h;	49%

4-iodobenzenediazonium tetrafluoroborate (1514-50-7) + ethenyltrimethylsilane (754-05-2) → 4-iodostyrene (2351-50-0) + [1-(4-Iodo-phenyl)-vinyl]-trimethyl-silane (94397-82-7) + (E)-4-iodostyryltrimethylsilane (94397-79-2)

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 25℃;	A 41 % Chromat. B 5 % Chromat. C 35%

4-iodobenzenesulfonyl chloride (98-61-3) + dimethylphenylvinylsilane (1125-26-4) → 4-iodostyrene (2351-50-0) + (E)-(4-iodostyryl)dimethyl(phenyl)silane

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); lithium carbonate In 1,4-dioxane at 100℃; for 24h; Heck Reaction; Schlenk technique; Inert atmosphere; stereoselective reaction;	A n/a B 31%

1-phenyl-2-bromoethane (103-63-9) → 4-iodostyrene (2351-50-0)

Conditions	Yield
(i) aq. HIO3, I2, H2SO4, AcOH, CCl4, (ii) KOH, EtOH; Multistep reaction;

N-nitrosoacetanilide (938-81-8) + C8H7IN2O2 (19260-02-7) → 4-iodostyrene (2351-50-0) + [1-(4-Iodo-phenyl)-vinyl]-trimethyl-silane (94397-82-7) + (E)-4-iodostyryltrimethylsilane (94397-79-2)

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 40℃; for 1.5h; Yield given. Yields of byproduct given;

para-diiodobenzene (624-38-4) + ethenyltrimethylsilane (754-05-2) → trimethylsilyl iodide (16029-98-4) + Hexamethyldisiloxane (107-46-0) + 4-iodostyrene (2351-50-0) + buta-1,3-diene (106-99-0)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II)) In tetralin; water; N,N-dimethyl-formamide at 100℃; for 5h; other catalysts: (Ph3P)4Pd, LiPdCl3, (PhCN)2PdCl2, (MeCN)2PdCl2, Pd/C; Et3N presence; Further byproducts given;	A n/a B n/a C 5 % Chromat. D n/a

4-iodobenzenediazonium tetrafluoroborate (1514-50-7) + ethenyltrimethylsilane (754-05-2) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With hydrogenchloride; bis(dibenzylideneacetone)-palladium(0) 1.) CH3CN, 25 deg C; Yield given. Multistep reaction;

tri-n-butyl(vinyl)tin (7486-35-3) + μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine] (88016-29-9) → para-diiodobenzene (624-38-4) + 4-iodostyrene (2351-50-0)

Conditions	Yield
With palladium dichloride In water; acetonitrile for 0.416667h; Ambient temperature; Yield given. Yields of byproduct given;

(+-)-4-iodo-1-<1-hydroxy-ethyl>-benzene → 4-iodostyrene (2351-50-0)

Conditions	Yield
With potassium hydrogensulfate; hydroquinone at 200 - 210℃; under 120 - 130 Torr;

formaldehyd (50-00-0) + Br(1-)*C13H21IP(1+) → 4-iodostyrene (2351-50-0)

Conditions	Yield
With potassium carbonate In water at 100℃; for 0.0833333h; Wittig reaction; Microwave irradiation;

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73852-88-7) → 4-iodostyrene (2351-50-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; dimethyl sulfoxide / 0.5 h / 0 - 25 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate; iodine / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere View Scheme

C14H19BIO2(1-)*ClMg(1+) → 4-iodostyrene (2351-50-0)

Conditions	Yield
Stage #1: C14H19BIO2(1-)*ClMg(1+) With iodine; sodium methylate In tetrahydrofuran; methanol at 0℃; for 0.5h; Inert atmosphere; Stage #2: Inert atmosphere;	23 mg

4-iodostyrene (2351-50-0) + 3-phenoxyphenylboronic acid (221006-66-2) + Trimethylacetic acid (75-98-9) → C21H16O2

Conditions	Yield
With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; iron(II) chloride In chloroform at 120℃; for 15h;	97%

4-iodostyrene (2351-50-0) + phenylmethanethiol (100-53-8) → benzyl(4-iodophenethyl)sulfane (1411817-07-6)

Conditions	Yield
With tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 2.5h; Sealed tube; Irradiation; regioselective reaction;	95%

4-iodostyrene (2351-50-0) → 1-(1-bromoethyl)-4-iodobenzene (68120-55-8)

Conditions	Yield
With silica gel; phosphorus tribromide In dichloromethane at 20℃; for 0.75h;	95%

carbon monoxide (201230-82-2) + 4-iodostyrene (2351-50-0) + diisobutyl[(1E)-oct-1-en-1-yl]aluminum (40098-43-9, 99591-51-2) → (E)-3-hexyl-1-(4-vinylphenyl)undec-4-en-1-one

Conditions	Yield
With palladium on activated charcoal; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran; hexane at 80℃; under 1500.15 Torr; for 16h; Autoclave; Inert atmosphere;	90%

4-iodostyrene (2351-50-0) + C9H7F5N2O2S → C10H9F2I

Conditions	Yield
With meso-tetraphenylporphyrin iron(III) chloride; potassium carbonate In 1,4-dioxane at 40℃; for 22h; Sealed tube; Inert atmosphere; diastereoselective reaction;	90%

carbon dioxide (124-38-9) + 4-iodostyrene (2351-50-0) → 4-ethenylbenzoic acid (1075-49-6)

Conditions	Yield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;	87%

bromodichloromethane (75-27-4) + 4-iodostyrene (2351-50-0) → C9H8Cl2IN3

Conditions	Yield
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	84%

Togni's reagent (887144-97-0) + pyridine-4-carbonitrile (100-48-1) + 4-iodostyrene (2351-50-0) → C14H11F3IN

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In tert-butyl methyl ether at 20℃; UV-irradiation;	83%

4-iodostyrene (2351-50-0) + isopropylamine (75-31-0) → 4-(4-iodophenyl)-2-methylbutan-2-amine

Conditions	Yield
With eosin In acetonitrile at 20℃; Irradiation; Green chemistry;	83%

N-formyldiethylamine (617-84-5) + trimethylsilyl cyanide (7677-24-9) + 4-iodostyrene (2351-50-0) → 1-ethyl-3-(4-iodophenyl)-5-methyl-1H-pyrrole-2-carbonitrile

Conditions	Yield
With iodine In neat (no solvent) for 0.666667h; Irradiation; Green chemistry; regioselective reaction;	81%

4-iodostyrene (2351-50-0) + acetylsulfanyl-4-(ethynyl)benzene (170159-24-7) → Thioacetic acid S-[4-(4-vinyl-phenylethynyl)-phenyl] ester

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃; for 20h;	80%

chloroform (67-66-3) + 4-iodostyrene (2351-50-0) + 3-phenoxyphenylboronic acid (221006-66-2) → C21H16O2

Conditions	Yield
With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; Trimethylacetic acid at 120℃; for 12h;	80%

carbon monoxide (201230-82-2) + 4-iodostyrene (2351-50-0) + phosphonic acid diethyl ester (762-04-9) → C13H17O4P

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at -78 - 40℃; under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique;	79%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-iodostyrene (2351-50-0) + trimethylaluminum (75-24-1) → 1-(4-vinylphenyl)propane-1,2-dione

Conditions	Yield
Stage #1: tert-butylisonitrile; 4-iodostyrene; trimethylaluminum With 1,3-bis-(diphenylphosphino)propane; palladium dichloride In toluene at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: With potassium tert-butylate In toluene at 20 - 100℃; for 16h; Sealed tube; Inert atmosphere; Stage #3: With hydrogenchloride; water In toluene at 20℃; for 1h; Sealed tube; Inert atmosphere;	75%

3-bromo-9H-carbazole (1592-95-6) + 4-iodostyrene (2351-50-0) → 3-bromo-9-(4-vinylphenyl)-9H-carbazole

Conditions	Yield
With dibenzo-18-crown-6; copper; potassium carbonate In toluene at 100℃; for 6h;	74.9%

4-iodostyrene (2351-50-0) + acetic anhydride (108-24-7) → 1-(4-iodophenyl)ethane-1,2-diyl diacetate

Conditions	Yield
With 2,2':6,2''-terpyridine; oxygen; palladium diacetate; acetic acid; bis(pinacol)diborane In acetonitrile at 90℃; under 760.051 Torr; for 30h; Sealed tube;	72%

4-iodostyrene (2351-50-0) + malononitrile (109-77-3) → 2-(4-vinyl-phenyl)-malononitrile (866416-42-4)

Conditions	Yield
Stage #1: malononitrile With sodium hydride In 1,2-dimethoxyethane at 20℃; for 1h; Stage #2: 4-iodostyrene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1,2-dimethoxyethane at 85℃; for 2h;	71.8%
Stage #1: malononitrile With sodium hydride In 1,2-dimethoxyethane at 20℃; for 1h; Stage #2: 4-iodostyrene; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 85℃; for 2h; Further stages.;	71.8%

4-iodostyrene (2351-50-0) + bis(pinacol)diborane (73183-34-3) → 2-(1-(4-iodophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
With palladium diacetate; acetic acid; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine In acetonitrile at 90℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	70%

pyridine-4-carbonitrile (100-48-1) + 4-iodostyrene (2351-50-0) + sodium methansulfinate (20277-69-4) → C14H14INO2S

Conditions	Yield
With 9,10-diphenylanthracene; ammonium chloride In ethanol; acetonitrile at 20℃; for 4h; Irradiation;	69%

4-iodostyrene (2351-50-0) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;	69%

4-iodostyrene (2351-50-0) + benzene (71-43-2) → (E)-1-(4-iodophenyl)-2-phenylethene (13041-71-9)

Conditions	Yield
With di-μ-acetatotetrakis(dihaptoethene)dirhodium(I); copper(II) dipivaloate; Trimethylacetic acid at 165℃; for 24h; Sealed tube;	68%

4-iodostyrene (2351-50-0) + silver(I) trifluoromethanethiolate (811-68-7) → 1-(4-iodophenyl)-2-((trifluoromethyl)thio)ethanone

Conditions	Yield
With dipotassium peroxodisulfate; oxygen In dimethyl sulfoxide at 35℃; for 3h; Schlenk technique;	68%

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 938-81-8 N-nitrosoacetanilide 
• 19260-02-7 C₈H₇IN₂O₂ 
• 50-00-0 formaldehyd 
• 18282-51-4 4-iodo-benzyl alcohol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 766-99-4 1-ethynyl-4-iodobenzene 
• 918540-55-3 4-(4-iodophenyl)-2-butanone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 98-61-3 p-Iodobenzenesulfonyl chloride 
• 1125-26-4 dimethylphenylvinylsilane 
• 1112-55-6 tetravinylsilane 

Downstream Products

• 223556-23-8 4-(4-ethenylphenyl)-morpholine 
• 866416-42-4 2-(4-vinyl-phenyl)-malononitrile 
• 1076-96-6 methyl 4-vinylbenzoate 
• 78812-64-3 2-hydroxy-1-(4-iodophenyl)ethan-1-one 
• 109086-21-7 (+/-)-2-(4-iodophenyl)oxirane 
• 96388-70-4 4-vinylphenylcyanamide 

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