636-98-6

Basic information

• Product Name: 1-Iodo-4-nitrobenzene
• Synonyms: Benzene,1-iodo-4-nitro-;p-Nitrophenyl iodide;4-Iodonitrobenzene,>97%;4-Iodonitrobenzene, 98+%;1-Iodo-4-nitrobenzene,98+%;4-IODONITROBENZENE / 1-IODO-4-NITROBENZENE;4-NITRO-1-IODOBENZENE;1-Iodo-4-nitrobenzene,99%
• CAS NO: 636-98-6
• Molecular Formula: C₆H₄INO₂
• Molecular Weight: 249.01
• EINECS: 202-676-4
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Benzene derivates;API intermediates;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;alkyl Iodine|nitro-compound
• Mol File: 636-98-6.mol
• Article Data: 102

Chemical Properties

• Melting Point: 171-173 °C(lit.)
• Boiling Point: 289 °C772 mm Hg(lit.)
• Flash Point: 100 °C
• Appearance: Brownish/Powder
• Density: 1.8090
• Vapor Pressure: 0.00417mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep Cold
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1100378
• CAS DataBase Reference: 1-Iodo-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Iodo-4-nitrobenzene(636-98-6)
• EPA Substance Registry System: 1-Iodo-4-nitrobenzene(636-98-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-36-33
• Safety Statements: 26-37/39-36/37/39-36
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT, KEEP COLD, LIGHT SENSI
• Hazardous Substances Data: 636-98-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

1-Iodo-4-nitrobenzene is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Purification Methods

Precipitate it from acetone by addition of water, followed by recrystallisation from EtOH. [Beilstein 8 H 523, 8 H 523, 8 II 191, 8 III 623, 8 IV 743.]

InChI:InChI=1/C6H4INO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H

Synthetic route

4-nitro-aniline (100-01-6) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With potassium iodide; 10-camphorsulfonic acid; sodium nitrite In acetic acid at 20℃; for 24h; Time;	100%
With Nitrogen dioxide; sodium iodide In acetonitrile at -20℃; for 10h;	98%
Stage #1: 4-nitro-aniline With toluene-4-sulfonic acid In water at 20℃; Stage #2: With potassium iodide In water at 20℃; for 1.5h;	95%

p-nitrobenzene diazonium nitrate → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With potassium iodide for 24h;	100%

4-nitrobenzenediazonium tetrafluoroborate (456-27-9) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With iodine; dibenzyl hantzsch ester In dimethyl sulfoxide at 20℃;	99%
With trimethylsilyl iodide; methyl iodide In N,N-dimethyl-formamide for 1h; Ambient temperature;	91%
With iodine; potassium iodide In dimethyl sulfoxide at 15℃;

1-(4-nitrophenyl)-2-(pyrrolidin-1-yl)diazene (52010-82-9) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With iodine In various solvent(s) at 100℃; for 12h;	98%
With trifluoroacetic acid; potassium iodide In water Yield given;

(4-nitrophenyl)(phenyl)iodonium tetrafluoroborate → p-nitrobenzene iodide (636-98-6) + para-dinitrobenzene (100-25-4) + iodobenzene (591-50-4) + nitrobenzene (98-95-3)

Conditions	Yield
With sodium nitrite In chloroform; water at 56℃; for 1h;	A 1% B 98% C 93 % Chromat. D 1 % Chromat.

4-nitrobenzenediazonium 4-methylbenzenesulfonate (1947-33-7) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With potassium iodide In water at 20℃; for 0.0833333h;	98%
With potassium iodide In water for 0.333333h; paste form;

4-nitrobenzenediazonium trifluoromethanesulfonate → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With potassium iodide In water at 20℃;	98%

iodobenzene (591-50-4) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + benzoyl chloride (98-88-4)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 95%

para-iodoanisole (696-62-8) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Kinetics; Solvent; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;	A n/a B 95%

para-diiodobenzene (624-38-4) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-iodobenzoic acid chloride (1711-02-0)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 95%

4-tolyl iodide (624-31-7) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-methyl-benzoyl chloride (874-60-2)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 94%

4-iodobenzoic acid ethyl ester (51934-41-9) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + ethyl 4-(chlorocarbonyl)benzoate (27111-45-1)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 94%

1-Chloro-4-iodobenzene (637-87-6) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-chloro-benzoyl chloride (122-01-0)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 93%

1,4-bromoiodobenzene (589-87-7) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-chlorobenzoyl chloride (586-75-4)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 93%

3-Iodotoluene (625-95-6) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 3-Methylbenzoyl chloride (1711-06-4)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 93%

4-nitrobenzenediazonium o-benzenedisulfonimide → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 0.75h; Substitution;	92%

4-nitro-benzoyl chloride (122-04-3) + 5-iodo-1,3-benzodioxole (5876-51-7) → p-nitrobenzene iodide (636-98-6) + 3,4-(methylenedioxy)benzoyl chloride (25054-53-9)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 92%

4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6)

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;	91%
With 2,2'-azobis(isobutyronitrile); 2-mercaptopyridine-1-oxide sodium salt; methyl iodide In toluene for 0.583333h; Heating; Yield given;

4-fluoro-1-iodobenzene (352-34-1) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-fluorobenzoyl chloride (403-43-0)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 91%

3,5-dimethylphenyl iodide (22445-41-6) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 3,5-dimethylbenzoyl chloride (6613-44-1)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 91%

1-Fluoro-3-iodobenzene (1121-86-4) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 3-fluorobenzoyl chloride (1711-07-5)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 91%

4-iodophenylboronic acid (5122-99-6) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Inert atmosphere; Schlenk technique;	91%

4-nitro-benzoyl chloride (122-04-3) + 2-(4-iodophenyl)-2-methyl-[1,2]-dioxolane (214701-35-6) → p-nitrobenzene iodide (636-98-6) + C11H11ClO3

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 90%

tert-butyl 2-(4-nitrophenyl)diazenecarboxylate (92722-14-0) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With iodine; trifluoroacetic acid In acetonitrile at 80℃; for 0.5h;	89%
With iodine; trifluoroacetic acid In acetonitrile at 80℃;	89%
With iodine; trifluoroacetic acid In acetonitrile at 80℃; for 4h;	80%

3,3-dimethyl-1-(4-nitrophenyl)triazene (7227-92-1) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With hydrogen iodide In acetonitrile at 60℃; for 0.25h;	88%

bis(trifluoromethanesulfonyl)amide (82113-65-3) + 4-nitro-aniline (100-01-6) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
Stage #1: bis(trifluoromethanesulfonyl)amide With tert.-butylnitrite; acetic acid In ethanol Cooling with ice; Stage #2: 4-nitro-aniline With tetraethylammonium iodide In water at 20℃;	88%

para-nitrophenyl bromide (586-78-7) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With tributylphosphine; sodium iodide; nickel dibromide In 1-methyl-pyrrolidin-2-one at 180℃; for 3h; Finkelstein reaction; Inert atmosphere; Molecular sieve; Sealed tube;	87%
With copper(I) oxide; L-proline; potassium iodide In ethanol at 110℃; for 30h; Schlenk technique; Inert atmosphere; Sealed tube;	85%
With KI-CuI-alumina In various solvent(s) at 150℃; for 6h;	78 % Chromat.
With copper(l) iodide; 3-azapentane-1,5-diamine; sodium iodide In acetonitrile at 110℃; for 24h; Finkelstein Reaction; Inert atmosphere;	60 %Chromat.

4-nitrophenylboronic acid (24067-17-2) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24h;	87%
With sodium nitrite In acetonitrile at 80℃; for 8h; Sealed tube;	87%

4-nitro-benzoyl chloride (122-04-3) + 5-iodo-1-(4-methylphenylsulfonyl)indole (174715-24-3) → p-nitrobenzene iodide (636-98-6) + C16H12ClNO3S

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 85%

4-iodobenzonitrile (3058-39-7) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-cyanobenzoyl chlorIde (6068-72-0)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;	A n/a B 82%

p-nitrobenzene iodide (636-98-6) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With hydrazine hydrate In methanol at 26℃; for 0.166667h; Reagent/catalyst; Solvent;	100%
With cadmium sulphide; ammonium formate In water at 20℃; for 20h; Inert atmosphere; Irradiation; Sealed tube;	100%
With magnesium; nickel dichloride In water at 20℃; for 12h; Sealed tube; Photolysis; Inert atmosphere;	100%

pyrrolidine (123-75-1) + p-nitrobenzene iodide (636-98-6) → 1-(4-nitro-phenyl)-pyrrolidine (10220-22-1)

Conditions	Yield
In tetrahydrofuran at 50℃; under 9000720 Torr; for 20h;	100%
With copper(l) iodide; 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 24h; Ullmann condensation; Inert atmosphere;	95%
With copper(l) iodide In N,N-dimethyl acetamide at 130℃; for 24h;	95%

piperidine (110-89-4) + p-nitrobenzene iodide (636-98-6) → 1-(4-nitrophenyl)piperidine (6574-15-8)

Conditions	Yield
In tetrahydrofuran at 50℃; under 9000720 Torr; for 20h;	100%
With potassium carbonate In dimethyl sulfoxide at 50℃;	100%
With sodium acetate In N,N-dimethyl-formamide for 8h;	95%

morpholine (110-91-8) + p-nitrobenzene iodide (636-98-6) → 1-morpholino-4-nitrobenzene (10389-51-2)

Conditions	Yield
In tetrahydrofuran at 50℃; under 9000720 Torr; for 50h;	100%
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 0.166667h;	98%
With sodium t-butanolate In dimethyl sulfoxide at 110℃; for 12h; Buchwald-Hartwig Coupling;	96%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + p-nitrobenzene iodide (636-98-6) → 1-(4-Nitro-phenyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; iodide (112473-28-6)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 75h;	100%
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; Yield given;

p-nitrobenzene iodide (636-98-6) + 1-Heptyne (628-71-7) → 1-(hept-1-ynyl)-4-nitrobenzene (64146-60-7)

Conditions	Yield
With copper(l) iodide; iodophenylbis(triphenylphosphine)palladium; triethylamine In chloroform at 60℃; for 1h;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tributyl-amine; potassium carbonate In water at 20℃; for 4h;	95%
With piperidine; 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene; tetrabutylammomium bromide; palladium diacetate In water; N,N-dimethyl-formamide at 40℃; for 3h; Sonogashira Cross-Coupling;	94%

p-nitrobenzene iodide (636-98-6) + carbon monoxide (201230-82-2) → 4-nitro-benzoic acid (62-23-7)

Conditions	Yield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 50℃; under 760 Torr; for 3h;	100%
With amphiphilic resin-supported phosphine-palladium; water; potassium carbonate at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;	100%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 50℃; for 3h; Product distribution; effect of different catalysts;	100%

p-nitrobenzene iodide (636-98-6) + trimethyl(phenyl)stannane (934-56-5) → 1-phenyl-4-nitrobenzene (92-93-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With Palladium nanoparticle cored dendrimer In tetrahydrofuran for 4h; Stille coupling; Reflux;	96%
With (4-nitrophenyl)Pd(P(C6H5)3)2I In N,N,N,N,N,N-hexamethylphosphoric triamide at 70℃; for 3.5h; Product distribution; other solvents; also in DMF in vacuum, in the air, and in O2 at various reaction times;	94 % Chromat.

p-nitrobenzene iodide (636-98-6) + carbon monoxide (201230-82-2) + triethylmethoxystannane (1067-21-6) → 4-nitrobenzoic acid methyl ester (619-50-1)

Conditions	Yield
With iodophenylbis(triphenylphosphine)palladium under 760 Torr; for 1h;	100%

p-nitrobenzene iodide (636-98-6) → bis(4-nitrophenyl)sulfide (1223-31-0)

Conditions	Yield
With bis(triethyltin) sulfide; iodophenylbis(triphenylphosphine)palladium In dimethyl sulfoxide for 4h; Heating;	100%
With potassium thioacyanate; cetyltrimethylammonim bromide; potassium hydroxide In water at 135℃; for 7h; Green chemistry;	100%
With copper(l) iodide; sodiumsulfide nonahydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere;	98%

p-nitrobenzene iodide (636-98-6) → nitrobenzene (98-95-3)

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide; RhCl(PPh3)3 In acetonitrile at 70℃; for 3h; Product distribution; other organic halides; var. times, var. temp., also in the presence of PNAH as reductant and Pd(OAc)2 as catalyst;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 6h; Inert atmosphere;	100%
With 18-crown-6 ether In diethyl ether; N,N-dimethyl-formamide for 4h; Heating;	84%

p-nitrobenzene iodide (636-98-6) + 2-(trimethylstannyl)thiophene (37496-13-2) → 2-(4-nitrophenyl)thiophene (59156-21-7)

Conditions	Yield
With lithium chloropalladite In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.5h; other reagents;	100%

p-nitrobenzene iodide (636-98-6) + phenylacetylene (536-74-3) → 4-(phenylethynyl)nitrobenzene (1942-30-9)

Conditions	Yield
With copper(l) iodide; triethylamine; titanium(IV) oxide at 20℃; for 24h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; palladium diacetate In acetonitrile at 20℃; for 6h; Sonogashira cross-coupling reaction;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; air; palladium diacetate In acetonitrile at 20℃; for 18h; Sonogashira reaction;	100%

p-nitrobenzene iodide (636-98-6) + acrylic acid methyl ester (292638-85-8) → p-nitrocinnamic acid methyl ester (637-57-0)

Conditions	Yield
With triethylamine; fluorine-substituted palladium In N,N-dimethyl-formamide at 140℃; for 3h; Heck reaction;	100%
With [P5(η3-allyl)(4,4'-(CF3(CF2)9CH2OCH2)-2,2'-bpy)][OTf]; triethylamine In N,N-dimethyl-formamide at 145℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Heck Reaction; Microwave irradiation;	100%
With palladium diacetate; triethylamine In toluene at 110℃; for 2.5h; Heck reaction;	99%

styrene (292638-84-7) + p-nitrobenzene iodide (636-98-6) → trans-4-nitrostilbene (1694-20-8)

Conditions	Yield
With [PdCl2(2-ethyl-2-oxazoline)2]; sodium acetate In N,N-dimethyl-formamide at 140 - 150℃; for 24h; Heck reaction;	100%
With tetrabutyl ammonium fluoride; palladium dichloride at 40℃; for 12h; Heck reaction; Inert atmosphere; neat (no solvent);	100%
With tributyl-amine In N,N-dimethyl-formamide at 120℃; for 24h; Heck-Mizoroki reaction; stereoselective reaction;	99%

p-nitrobenzene iodide (636-98-6) + phenylboronic acid (98-80-6) → 1-phenyl-4-nitrobenzene (92-93-3)

Conditions	Yield
With palladium diacetate; 4-Ph2P-C6H4-2-N-glucosamine; sodium carbonate In water at 60℃; for 1h; Product distribution; Further Variations:; Temperatures; Reagents; Suzuki cross-coupling reaction;	100%
With polyhydroxylated phosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 60℃; for 1h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In acetone at 110℃; for 2h; Suzuki-Miyaura cross-coupling reaction;	100%

p-nitrobenzene iodide (636-98-6) + 1-(thiophen-2-yl)prop-2-yn-1-ol (153026-78-9) → (E)-3-(4-nitropheny)-1-thiophen-3-yl-propenone (275815-89-9)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran Isomerization; Sonogashira coupling; Heating;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran for 9h; Sonogashira coupling-isomerization reaction; Heating;	95%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 16h; Sonogashira coupling; Isomerization; Heating;

p-nitrobenzene iodide (636-98-6) + tributylphenylstannane (960-16-7) → 1-phenyl-4-nitrobenzene (92-93-3)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 100℃; for 8h; Stille reaction;	100%
With palladium diacetate; orotic acid; cesium fluoride In 1,4-dioxane at 100℃; for 18h; Concentration; Time; Stille Cross Coupling; Sealed tube; Inert atmosphere; Schlenk technique;	100%
With C31H33INPPd In N,N-dimethyl-formamide at 80℃; for 24h; Stille coupling;	99%

indole (120-72-9) + p-nitrobenzene iodide (636-98-6) → 1-(4-nitrophenyl)-1H-indole (25688-27-1)

Conditions	Yield
With copper phthalocyanine; sodium hydroxide In dimethyl sulfoxide at 100℃;	100%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane; dodecane at 110℃; for 24h;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; caesium carbonate In 1,3,5-trimethyl-benzene at 180℃; for 24h; Inert atmosphere;	99%

p-nitrobenzene iodide (636-98-6) + acrylic acid n-butyl ester (141-32-2) → (E)-n-butyl 4-nitrocinnamate (86622-84-6, 131061-15-9)

Conditions	Yield
With C29H33Cl2N5Pd; tetrabutylammomium bromide; sodium carbonate In N,N-dimethyl acetamide at 140℃; for 3h; Heck reaction; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Heck reaction; Inert atmosphere; regioselective reaction;	99%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; diamminedichloropalladium(II); tributyl-amine In water at 140℃; for 12h; Mizoroki-Heck cross-coupling; Sealed tube;	99%

p-nitrobenzene iodide (636-98-6) + dichloromethylphenylsilane (149-74-6) → 1-phenyl-4-nitrobenzene (92-93-3)

Conditions	Yield
With potassium hydroxide; palladium on activated charcoal In water Heating;	100%

1H-imidazole (288-32-4) + p-nitrobenzene iodide (636-98-6) → 1-(4-nitrophenyl)-1H-imidazole (2301-25-9)

Conditions	Yield
With copper phthalocyanine; sodium hydroxide In dimethyl sulfoxide at 100℃;	100%
With Hippuric Acid; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 30h; Ullmann coupling reaction;	99%
With caesium carbonate In dimethyl sulfoxide at 110℃; for 1h; Ullmann Condensation;	98%

p-nitrobenzene iodide (636-98-6) + 4-methoxyphenylboronic acid (5720-07-0) → 4-methoxy-4'-nitrobiphenyl (2143-90-0)

Conditions	Yield
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;	100%
With palladium diacetate; 4-Ph2P-C6H4-2-N-glucosamine; sodium carbonate In tetrahydrofuran; ethanol; water at 60℃; for 18h;	99%
With polyhydroxylated phosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 60℃; for 18h;	99%

(Z)-3-methyl-4-phenyl-4-trimethylsilanylbut-3-en-2-ol (849213-47-4) + p-nitrobenzene iodide (636-98-6) → [1,2-dimethyl-3-(4-nitrophenyl)-3-phenylallyloxy]trimethylsilane

Conditions	Yield
With copper(l) iodide; lithium tert-butoxide; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 0.666667h;	100%

p-nitrobenzene iodide (636-98-6) + 1-decyne (764-93-2) → 1-(dec-1-ynyl)-4-nitrobenzene

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; palladium diacetate In acetonitrile at 20℃; for 6h; Sonogashira cross-coupling reaction;	100%
With caesium carbonate; 2-aminopyrimidine-4,6-diol; palladium diacetate In acetonitrile at 20℃; for 5h; Sonogashira reaction;	95%
With tetrabutyl ammonium fluoride; copper diacetate at 130 - 135℃; for 14h; Sonogashira cross-coupling reaction;	95%
With 1,4-diaza-bicyclo[2.2.2]octane; air; palladium diacetate In acetonitrile at 20℃; for 20h; Sonogashira reaction;	90%
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 135 - 140℃; for 4h; Sonogashira cross-coupling;

p-nitrobenzene iodide (636-98-6) + tert-Butyl acrylate (1663-39-4) → (E)-tert-butyl 3-(4-nitrophenyl)prop-2-enoate (370839-59-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 4h; Heck cross-coupling reaction;	100%
With tetrabutyl ammonium fluoride; palladium dichloride at 40℃; for 3h; Heck reaction; Inert atmosphere; neat (no solvent);	100%
With 1,4-diaza-bicyclo[2.2.2]octane; poly(ethylene glycol)-400; potassium carbonate; palladium diacetate In water at 80℃; for 4h; Heck cross-coupling;	98%

p-nitrobenzene iodide (636-98-6) + tributylstannylethynylbenzene (3757-88-8) → 4-(phenylethynyl)nitrobenzene (1942-30-9)

Conditions	Yield
With potassium fluoride; 1,4-dicyclohexyl-diazabutadiene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Stille cross-coupling reaction;	100%
diphenylphosphine-based palladium(0) complex on MCM-41 In water; N,N-dimethyl-formamide at 60℃; for 6h; Stille coupling;	87%
Stage #1: p-nitrobenzene iodide With diphenylphosphinoethane functionalized polystyrene resin-supported Pd(0) complex In N,N-dimethyl-formamide at 20℃; for 0.25h; Stille Cross Coupling; Stage #2: tributylstannylethynylbenzene In N,N-dimethyl-formamide at 65℃; for 7h; Stille Cross Coupling;	86%

p-nitrobenzene iodide (636-98-6) + 2-(tributylstannyl)furan (118486-94-5) → 2-(4-nitrophenyl)furan (28123-72-0)

Conditions	Yield
With potassium fluoride; 1,4-dicyclohexyl-diazabutadiene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Stille cross-coupling reaction;	100%

Upstream product

• 93680-33-2 C₈H₉N₇ 
• 75-30-9 2-iodo-propane 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 106-51-4 p-benzoquinone 
• 62-23-7 4-nitro-benzoic acid 
• 17026-17-4 3-hydroxy-3-phenyl-1-p-nitrophenyl-1-triazene 
• 74-88-4 methyl iodide 
• 7446-70-0 aluminium trichloride 
• 591-50-4 iodobenzene 
• 10544-72-6 dinitrogen tetraoxide 
• 7697-37-2 nitric acid 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 624-38-4 para-diiodobenzene 
• 13125-93-4 1-iodo-4-nitrosobenzene 

Downstream Products

• 90309-44-7 (2,5-dichloro-phenyl)-(4-nitro-phenyl)-sulfide 
• 42583-60-8 2,4-dichlorophenyl 4′-nitrophenyl sulfide 
• 86749-02-2 3,4-dichlorophenyl 4′-nitrophenyl sulfide 
• 603121-28-4 p,p'-diiodoazoxybenzene 
• 1223-31-0 bis(4-nitrophenyl)sulfide 
• 100-25-4 para-dinitrobenzene 
• 305-85-1 2,6-diiodo-4-nitrophenol 
• 709-49-9 1-iodo-2,4-dinitrobenzene 
• 1516-60-5 4-nitrophenyl azide 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 827-98-5 dichloro(4-nitrophenyl)-λ³-iodane 
• 14454-14-9 N-(4-iodophenyl)hydroxylamine 
• 1601-97-4 bis-(4-iodo-phenyl)-diazene 

Relevant articles and documents

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

Low-temperature and highly efficient liquid-phase catalytic nitration of chlorobenzene with NO2: Remarkably improving the para-selectivity in O2-Ac2O-Hβ composite system

In this work, we developed a low-temperature and efficient approach for the highly selective preparation of valuable p-nitrochlorobenzene from the liquid-phase catalytic nitration of chlorobenzene with NO2 in O2-Ac2O-Hβ composite system. The results demonstrated that the introduction of molecular oxygen remarkably enhanced the chlorobenzene conversion and the cooperation catalysis of Hβ zeolite and Ac2O envidently improved the selectivity to para-nitro product. Under the optimized reaction conditions, 93.6 % of the selectivity to p-nitrochlorobenzene with 84.0 % of chlorobenzene conversion was obtained, and the ratio of p-nitrochlorobenzene to o-nitrochlorobenzene could reach up to 20.3. Furthermore, the selectivity distribution of nitration products was reasonably explained by the density functional theory (DFT) calculation. Finally, the possible nitration reaction pathway of chlorobenzene with NO2 was suggested in O2-Ac2O-Hβ composite catalytic system. The present work affords a new and mild nitration approach for highly selective preparation of valuable para-nitro products, and has potential industrial application prospects.