540-37-4

Basic information

• Product Name: 4-Iodoaniline
• Synonyms: BENZENAMINE, 4-IODO-;1-amino-4-iodobenzene;4-IODOANILINE;P-IODOANILINE;4-iodo-anilin;4-iodo-benzenamin;4-iodobenzenamine;4-iodo-Benzenamine
• CAS NO: 540-37-4
• Molecular Formula: C₆H₆IN
• Molecular Weight: 219.02
• EINECS: 208-743-4
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;API intermediates;Anilines, Amides & Amines;Iodine Compounds;C2 to C6;Nitrogen Compounds;Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pharmaceutical Intermediates
• Mol File: 540-37-4.mol
• Article Data: 257

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 268.7 °C at 760 mmHg
• Flash Point: 116.3 °C
• Appearance: Beige to grayish-brown/Crystalline Powder or Needles
• Density: 1.8155 (estimate)
• Vapor Pressure: 0.00758mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Store below +30°C.
• Solubility: H2O: slightly soluble
• PKA: 3.81(at 25℃)
• Water Solubility: Slightly soluble in water.Soluble in chloroform, methanol.
• Sensitive: Light Sensitive
• Merck: 14,5027
• BRN: 774101
• CAS DataBase Reference: 4-Iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodoaniline(540-37-4)
• EPA Substance Registry System: 4-Iodoaniline(540-37-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36
• RIDADR: 2811
• WGK Germany: 3
• RTECS: BY3850000
• F: 8
• TSCA: T
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 540-37-4(Hazardous Substances Data)

Usage

Chemical Properties

beige to greyish-brown crystalline powder. soluble in alcohol, ether and chloroform, slightly soluble in water.

Uses

Different sources of media describe the Uses of 540-37-4 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Iodoaniline is a iodine substituted aniline that is widely used as chemical intermediates in the manufacturing of pesticides, dyes and drugs. 4-Iodoaniline was shown to be a more potent nephrotoxica nt in vitro than other anilines.
3. 4-dehydroanilinium ion, a stable distonic isomer of ionized aniline, by collision-activated dissociation of protonated 4-iodoaniline. Palladium-catalyzed carbonylation of 4-iodoaniline gave the corresponding four- armed star polybenzamides. 4-Iodoaniline is a iodine substituted aniline that is widely used as chemical intermediates in the manufacturing of dyes and drugs. 4-Iodoaniline was used to prepare phenyl functionalized graphene oxide (I-Ph-GO).

Preparation

4-Iodoaniline is obtained by the reaction of aniline and iodine in the presence of sodium bicarbonate. Add aniline and sodium bicarbonate to water and slowly add crushed iodine in stages with vigorous stirring. If the reaction solution is yellow, add a little sodium bisulfite to make it discolor, then filter and get the crude product. Then the product is recrystallized by ethanol to obtain 4-Iodoaniline.

General Description

4-Iodoaniline is the most potent methaemoglobin former.

Purification Methods

Crystallise it from pet ether (b 60-80o) by refluxing, then cool it in an ice-salt bath freezing mixture. Dry it in air. Alternatively, crystallise it from EtOH and dry it in vacuo for 6hours at 40o [Edidin et al. J Am Chem Soc 109 3945 1987]. The N-acetyl derivative has m 184o (from MeOH). [Beilstein 12 IV 1544.]

InChI:InChI=1/C6H6IN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

Synthetic route

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%

4-aminobenzenediazonium 4-methylbenzenesulfonate (1059625-65-8) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With potassium iodide In water at 20℃; for 0.833333h;	100%

aniline (62-53-3) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With tetramethylammonium dibromoiodate(I) at 20℃; for 0.0833333h;	99%
With iodine at 30℃; for 12h; Reagent/catalyst; Solvent; Green chemistry; regioselective reaction;	97%
With sulfuric acid; dihydrogen peroxide; potassium iodide In methanol at 20℃; for 4h;	96%

1,4-phenylenediamine (106-50-3) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
Stage #1: 1,4-phenylenediamine With toluene-4-sulfonic acid In water at 20℃; Stage #2: With potassium iodide In water at 20℃; for 1.5h;	98%

1-azido-4-iodo-benzene (53694-87-4) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;	96%
With methanol; samarium; iodine for 6h; Ambient temperature;	91%
Stage #1: 1-azido-4-iodo-benzene With hydrazine hydrate for 0.166667h; Inert atmosphere; Stage #2: for 12h; Irradiation; chemoselective reaction;	90%

bis-(4-iodo-phenyl)-diazene (1601-97-4, 21650-53-3) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With polystyrene-CH2-NH3(+)HCO2(-); magnesium In methanol at 20℃; for 0.2h;	96%
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 0.2h;	95%
With aminomethylpolystyrene-supported formate; palladium on activated charcoal In methanol at 20℃; for 2.5h;	95%
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.75h; pH=2; Inert atmosphere; Irradiation;	86%

2-oxo-2-phenylethyl (4-iodophenyl)carbamate → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2.5h; Sealed tube; Irradiation; Inert atmosphere;	93%

2,2,2-trichloroethyl (4-iodophenyl)carbamate → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane at 60℃; Inert atmosphere; chemoselective reaction;	93%

4-bromo-aniline (106-40-1) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With copper(I) oxide; L-proline; potassium iodide In ethanol at 110℃; for 30h; Schlenk technique; Inert atmosphere; Sealed tube;	90%

1-(4-iodophenyl)ethanol (68120-56-9, 104013-25-4, 53207-29-7) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube;	90%
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 4h; Reagent/catalyst;	90%

aniline (62-53-3) → 2-iodophenylamine (615-43-0) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With potassium ferrate(VI); iodine In hexane for 1.5h; Reflux; regioselective reaction;	A n/a B 88%
With hydrogenchloride; potassium iodate; potassium iodide In methanol; water at 20℃;	A n/a B 65%
With N-iodo-succinimide; perchloric acid In acetic acid at 35℃; Kinetics; Mechanism; Thermodynamic data; other temperatures; dependence on the concentrations of substrate; E(activ.), ΔH(excit.), ΔS(excit.);

N-Boc-4-iodoaniline (159217-89-7) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With methanol; oxalyl dichloride at 20℃; for 2h;	86%

2-(4-iodophenoxy)propanamide (1247414-30-7) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry;	85%
With potassium hydroxide at 140℃;	177.3 mg

p-nitrobenzene iodide (636-98-6) → 1-iodo-4-nitrosobenzene (13125-93-4) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
Stage #1: p-nitrobenzene iodide With ammonium chloride; zinc In 2-methoxy-ethanol at 20℃; for 0.5h; Reduction; Stage #2: With iron(III) chloride In ethanol; water at 0℃; for 3h; Oxidation;	A 82% B n/a

p-nitrobenzene iodide (636-98-6) → aniline (62-53-3) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With Rh/Al2O3; hydrogen In water; toluene at 80℃; under 30003 Torr; for 24h; Reagent/catalyst; Pressure; Temperature;	A 22% B 78%
With Rh/Al2O3; hydrogen In water; toluene at 60℃; under 30003 Torr; for 24h; Reagent/catalyst; Pressure; Temperature;	A 60% B 38%
With water; iron at 210℃; for 2h;	A 37 % Chromat. B 52 % Chromat.

indole (120-72-9) + p-nitrobenzene iodide (636-98-6) + 2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) → 1-(1H-indol-3-yl)-2-phenyl-1, 2, 3, 4-tetrahydroisoquinoline + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With Co(dmgH)2Cl2; Eosin Y In water; acetonitrile at 20℃; for 48h; Inert atmosphere; Irradiation; Sealed tube;	A 78% B 85 %Spectr.

4-iodophenylboronic acid (5122-99-6) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;	74%
With O-(2,4-dinitrophenyl)hydroxylamine In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;	60%
With copper(I) oxide; ammonium hydroxide In water for 0.0833333h; Microwave irradiation;

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

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

p-iodo-N-methylaniline (60577-34-6) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With piperidine; dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at -78℃; for 40h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;	65%

4-iodocumene (17356-09-1) → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 4h; Sealed tube;	61%
With sodium azide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 4h;	61%

C15H12I2N2 (51218-04-3) → β-(p-Jodanilino)acrolein (51218-00-9) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With water; sodium acetate; acetic acid In ethanol; acetone; benzene at 70℃; for 49.5h;	A 36% B 55%

aniline (62-53-3) → 2,4-diiodoaniline (533-70-0) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With ammonium peroxydisulfate; potassium iodide In methanol; water at 20℃;	A 8% B 55%
With 1-(2-hydroxy-4-methoxyphenyl)ethanone; iodine In benzene for 36h; Irradiation;
With 1-(2-hydroxy-4-methoxyphenyl)ethanone; iodine In benzene for 36h; Irradiation;
With N-iodo-succinimide; zirconium(IV) chloride In dichloromethane at 0℃; for 2h; Conversion of starting material;
With 1-butyl-3-methyl-pyridinium dichloroiodate for 2h;	A 19 %Chromat. B 80 %Chromat.

p-nitrobenzene iodide (636-98-6) → p,p'-diaminobiphenyl (92-87-5) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	A 27% B 55%

4-chloro-aniline (106-47-8) → aniline (62-53-3) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
With triethylamine; sodium iodide In acetonitrile for 2h; Irradiation;	A 5% B 51%

potassium (4-iodophenyl)trifluoroborate → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile for 3h; Sonication;	49%

iodobenzene (591-50-4) + trifluorormethanesulfonic acid (1493-13-6) → 2-iodophenylamine (615-43-0) + (4-iodophenyl)(phenyl)iodonium trifluoromethanesulfonate (144930-55-2) + p-aminoiodobenzene (540-37-4)

Conditions	Yield
Stage #1: trifluorormethanesulfonic acid With xenon difluoride; trimethylsilyl isocyanate In dichloromethane at -78℃; Stage #2: iodobenzene In dichloromethane at -78℃;	A n/a B 44% C n/a

C21H26IN2O4Pol → p-aminoiodobenzene (540-37-4)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; BAL lantane; Product distribution / selectivity;	38%

1-azido-4-iodo-benzene (53694-87-4) + diethylamine (109-89-7) → Diethyl-(5-iodo-3H-azepin-2-yl)-amine + p-aminoiodobenzene (540-37-4)

Conditions	Yield
In cyclohexane Ambient temperature; Irradiation; Title compound not separated from byproducts;	A 34% B 12%

1-hexene (592-41-6) + 4-chloro-aniline (106-47-8) → aniline (62-53-3) + p-aminoiodobenzene (540-37-4) + 4-(2-iodohexyl)aniline + 4-(1-(iodomethyl)pentyl)aniline

Conditions	Yield
With sodium iodide In acetonitrile ionic Meerwein arylation; Irradiation;	A 3% B 12% C 32% D 10%

benzaldehyde (100-52-7) + p-aminoiodobenzene (540-37-4) → N-benzylidene-4-iodoaniline (3381-47-3, 102904-39-2)

Conditions	Yield
In ethanol for 1h; Sonication;	100%
In benzene Heating;	83%
In ethanol Heating;	57%

p-toluenesulfonyl chloride (98-59-9) + p-aminoiodobenzene (540-37-4) → N-tosyl-4-iodoaniline (158268-30-5)

Conditions	Yield
With triethylamine In dichloromethane at 4℃;	100%
With triethylamine In dichloromethane at 0 - 20℃;	96%
With pyridine at 85℃; for 4h;	87%

benzaldehyde (100-52-7) + acetophenone (98-86-2) + p-aminoiodobenzene (540-37-4) → [3-(phenyl)-3-((4-iodophenyl)amino)-1-phenylpropan-1-one] (94871-48-4)

Conditions	Yield
sodium tetrakis(3,5-trifluoromethylphenyl)borate In water at 30℃; for 24h; Mannich reaction;	100%
With nitrogen and sulfur doped porous carbon catalyst In ethanol at 20℃; for 6.5h;	91%
With hydrogenchloride In ethanol at 10℃; for 10h;	90%

Acetic formic anhydride (2258-42-6) + p-aminoiodobenzene (540-37-4) → N-(4-iodo-phenyl)-formamide (6393-17-5)

Conditions	Yield
In tetrahydrofuran at -20℃; for 0.25h;	100%
In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere;	97%
In tetrahydrofuran at 0 - 20℃;

(2-formylphenyl)butyl tellurium dibromide (128346-30-5) + p-aminoiodobenzene (540-37-4) → 2-(4'-iodophenyliminomethinyl)phenyltellurenyl bromide (130191-26-3)

Conditions	Yield
With trifluoroacetic acid In benzene	100%

bis(trichloromethyl) carbonate (32315-10-9) + p-aminoiodobenzene (540-37-4) → 1-iodo-4-isocyanatobenzene (15845-62-2)

Conditions	Yield
With triethylamine In dichloromethane	100%
In ethyl acetate for 4h; Heating;	74%
With triethylamine In dichloromethane at -35 - 20℃; for 2h;	60%

di-tert-butyl dicarbonate (24424-99-5) + p-aminoiodobenzene (540-37-4) → N-Boc-4-iodoaniline (159217-89-7)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃;	100%
In neat (no solvent) at 80℃; for 0.166667h; Temperature; Green chemistry; chemoselective reaction;	98%
Stage #1: p-aminoiodobenzene With triethylamine In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 6h;	97.5%

4-methoxyphenylboronic acid (5720-07-0) + p-aminoiodobenzene (540-37-4) → 4-(4-methoxyphenyl)aniline (1137-77-5)

Conditions	Yield
With sodium carbonate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;	100%
With potassium carbonate In ethanol at 78℃; for 1h; Suzuki-Miyaura coupling; Air atmosphere;	96%
With potassium carbonate In methanol; water at 40 - 45℃; for 1.5h; Suzuki Coupling;	92%

formaldehyd (50-00-0) + p-aminoiodobenzene (540-37-4) → 4-Iodo-N,N-dimethylaniline (698-70-4)

Conditions	Yield
With sodium cyanoborohydride In acetic acid	100%
With sodium cyanoborohydride In acetic acid at 20℃; for 12h;	96%
With sodium cyanoborohydride; acetic acid at 22℃; Inert atmosphere; Schlenk technique;	91%

2,5-hexanedione (110-13-4) + p-aminoiodobenzene (540-37-4) → 1-(2,5-dimethyl-1H-pyrrol-1-yl)-4-iodobenzene (288608-09-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Inert atmosphere; Schlenk technique;	100%
With nano-Fe3O4 immoblized lewis acidic ionic liquid In neat (no solvent) at 20℃; for 0.5h; Paal-Knorr Pyrrole Synthesis; Sonication;	98%
With toluene-4-sulfonic acid In toluene for 4h; Inert atmosphere; Reflux;	97%

3-chloro-3-oxopropanoic acid methyl ester (37517-81-0) + p-aminoiodobenzene (540-37-4) → methyl 3-((4-iodophenyl)amino)-3-oxopropanoate (658709-61-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In ethyl acetate at 20℃; for 16h; Cooling with acetone-dry ice;	99%
With triethylamine In ethyl acetate at 10 - 15℃; for 0.5h;	29.8 g

6,7-dimethoxy-4-chloroquinazoline (13790-39-1) + p-aminoiodobenzene (540-37-4) → 11N-070 (168835-91-4)

Conditions	Yield
With isopropyl alcohol Heating;	100%
In isopropyl alcohol for 3h; Heating / reflux;	95%

p-aminoiodobenzene (540-37-4) + 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline (183322-18-1) → [6,7-bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(4-iodo-phenyl)-amine (882511-65-1)

Conditions	Yield
With isopropyl alcohol Heating;	100%

(cyclopent-2-eneyl)acetic acid (13668-61-6) + p-aminoiodobenzene (540-37-4) → 2-cyclopent-2-enyl-N-(4-iodo-phenyl)-acetamide

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	100%

BOC-glycine (4530-20-5) + p-aminoiodobenzene (540-37-4) → [(4-iodophenylcarbamoyl)methyl]carbamic acid tert-butyl ester (216774-64-0)

Conditions	Yield
With dacarbazine; dmap In dichloromethane	100%
With dmap; diisopropyl-carbodiimide In dichloromethane for 20h; Inert atmosphere;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h;	98%

1-ethynyl-3-trifluoromethylbenzene (705-28-2) + p-aminoiodobenzene (540-37-4) → C15H10F3N (869578-08-5)

Conditions	Yield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In diethylamine at 50℃;	100%

4-chloro-benzoyl chloride (122-01-0) + p-aminoiodobenzene (540-37-4) → 4-chloro-N-(4-iodo-phenyl)-benzamide (299954-64-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 4h;	100%
With triethylamine In tetrahydrofuran at 20℃; for 4h;	100%

glyoxylic acid ethyl ester (924-44-7) + p-aminoiodobenzene (540-37-4) → ethyl 2-((4-iodophenyl)imino)acetate

Conditions	Yield
With magnesium sulfate In toluene at 25℃; for 0.5h;	100%
With sodium sulfate In benzene at 20℃;
With sodium sulfate In toluene at 20℃; for 0.5h; Inert atmosphere;

p-aminoiodobenzene (540-37-4) + Acetoxyacetyl chloride (13831-31-7) → 2-((4-iodophenyl)amino)-2-oxoethyl acetate

Conditions	Yield
In dichloromethane at 20℃; for 1.75h;	100%

3-methoxyphenylboronic acid (10365-98-7) + p-aminoiodobenzene (540-37-4) → 3'-methoxy-[1,1'-biphenyl]-4-amine (207287-79-4)

Conditions	Yield
With potassium carbonate In ethanol at 80℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water Suzuki Coupling; Inert atmosphere; Reflux;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Suzuki Coupling; Microwave irradiation;

rac-3-bromocyclohexene (1521-51-3) + p-aminoiodobenzene (540-37-4) → 4-bromo-N-(cyclohex-2-en-1-yl)aniline (1619252-25-3)

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 12h; Inert atmosphere;	100%

4-Phenyl-1-butyne (16520-62-0) + p-aminoiodobenzene (540-37-4) → 4-(4-phenylbut-1-yn-1-yl)aniline

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h; Reflux; Inert atmosphere;	100%

benzofuran-2-boronic acid (98437-24-2) + p-aminoiodobenzene (540-37-4) → 4-(benzofuran-2-yl)benzenamine (782-18-3)

Conditions	Yield
With sodium carbonate; dichlorobis(tri-O-tolylphosphine)palladium In 1,2-dimethoxyethane; ethanol; water at 125℃; for 2h;	99.5%

4-fluorobenzoyl chloride (403-43-0) + p-aminoiodobenzene (540-37-4) → 4-fluoro-N-(4-iodophenyl)-benzamide (326-03-4)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 1h;	99%

formic acid (64-18-6) + p-aminoiodobenzene (540-37-4) → N-(4-iodo-phenyl)-formamide (6393-17-5)

Conditions	Yield
With acetic anhydride In tetrahydrofuran; toluene at 15 - 20℃;	99%
With choline chloride*2SnCl2 at 70℃;	92%
With mesoporous silica SBA-15 functionalized with acidic [HNMP]ZnCl3 based deep eutectic solvent In neat (no solvent) at 20℃;	82%

p-aminoiodobenzene (540-37-4) → 1-azido-4-iodo-benzene (53694-87-4)

Conditions	Yield
Stage #1: p-aminoiodobenzene With trifluoroacetic acid; sodium nitrite at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 1h;	99%
Stage #1: p-aminoiodobenzene With hydrogenchloride In water at 0℃; Stage #2: With sodium nitrite In water for 0.166667h; Further stages;	98%
Stage #1: p-aminoiodobenzene With sodium nitrite In hydrogenchloride; ethanol at 0℃; for 0.25h; Stage #2: With sodium azide In hydrogenchloride; ethanol at 0℃; for 0.25h; Further stages.;	96%

trifluoroacetic anhydride (407-25-0) + p-aminoiodobenzene (540-37-4) → 2,2,2-trifluoro-N-(4-iodophenyl)acetamide (126063-08-9)

Conditions	Yield
In tetrahydrofuran for 0.666667h; Ambient temperature;	99%
In tetrahydrofuran at 20℃; for 1h;	98%
In dichloromethane for 1h; Ambient temperature;	78%
With pyridine In dichloromethane at 0℃; for 1h;
In tetrahydrofuran at 0 - 20℃; for 1h;

Upstream product

• 506-78-5 cyanogen iodide 
• 64-17-5 ethanol 
• 62-53-3 aniline 
• 636-98-6 p-nitrobenzene iodide 
• 2372-45-4 sodium butanolate 
• 71-43-2 benzene 
• 106-47-8 4-chloro-aniline 
• 98-50-0 p-aminophenylarsonic acid 
• 7664-93-9 sulfuric acid 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 64-19-7 acetic acid 
• 7732-18-5 water 
• 40643-37-6 1-(4'-Iodphenyl)-3-methyltriazen 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 94590-85-9 1-(4-iodophenyl)pyrrolidine-2,5-dione 
• 62134-54-7 N-(4-iodo-phenyl)-succinamic acid 
• 112687-14-6 benz[a]acridin-12-yl-(4-iodo-phenyl)-amine 
• 77774-39-1 1-(N-ethoxycarbonylamino)-4-iodobenzene 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 2898-46-6 N-(4-iodo-phenyl)-diacetamide 
• 962-09-4 N-(4-iodophenyl)-3-oxo-3-phenylpropanamide 
• 3381-47-3 N-benzylidene-4-iodoaniline 
• 52807-29-1 N-(4-iodophenyl)benzamide 
• 25759-84-6 1-(4-iodophenyl)-3-phenylthiourea 
• 5636-99-7 N,N'-bis(4-iodophenyl)formamidine 
• 63791-50-4 N-(4-iodophenyl)methylcarbamate 
• 2564-00-3 2-chloro-N-(4-iodophenyl)acetamide 
• 108757-32-0 N²-(4-iodo-phenyl)-[1,3,5]triazine-2,4-diyldiamine 

Relevant articles and documents

A facile reduction procedure for nitroarenes with Cp2TiCl2/Sm system

Nitroarenes can be reduced to the corresponding primary amines in good yields with Cp2TiCl2/Sm system under mild and neutral conditions.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

In situcreation of multi-metallic species inside porous silicate materials with tunable catalytic properties

Porous metal silicate (PMS) material PMS-11, consisting of uniformly distributed multi-metallic species inside the pores, is synthesized by using a discrete multi-metal coordination complex as the template, demonstrating high catalytic activity and selectivity in hydrogenation of halogenated nitrobenzenes by synergistically activating different reactant moleculesviaNi and Co transition metal centers, while GdIIILewis acid sites play a role in tuning the catalytic properties.