29632-74-4

Basic information

• Product Name: 2-Fluoro-4-iodoaniline
• Synonyms: 2-FLUORO-4-IODOANILINE;2-FLUORO-4-IODOBENZENAMINE;2-Fluoro-4-idioaniline;2-FLUORO-4-IODO-PHENYLAMINE;2-Fluoro-4-iodoaniline 98%;2-Fluoro-4-iodoaniline98%;2-Fluoro-4-iodoanili;2-fluo-4-iodoaniline
• CAS NO: 29632-74-4
• Molecular Formula: C₆H₅FIN
• Molecular Weight: 237.01
• Product Categories: Fluorobenzene;Fluoro-Aromatics;Benzene series;Aniline;Miscellaneous;Anilines, Amides & Amines;Fluorine Compounds;Iodine Compounds;Benzenes;Amines;C2 to C6;Nitrogen Compounds;amine| alkyl Fluorine| alkyl Iodine
• Mol File: 29632-74-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 55-57 °C(lit.)
• Boiling Point: 248.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Off-white to brown/Powder
• Density: 2.008 g/cm³
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Refrigerated.
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 2.41±0.10(Predicted)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• BRN: 2081100
• CAS DataBase Reference: 2-Fluoro-4-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-4-iodoaniline(29632-74-4)
• EPA Substance Registry System: 2-Fluoro-4-iodoaniline(29632-74-4)

Safety Data

• Hazard Codes: Xi,T,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39-26/37/39
• RIDADR: PG3
• WGK Germany: 3
• HazardClass: IRRITANT-HARMFUL, LIGHT SENSITIV
• Hazardous Substances Data: 29632-74-4(Hazardous Substances Data)

Usage

Chemical Properties

off-white to brown powder

Uses

2-Fluoro-4-iodoaniline is widely used in the pharmaceutical, chemical and food industries as a fundamental building block to create a variety of important compounds.

General Description

The profiling of iodine-containing metabolites produced by the earthworm Eisenia veneta by exposing it to 2-fluoro-4-iodoaniline was carried out using high-performance liquid chromatography/inductively coupled plasma mass spectrometry (HPLC/ICPMS).

InChI:InChI=1/C6H5FIN/c7-5-2-1-4(8)3-6(5)9/h1-3H,9H2

Synthetic route

2-Fluoroaniline (348-54-9) → 2-fluro-4-iodoaniline (29632-74-4)

Conditions	Yield
With iodine; sodium hydrogencarbonate In water at 60 - 80℃; for 2h;	77%
With iodine; sodium hydrogencarbonate In water at 60℃; for 3h;	76%
Stage #1: 2-Fluoroaniline With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Stage #2: With poly[4-(dibutyliodostannyl)butyl]styrene In diethyl ether; hexane at 20℃; for 18h; Stage #3: With Iodine monochloride In diethyl ether; hexane at -78 - 20℃;	67%

2-fluro-4-iodoaniline (29632-74-4) + trimethylsilylacetylene (1066-54-2) → 2-fluoro-4-((trimethylsilyl)ethynyl)aniline (518342-58-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 21h; Sonogashira Cross-Coupling; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 15h; Sonogashira Coupling;	88%

4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid (867130-26-5) + 2-fluro-4-iodoaniline (29632-74-4) → 4-(2-fluoro-4-iodophenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (934664-24-1)

Conditions	Yield
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;	100%
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4.08333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;	100%
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4.08333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;	100%

thiophosgene (463-71-8) + 2-fluro-4-iodoaniline (29632-74-4) → 2-fluoro-4-iodo-1-isothiocyanatobenzene (945530-32-5)

Conditions	Yield
In chloroform; water at 20℃; for 16h;	100%
In chloroform; water at 20℃; for 16h;	100%
In dichloromethane; water at 20℃;	96.8%

formaldehyd (50-00-0) + 2-fluro-4-iodoaniline (29632-74-4) → N-(4-iodo-2-fluorophenyl)formamide (791112-16-8)

Conditions	Yield
With acetic anhydride In tetrahydrofuran; toluene at 20℃;	100%

2-fluro-4-iodoaniline (29632-74-4) + sodium O-ethyl dithiocarbonate (140-90-9) → 6-iodobenzo[d]thiazole-2-thiol (54420-94-9)

Conditions	Yield
In N,N-dimethyl-formamide at 95℃; for 5h;	100%

2-fluro-4-iodoaniline (29632-74-4) + 2,3,4,-trifluorobenzoic acid (61079-72-9) → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzoic acid (391211-97-5)

Conditions	Yield
With lithium amide In tetrahydrofuran	99%
With lithium amide In N,N-dimethyl-formamide Inert atmosphere;	85%
With lithium amide In tetrahydrofuran at 45 - 55℃; for 1.25 - 2.5h; Product distribution / selectivity;	80%

2-fluro-4-iodoaniline (29632-74-4) → 1-azido-2-fluoro-4-iodobenzene (945559-14-8)

Conditions	Yield
Stage #1: 2-fluro-4-iodoaniline With trifluoroacetic acid; sodium nitrite at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 1h;	99%
Stage #1: 2-fluro-4-iodoaniline With hydrogenchloride; sodium nitrite In water at -5℃; for 0.5h; Stage #2: With sodium azide In water at -5℃; for 1h;	97%

sodium cyclopropylsulfinate (910209-21-1) + 2-fluro-4-iodoaniline (29632-74-4) → C9H10FNO2S (1147558-09-5)

Conditions	Yield
With N,N`-dimethylethylenediamine; copper (I) trifluoromethane sulfonate benzene In dimethyl sulfoxide at 120℃; for 16h;	99%
copper(I) trifluoromethanesulfonate benzene complex; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 120℃; for 16h;	99%
With N,N`-dimethylethylenediamine; copper(I) trifluoromethanesulfonate benzene In dimethyl sulfoxide at 120℃; for 16h;	99%

2-fluro-4-iodoaniline (29632-74-4) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(2-fluoro-4-iodophenyl)cyclopropanecarboxamide (1061683-60-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	99%

2-fluro-4-iodoaniline (29632-74-4) + 1,1'-carbonyldiimidazole (530-62-1) → 1-(2-fluoro-4-iodophenyl)urea (871700-48-0)

Conditions	Yield
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In chloroform at 0 - 20℃; for 4.25h; Stage #2: With ammonia In chloroform; water at 0 - 20℃; for 1.5h;	98.8%
With triethylamine In chloroform at 0 - 30℃; for 4h; Inert atmosphere;
With triethylamine In chloroform at 0 - 20℃; for 4.25h;

2-fluro-4-iodoaniline (29632-74-4) + 2,5-hexanedione (110-13-4) → 1-(2-fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole (217314-30-2)

Conditions	Yield
toluene-4-sulfonic acid In toluene for 1h; Heating / reflux;	98%
With toluene-4-sulfonic acid In toluene at 110℃; for 1h;	49%
With p-toluenesulfonic acid monohydrate In toluene at 110℃; for 1h; Dean-Stark;	67.5 g

2-fluro-4-iodoaniline (29632-74-4) + methanesulfonyl chloride (124-63-0) → 2-fluoro-4-iodo-1-methanesulfonylaminobenzene (143937-74-0)

Conditions	Yield
With pyridine at 20℃; for 2h;	98%
In pyridine at 20℃; for 2h;	98%
With pyridine at 20℃; for 2h;	95%

2-fluro-4-iodoaniline (29632-74-4) → 2-fluoro-4-iodobenzenediazonium tetrafluoroborate

Conditions	Yield
With tert.-butylnitrite; boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether at -10 - 0℃;	98%

2-fluro-4-iodoaniline (29632-74-4) + C14H9F3O2 → C20H13F3INO2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 60℃; for 6h;	97.6%

formic acid (64-18-6) + 2-fluro-4-iodoaniline (29632-74-4) → N-(4-iodo-2-fluorophenyl)formamide (791112-16-8)

Conditions	Yield
Stage #1: formic acid; 2-fluro-4-iodoaniline With acetic anhydride In tetrahydrofuran; toluene at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; toluene	97%

tetrahydrofuran-2-carbonyl chloride (52449-98-6) + 2-fluro-4-iodoaniline (29632-74-4) → tetrahydro-furan-2-carboxylic acid (2-fluoro-4-iodophenyl)amide (641612-64-8)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 18h;	96%
With dmap In dichloromethane

2-fluro-4-iodoaniline (29632-74-4) + phenylacetylene (536-74-3) → 2-fluoro-4-phenylethynyl-phenylamine (1241745-70-9)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; for 18h; Inert atmosphere;	95%

2-fluro-4-iodoaniline (29632-74-4) + tetramethylammonium trifluoromethylselenate(0) (75264-92-5) → 1-amino-2-fluoro-4-[(trifluoromethyl)seleno]benzene (15946-31-3)

Conditions	Yield
With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 40℃; for 24h; Glovebox; Inert atmosphere;	95%

morpholine-3-one (109-11-5) + 2-fluro-4-iodoaniline (29632-74-4) → 4-(4-amino-3-fluoro-phenyl)-morpholin-3-one (742073-22-9)

Conditions	Yield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 160℃; under 4500.45 - 5250.53 Torr; for 2h; Ullmann-Goldberg Substitution; Microwave irradiation;	94%
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux; Inert atmosphere;	74%
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux; Inert atmosphere;	74%
With potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 140℃; for 2h; microwave;	33%
With copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 16h;

2-fluro-4-iodoaniline (29632-74-4) + 3-fluoroisonicotinic acid (393-53-3) → 3-((2-fluoro-4-iodophenyl)amino)isonicotinic acid (885588-03-4)

Conditions	Yield
Stage #1: 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at -55℃; Inert atmosphere; Stage #2: 3-fluoroisonicotinic acid In tetrahydrofuran at 20℃; for 96h; Stage #3: With hydrogenchloride In water pH=2;	94%
Stage #1: 2-fluro-4-iodoaniline; 3-fluoroisonicotinic acid With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran for 1h; Product distribution / selectivity;	33%
Stage #1: 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at -67 - -59℃; for 2.5h; Inert atmosphere; Stage #2: 3-fluoroisonicotinic acid In tetrahydrofuran for 96h;

2,3,4-trifluoro-5-vinylbenzoic acid (848852-32-4) + 2-fluro-4-iodoaniline (29632-74-4) → 3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-vinylbenzoic acid (848852-33-5)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃;	94%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 5.75h; Inert atmosphere;	94%
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;	35%

pent-2-ynoic acid (5963-77-9) + 2-fluro-4-iodoaniline (29632-74-4) → 4-(4-ethyl-1H-1,2,3-triazol-1-yl)-2-fluoroaniline (1276538-16-9)

Conditions	Yield
With sodium azide; copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; potassium carbonate; L-proline In water; dimethyl sulfoxide at 65℃;	94%

2-fluro-4-iodoaniline (29632-74-4) + diisopropyl-carbodiimide (693-13-0) → 2-(2-fluoro-4-iodophenyl)-1,3-diisopropylguanidine (1436412-58-6)

Conditions	Yield
at 130℃; for 15h; Inert atmosphere;	94%
With dichloro bis(acetonitrile) palladium(II) In toluene at 130℃; under 1500.15 Torr; for 16h; Inert atmosphere;	72%

NH-pyrazole (288-13-1) + 2-fluro-4-iodoaniline (29632-74-4) → 2-fluoro-4-(1H-pyrazol-1-yl)aniline (1147557-79-6)

Conditions	Yield
With copper(l) iodide; 8-quinolinol; potassium carbonate In dimethylsulfoxide-d6 at 120℃; for 16h; Inert atmosphere;	94%
With copper(l) iodide; caesium carbonate; trans-1,2-cyclohexanediamine In 1,2-dimethoxyethane at 25 - 86℃; for 72.3333h; Inert atmosphere;	650 g

2-fluro-4-iodoaniline (29632-74-4) + tri-n-butyl(vinyl)tin (7486-35-3) → 2-fluoro-4-vinylaniline

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 1h;	93%
tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methyl-phenol In toluene at 100℃; for 1h;	93%

(R)-5-chloro-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-8-methylpyrido[2,3-d]pyrimidine-4,7-(3H,8H)-dione (1227054-00-3) + 2-fluro-4-iodoaniline (29632-74-4) → (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido-[2,3-d]pyrimidine-4,7(3H,8H)-dione (1227054-01-4)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -5 - 20℃; Large scale;	93%
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 85℃; for 2h; Product distribution / selectivity; De-gassed solvent;

2-fluro-4-iodoaniline (29632-74-4) + 1,1'-carbonyldiimidazole (530-62-1) + methylamine (74-89-5) → N-(2-fluoro-4-iodophenyl)-N'-methylurea (871700-37-7)

Conditions	Yield
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: methylamine In water; N,N-dimethyl-formamide at 0 - 20℃;	93%
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: methylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 1h;	93%
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: methylamine In methanol; N,N-dimethyl-formamide at 0 - 20℃;	92%

2-fluro-4-iodoaniline (29632-74-4) + acetic anhydride (108-24-7) → N-(2-fluoro-4-iodo-phenyl)-acetamide (97760-94-6)

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2.16667h;	92%
In tetrahydrofuran at 0 - 25℃; for 2.16667h;	92%
In tetrahydrofuran at 0 - 25℃; for 2.16667h;	92%

pyridine-2-thione (2637-34-5) + 2-fluro-4-iodoaniline (29632-74-4) → 2-fluoro-4-(pyridin-2-ylsulfanyl)-phenylamine

Conditions	Yield
With 8-quinolinol; copper(l) iodide In dimethyl sulfoxide at 130℃;	92%

3-Methyl-1H-pyridin-2-one (1003-56-1) + 2-fluro-4-iodoaniline (29632-74-4) → 1-(4-amino-3-fluorophenyl)-3-methylpyridin-2(1H)-one

Conditions	Yield
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate In tert-Amyl alcohol at 100℃; for 5h; Inert atmosphere; Glovebox;	92%
With 8-quinolinol; copper(l) iodide In dimethyl sulfoxide at 130℃;	78%

Upstream product

• 348-54-9 2-Fluoroaniline 

Downstream Products

• 97760-94-6 N-(2-fluoro-4-iodo-phenyl)-acetamide 
• 217314-30-2 1-(2-fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole 
• 754193-46-9 2-fluoro-4-[2-ethylimidazol-1-yl]aniline 
• 540510-47-2 1-(4-amino-3-fluorophenyl)-2-hydroxymethylimidazole 
• 754193-47-0 2-fluoro-4-[2-isopropylimidazol-1-yl]aniline 
• 865878-91-7 N-(2-fluoro-4-iodo-phenyl)-2-methoxy-acetamide 
• 540510-44-9 [1-(4-amino-3-fluorophenyl)-1H-imidazol-2-ylmethyl]methylcarbamic acid benzyl ester 
• 335275-99-5 2-(3-cyano-4-fluorophenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (2-fluoro-4-iodophenyl)amide 
• 63069-50-1 4-cyano-2-fluoroaniline 
• 865878-87-1 methyl N-(2-fluoro-4-iodophenyl)carbamate 
• 865878-85-9 2,2,2-trifluoro-N-(2-fluoro-4-iodo-phenyl)-acetamide 

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