268568-11-2

Basic information

• Product Name: Ethyl 2-amino-5-iodobenzoate
• Synonyms: Ethyl 2-amino-5-iodobenzoate, 98+%;Ethyl 5-iodoanthranilate;Ethyl 2-amino-5-iodobenzoate;2-Amino-5-iodobenzoic acid ethyl ester;Ethyl 5-iodoanthranilate, 2-(Ethoxycarbonyl)-4-iodoaniline;2-amino-5-iodobenzoate
• CAS NO: 268568-11-2
• Molecular Formula: C₉H₁₀INO₂
• Molecular Weight: 291.09
• EINECS: 1312995-182-4
• Product Categories: Acids & Esters;Anilines, Amides & Amines;Iodine Compounds
• Mol File: 268568-11-2.mol

Chemical Properties

• Melting Point: 69-71°C
• Boiling Point: 347.9 °C at 760 mmHg
• Flash Point: 164.2 °C
• Appearance: pale yellow crystalline powder
• Density: 1.730
• Vapor Pressure: 5.23E-05mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.86±0.10(Predicted)
• CAS DataBase Reference: Ethyl 2-amino-5-iodobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-amino-5-iodobenzoate(268568-11-2)
• EPA Substance Registry System: Ethyl 2-amino-5-iodobenzoate(268568-11-2)

Safety Data

• Hazardous Substances Data: 268568-11-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-amino-5-iodobenzoate is used as an intermediate compound for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Research:
Ethyl 2-amino-5-iodobenzoate is used as a research compound in chemical laboratories, aiding in the investigation of chemical reactions, properties, and potential applications in various fields.
Used in Production of Other Compounds:
Ethyl 2-amino-5-iodobenzoate is used as a precursor in the synthesis of other organic compounds, playing a crucial role in the chemical industry for the creation of new materials and products.

InChI:InChI=1/C9H10INO2/c1-2-13-9(12)7-5-6(10)3-4-8(7)11/h3-5H,2,11H2,1H3

Synthetic route

2-ethoxycarbonylaniline (87-25-2) → ethyl 2-amino-5-iodobenzoate (268568-11-2)

Conditions	Yield
With iodine; silver sulfate In ethanol at 20℃; for 1h;	90%

ethanol (64-17-5) + 2-amino-5-iodobenzoic acid (5326-47-6) → ethyl 2-amino-5-iodobenzoate (268568-11-2)

Conditions	Yield
With hydrogenchloride for 7h; Esterification; Heating;
With thionyl chloride for 18h; Reflux; Inert atmosphere; Cooling with ice;

ethyl 2-amino-5-iodobenzoate (268568-11-2) + trimethylsilylacetylene (1066-54-2) → 2-amino-5-trimethylsilanylethynyl-benzoic acid ethyl ester (870621-97-9)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In triethylamine at 50℃; for 4h;	90%

ethyl 2-amino-5-iodobenzoate (268568-11-2) + diisopropyl-carbodiimide (693-13-0) → 6-iodo-3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one

Conditions	Yield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Schlenk technique; Inert atmosphere;	86%

thiophene-2-carbonitrile (1003-31-2) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 2-amino-5-(5-cyanothiophen-2-yl)benzoate (1397709-67-9)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	77%

tributyl-amine (102-82-9) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 2-amino-5-butyrylbenzoate (1290542-74-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); tetrabutylammomium bromide; water; zinc(II) oxide In dimethyl sulfoxide at 100℃; for 36h;	76%

2-isobutylthiazole (18640-74-9) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 2-amino-5-(2-isobutylthiazol-5-yl)-benzoate (1397709-71-5)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	73%

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 5-(4-amino-3-ethoxycarbonylphenyl)-2-methylthiazole- (1397709-72-6)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	72%

N-Methylpyrrole (96-54-8) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 2-amino-5-(1-methylpyrrol-2-yl)benzoate (1397709-70-4)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	64%

1-(4-chlorothiophen-2-yl)ethan-1-one (34730-20-6) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 5-(5-acetyl-3-chlorothiophen-2-yl)-2-aminobenzoate (1397709-68-0)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	61%

methyl 2-methyl-3-furancarboxylate (6141-58-8) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → methyl 5-(4-amino-3-ethoxycarbonylphenyl)-2-methylfuran-3-carboxylate (1397709-69-1)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Inert atmosphere;	60%

ethyl 2-amino-5-iodobenzoate (268568-11-2) + 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (85006-31-1) → 3-amino-5-(4-amino-3-ethoxycarbonyl-phenyl)-4-methylthiophene-2-carboxylic acid methyl ester (1393718-89-2)

Conditions	Yield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;	42%

ethyl 3-(chloroformyl)propionate (14794-31-1) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → 2-(3-ethoxycarbonyl-propionylamino)-5-iodo-benzoic acid ethyl ester (268568-12-3)

Conditions	Yield
With pyridine In toluene for 2h; Acylation; Heating;

pyrrolidine (123-75-1) + ethyl 2-amino-5-iodobenzoate (268568-11-2) → 1-(2-carbethoxy-4-iodophenylazo)pyrrolidine

Conditions	Yield
Stage #1: ethyl 2-amino-5-iodobenzoate With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: pyrrolidine With potassium carbonate In water; acetonitrile at 0 - 20℃; Further stages.;

ethyl 2-amino-5-iodobenzoate (268568-11-2) → C14H17N3O3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 2.2: 85 percent / tetrahydrofuran / -40 - 20 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → ethyl 2-azido-5-formyl-benzoate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 2.2: 85 percent / tetrahydrofuran / -40 - 20 °C 3.1: 94 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 20 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → C42H48N2O8

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / CuI / Pd(PPh3)4 / triethylamine / 4 h / 50 °C 2: 86 percent / triethylamine / CHCl3 / 2 h / Heating 3: 96 percent / K2CO3 / CH2Cl2; methanol / 3 h / 20 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → C48H64N2O8Si2 (870621-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / CuI / Pd(PPh3)4 / triethylamine / 4 h / 50 °C 2: 86 percent / triethylamine / CHCl3 / 2 h / Heating View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (252894-39-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / toluene / 2 h / Heating 2: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3: aq. DMSO / 3 h / 150 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 5-hydroxy-7-iodo-2-oxo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester (268568-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / toluene / 2 h / Heating 2: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 2-iodo,9-trifluoromethyl-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one (252894-28-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 3-(6-oxo-9-trifluoromethyl-5,6,7,12-tetrahydro-indolo[3,2-d][1]benzazepin-2-yl)-acrylonitrile (309967-45-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: Pd(OAc)2; P(C6H5)3; TEA / dimethylformamide / Heating View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 3-(6-oxo-9-trifluoromethyl-5,6,7,12-tetrahydro-benzo[2,3]azepino[4,5-b]indol-2-yl)-acrylic acid methyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: Pd(OAc)2; P(C6H5)3; TEA / dimethylformamide / Heating View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 2-(3-hydroxy-prop-1-ynyl)-9-trifluoromethyl-5,12-dihydro-7H-benzo[2,3]azepino[4,5-b]indol-6-one

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: PdCl2[P(C6H5)3]2; CuI; TEA / 50 °C View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 2-(3-oxo-1-butenyl)-9-trifluoromethyl-7,12-dihydro-indolo[3, 2-d][1]benzazepin-6(5H)-one

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: Pd(OAc)2; P(C6H5)3; TEA / dimethylformamide / Heating View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 3-(6-oxo-9-trifluoromethyl-5,6,7,12-tetrahydro-indolo[3,2-d][1]benzazepin-2-yl)-propionitrile

Conditions	Yield
Multi-step reaction with 6 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: Pd(OAc)2; P(C6H5)3; TEA / dimethylformamide / Heating 6.1: Mg; MeOH / 1 h / Heating View Scheme

ethyl 2-amino-5-iodobenzoate (268568-11-2) → 98 N 349

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / toluene / 2 h / Heating 2.1: KH / dimethylformamide; toluene / 3 h / 0 - 80 °C 3.1: aq. DMSO / 3 h / 150 °C 4.1: AcOH / 1 h / 70 °C 4.2: H2SO4; AcOH / 1 h / 70 °C 5.1: PdCl2[P(C6H5)3]2; CuI; TEA / 50 °C View Scheme

Upstream product

• 87-25-2 2-ethoxycarbonylaniline 
• 64-17-5 ethanol 
• 5326-47-6 2-amino-5-iodobenzoic acid 

Downstream Products

• 268568-12-3 2-(3-ethoxycarbonyl-propionylamino)-5-iodo-benzoic acid ethyl ester 
• 1397709-68-0 ethyl 5-(5-acetyl-3-chlorothiophen-2-yl)-2-aminobenzoate 
• 1397709-71-5 ethyl 2-amino-5-(2-isobutylthiazol-5-yl)-benzoate 
• 1397709-69-1 methyl 5-(4-amino-3-ethoxycarbonylphenyl)-2-methylfuran-3-carboxylate 
• 1397709-72-6 ethyl 5-(4-amino-3-ethoxycarbonylphenyl)-2-methylthiazole- 
• 1397709-67-9 ethyl 2-amino-5-(5-cyanothiophen-2-yl)benzoate 
• 1397709-70-4 ethyl 2-amino-5-(1-methylpyrrol-2-yl)benzoate 
• 1290542-74-3 ethyl 2-amino-5-butyrylbenzoate 
• 252894-30-7 3-(6-oxo-9-trifluromethyl-5,6,7,12-tetrahydro-indolo[3,2-d]benzazepin-2-yl)-propionitrile 
• 870621-98-0 C₄₈H₆₄N₂O₈Si₂ 
• 870621-97-9 2-amino-5-trimethylsilanylethynyl-benzoic acid ethyl ester 

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