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
• Article Data: 3

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

General Description

Ethyl 2-amino-5-iodobenzoate, also known as EINECS 269-980-4 or NSC 233658, is an organic compound belonged to the family of Benzoic Acids and derivatives. It's exact structure includes an ethyl group, an amino group, and an iodine atom all attached to a benzoate backbone. The molecular weight of this compound is approximately 309.1 g/mol. Typically, it's used in various fields such as medicine, chemical research, and in the production of other compounds. The toxicological properties and safety measures of this compound have not been fully investigated, thus should be handled with caution.

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

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

Downstream Products

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

Relevant articles and documents

RE[N(SiMe3)2]3-Catalyzed Guanylation/Cyclization of Amino Acid Esters and Carbodiimides

The example of rare-earth metal-catalyzed guanylation/cyclization of amino acid esters and carbodiimides is well-established, forming 4(3H)-2-alkylaminoquinazolinones in 65-96% yields. The rare-earth metal amides RE[N(TMS)2]3 (RE = Y, Yb, Nd, Sm, La; TMS = SiMe3) showed high activities, and La[N(TMS)2]3 performed best for a wide scope of the substrates.

2-Substituted paullones: CDK1/cyclin B-inhibiting property and in vitro antiproliferative activity

9-Trifluoromethyl-paullones with a carbon chain in the 2-position were synthesized by palladium-catalyzed coupling reactions of a 2-iodoprecursor with terminal alkenes or alkynes, respectively. The introduction of a 2-cyanoethyl substituent led to a significant enhancement of CDK1/cyclin B inhibiting property and in vitro antiproliferative activity. (C) 2000 Elsevier Science Ltd. All rights reserved.