289039-54-9

Basic information

• Product Name: ETHYL 2-CHLORO-5-IODOBENZOATE
• Synonyms: ETHYL 2-CHLORO-5-IODOBENZOATE;2-Chloro-5-iodobenzoic acid, ethyl ester
• CAS NO: 289039-54-9
• Molecular Formula: C₉H₈ClIO₂
• Molecular Weight: 310.52
• Product Categories: Acids & Esters;Chlorine Compounds;Iodine Compounds
• Mol File: 289039-54-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 328.7 °C at 760 mmHg
• Flash Point: 152.6 °C
• Appearance: /
• Density: 1.745 g/cm³
• Vapor Pressure: 0.000186mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: ETHYL 2-CHLORO-5-IODOBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CHLORO-5-IODOBENZOATE(289039-54-9)
• EPA Substance Registry System: ETHYL 2-CHLORO-5-IODOBENZOATE(289039-54-9)

Safety Data

• Hazardous Substances Data: 289039-54-9(Hazardous Substances Data)

Usage

General Description

Ethyl 2-chloro-5-iodobenzoate is an organic chemical compound with the molecular formula C9H8ClIO2. It is derived from benzoic acid and contains a chlorine and iodine atom, as well as an ester group. Ethyl 2-chloro-5-iodobenzoate is commonly used in organic synthesis and as an intermediate in various chemical reactions. It is often used in the production of pharmaceuticals, agrochemicals, and other fine chemicals. The 2-chloro-5-iodobenzoate group within the molecule provides a versatile platform for further functionalization, making it a valuable building block in organic chemistry. Additionally, its reactivity and unique properties make it an important reagent in the field of chemical research and development.

InChI:InChI=1/C9H8ClIO2/c1-2-13-9(12)7-5-6(11)3-4-8(7)10/h3-5H,2H2,1H3

Synthetic route

ethanol (64-17-5) + 2-chloro-5-iodobenzoic acid (19094-56-5) → ethyl 2-chloro-5-iodobenzoate (289039-54-9)

Conditions	Yield
With hydrogenchloride In water for 12h; Reflux;	1.74 g

4-bromo-1H-pyrazole (2075-45-8) + ethyl 2-chloro-5-iodobenzoate (289039-54-9) → ethyl 5-(4-bromopyrazol-1-yl)-2-chlorobenzoate

Conditions	Yield
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 1h; Inert atmosphere; Reflux;	1.41 g
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 1h; Inert atmosphere; Reflux;	1.41 g

ethyl 2-chloro-5-iodobenzoate (289039-54-9) → ethyl 2-chloro-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-1-yl]benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / isopropyl alcohol / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / isopropyl alcohol; water / Inert atmosphere; Reflux View Scheme

ethyl 2-chloro-5-iodobenzoate (289039-54-9) → 2-chloro-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-1-yl]benzoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / isopropyl alcohol / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / isopropyl alcohol; water / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux View Scheme

ethyl 2-chloro-5-iodobenzoate (289039-54-9) → 2-chloro-N-cyclopropyl-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-1-yl]benzamide

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / isopropyl alcohol / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux 4: thionyl chloride / toluene / 2 h / 80 °C 5: dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / isopropyl alcohol; water / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux 4: thionyl chloride / toluene / 2 h / 80 °C 5: dichloromethane / 2 h / 20 °C View Scheme

ethyl 2-chloro-5-iodobenzoate (289039-54-9) → 2-chloro-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-1-yl]benzoic acid chloride

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / isopropyl alcohol / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux 4: thionyl chloride / toluene / 2 h / 80 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 2: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / isopropyl alcohol; water / Inert atmosphere; Reflux 3: sodium hydroxide; methanol / 3 h / Reflux 4: thionyl chloride / toluene / 2 h / 80 °C View Scheme

ethyl 2-chloro-5-iodobenzoate (289039-54-9) → 2-chloro-5-(cyclopropylethynyl) benzoic acid (1346141-19-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 13 h / 20 °C 2: sodium hydroxide; water / ethanol / 15 h / 20 °C View Scheme

Cyclopropylacetylene (6746-94-7) + ethyl 2-chloro-5-iodobenzoate (289039-54-9) → ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1346141-18-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 13h;	1.26 g

Upstream product

• 64-17-5 ethanol 
• 19094-56-5 2-chloro-5-iodobenzoic acid 

Downstream Products

• 1346141-19-2 2-chloro-5-(cyclopropylethynyl) benzoic acid 
• 1346141-18-1 ethyl 2-chloro-5-(cyclopropylethynyl)benzoate 

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