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

Description

Ethyl 2-chloro-5-iodobenzoate is an organic chemical compound characterized by the molecular formula C9H8ClIO2. It is a derivative of benzoic acid, featuring a chlorine and iodine atom along with an ester group. Ethyl 2-chloro-5-iodobenzoate is recognized for its versatility in organic synthesis and as a key intermediate in a variety of chemical reactions, particularly in the production of pharmaceuticals, agrochemicals, and other fine chemicals. The presence of the 2-chloro-5-iodobenzoate group in its structure offers a flexible platform for additional functionalization, establishing it as a significant building block in the realm of organic chemistry. Furthermore, its reactivity and distinctive properties render it a crucial reagent in chemical research and development.

Uses

Used in Pharmaceutical Industry:
Ethyl 2-chloro-5-iodobenzoate is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structural features and reactivity make it an essential component in the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, Ethyl 2-chloro-5-iodobenzoate serves as a vital intermediate for the production of agrochemicals. Its properties contribute to the creation of effective and targeted pest control agents and other agricultural products.
Used in Organic Synthesis:
Ethyl 2-chloro-5-iodobenzoate is employed as a versatile building block in organic synthesis. Its functional groups and reactivity allow for the construction of complex organic molecules, facilitating the development of novel chemical entities.
Used in Chemical Research and Development:
As a significant reagent in the field of chemical research and development, Ethyl 2-chloro-5-iodobenzoate is used to explore new reaction pathways, investigate the properties of novel compounds, and advance the understanding of chemical processes. Its unique characteristics make it an indispensable tool for researchers in the chemical sciences.

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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