Ethyl 2-amino-5-iodobenzoate
[CAS# 268568-11-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 2-amino-5-iodobenzoate
• Synonyms: Ethyl 5-iodoanthranilate; 2-Amino-5-iodobenzoic acid ethyl ester
• Molecular Formula: C₉H₁₀INO₂
• Molecular Weight: 291.09
• CAS Registry Number: 268568-11-2
• EC Number: 608-010-2
• SMILES: CCOC(=O)C1=C(C=CC(=C1)I)N

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 69-71 ºC (Expl.)
• Index of Refraction: 1.63, Calc.^*
• Boiling Point: 347.9±32.0 ºC (760 mmHg), Calc.^*
• Flash Point: 164.2±25.1 ºC, Calc.^*

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

Ethyl 2-amino-5-iodobenzoate is an organic compound with the chemical formula C8H8INO2. It is an ester derivative of 2-amino-5-iodobenzoic acid, in which the carboxyl group (-COOH) is esterified with an ethyl group (-C2H5). This compound belongs to the class of halogenated aromatic compounds, and it is known for its utility in various chemical and pharmaceutical applications.

The discovery of ethyl 2-amino-5-iodobenzoate is tied to the broader interest in the synthesis and study of halogenated benzoic acid derivatives. These compounds have been investigated for their diverse chemical properties and their ability to participate in a variety of chemical reactions, making them valuable intermediates in organic synthesis. The presence of the amino group (-NH2) at position 2 and the iodine atom at position 5 of the benzene ring makes this compound an important structure in the development of more complex molecules.

Ethyl 2-amino-5-iodobenzoate is widely used in organic synthesis as a starting material or intermediate in the preparation of various bioactive compounds, including pharmaceuticals and agrochemicals. Its structure allows it to undergo a variety of chemical reactions, such as nucleophilic substitution, coupling reactions, and condensation reactions. The iodine atom, in particular, can participate in electrophilic aromatic substitution reactions, which are useful in the synthesis of other functionalized aromatic compounds.

One of the primary applications of ethyl 2-amino-5-iodobenzoate is in the synthesis of pharmaceutical compounds. The amino and iodine functional groups can be further modified or used to introduce specific pharmacophoric elements into a molecule, which can contribute to the biological activity of the resulting compound. This makes ethyl 2-amino-5-iodobenzoate a valuable intermediate in the synthesis of potential therapeutic agents.

Additionally, ethyl 2-amino-5-iodobenzoate can be used in the development of materials with specific electronic or optical properties. Its structure and reactivity make it suitable for incorporation into larger molecular frameworks or for the modification of existing materials to enhance their properties. In particular, its halogenated nature may contribute to the stability or reactivity of materials used in electronic devices, sensors, or other advanced technologies.

In conclusion, ethyl 2-amino-5-iodobenzoate is a versatile chemical compound with significant applications in organic synthesis, particularly in the development of pharmaceuticals and specialty chemicals. Its functional groups make it an important intermediate in the synthesis of bioactive compounds, and its halogenated structure offers opportunities for further chemical modifications.