4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester
[CAS# 1256584-74-3]

Identification

• Classification: API >> Antineoplastic agents
• Name: 4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester
• Synonyms: tert-butyl 4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoate
• Molecular Formula: C₁₈H₂₅IO₃
• Molecular Weight: 416.29
• CAS Registry Number: 1256584-74-3
• SMILES: CCC1=C(C=C(C=C1)C(C)(C)C(=O)CC(=O)OC(C)(C)C)I

Properties

• Solubility: Insoluble (5.8E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.339±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester is a notable compound in organic chemistry, recognized for its diverse applications in chemical synthesis and medicinal chemistry. This molecule features a complex structure that includes an iodinated aromatic ring, a beta-oxobutanoic acid moiety, and a tert-butyl ester group, each contributing to its unique chemical properties and potential uses.

The compound was discovered as part of research aimed at developing new reagents and intermediates for organic synthesis. The 4-ethyl-3-iodo substitution pattern on the aromatic ring is particularly significant. Iodine, being a highly reactive halogen, can participate in various chemical reactions, such as nucleophilic substitutions and cross-coupling reactions. The ethyl group provides additional steric hindrance, influencing the reactivity and selectivity of the molecule in these reactions.

The gamma,gamma-dimethyl-beta-oxobutanoic acid component introduces a beta-keto acid functionality to the molecule. Beta-keto acids are important in organic synthesis due to their ability to form various derivatives through reactions such as decarboxylation and condensation. The presence of two methyl groups at the gamma position enhances the compound's stability and solubility, making it a useful intermediate in the synthesis of more complex molecules.

The 1,1-dimethylethyl ester group is another critical feature of this compound. Tert-butyl esters are commonly used in organic chemistry to protect carboxyl groups during synthesis. They can be easily hydrolyzed under mild conditions to reveal the free carboxyl group, which can then participate in further chemical reactions. This property makes the compound a versatile reagent for constructing complex molecules with various functional groups.

One of the key applications of 4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester is in the synthesis of pharmaceuticals. The iodine atom on the aromatic ring facilitates cross-coupling reactions, which are commonly used to form carbon-carbon bonds in drug discovery. By using this compound as a starting material, researchers can create a wide range of drug-like molecules with diverse biological activities. The beta-keto acid functionality allows for further modifications that can enhance the pharmacological properties of the resulting compounds.

In addition to its use in drug synthesis, this compound has applications in material science. The ability to introduce various functional groups through chemical transformations makes it suitable for developing new materials with specific properties. For example, it can be used to create polymers or functionalized organic materials that have applications in electronics or sensing technologies.

The synthesis of 4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester involves multiple steps, including the introduction of the iodinated aromatic ring and the formation of the beta-keto acid structure. The tert-butyl ester group is typically introduced through esterification reactions, which provide a stable protecting group that can be removed when needed.

Overall, 4-Ethyl-3-iodo-gamma,gamma-dimethyl-beta-oxobenzenebutanoic acid 1,1-dimethylethyl ester is a valuable compound in organic synthesis and materials science. Its unique structure and functional groups make it a versatile reagent for developing new drugs and materials with specific properties. Ongoing research and development in this area are expected to reveal further applications and potential benefits of this compound in various fields.