1-Aminomethyl-5-methoxyindane

1-Aminomethyl-5-methoxyindane is a chemical compound with the molecular formula C11H15NO. It is a member of the indane family, a group of bicyclic hydrocarbons that are part of the larger class of compounds known as terpenes. The compound is characterized by an indane backbone, which is a fused cyclohexane and benzene ring, with a methoxy group (-OCH3) and an aminomethyl group (-NHCH3) attached to the 5th and 1st carbon atoms, respectively.

Chemical Structure and Properties

The chemical structure of 1-Aminomethyl-5-methoxyindane consists of an indane backbone, which is a fused cyclohexane and benzene ring. Attached to the 5th carbon atom of the indane backbone is a methoxy group (-OCH3), which is an ether functional group consisting of a carbon atom bonded to an oxygen atom and a hydrogen atom. Attached to the 1st carbon atom of the indane backbone is an aminomethyl group (-NHCH3), which is an amine functional group consisting of a nitrogen atom bonded to a carbon atom and three hydrogen atoms.

The compound is a solid at room temperature and has a molar mass of 177.24 g/mol. It is soluble in organic solvents such as ethanol and dichloromethane, but is less soluble in water due to the presence of the nonpolar indane backbone and methoxy group.

Synthesis

The synthesis of 1-Aminomethyl-5-methoxyindane can be achieved through a multi-step process. The first step involves the reaction of indanone with a Grignard reagent to form a tertiary alcohol. This is followed by the conversion of the alcohol to a bromide using phosphorus tribromide. The bromide is then converted to an amine through nucleophilic substitution with ammonia. Finally, the amine is methylated using methyl iodide to form the final product.

Applications

While 1-Aminomethyl-5-methoxyindane is primarily used in research settings, it has potential applications in the pharmaceutical industry. Its chemical structure is similar to that of certain neurotransmitters, suggesting that it may have psychoactive properties. However, further research is needed to fully understand its potential uses and effects.

See Also

• Indane
• Methoxy Group
• Aminomethyl Group
• Grignard Reaction
• Nucleophilic Substitution