the reactions of amines and it's solubility

Question

How does the solubility in water differ for the nitrogen containing compounds? Suggest reasons for this.What would you expect the solubility in non-aqueous solvents to be? Does your answer to this suggest any extra precautions that should be taken when working with amines?

Answer 1

Hydrogen bonding increases the chance of solubility in water. Hence, primary amine would be more likely soluble than secondary, and tertiary amine (due to no N-H bond) would likely to be insoluble. 

 

Answer 2

The order of amine water-solubility decreases with the degree of substitution. The order is exactly reversed when compared to non-polar solvent solubility. 

 

The trends are explained by the level of hydrophobicity and decrease in hydrogen bonding for the various amines.

 

Amines are mildly toxic substances, but can also be flammable because of the possibility of high hydrocarbon content. You must ensure no open flames are near the area where you handle these substances.