Tert-Butanesulfinamide

Tert-Butanesulfinamide is an organic compound used in the field of organic chemistry. It is a white, crystalline solid that is soluble in water and most organic solvents. It is primarily used as a chiral auxiliary in the synthesis of other organic compounds.

Structure and Properties

Tert-Butanesulfinamide is a sulfonamide derivative, which means it contains a sulfur atom bonded to two oxygen atoms and one nitrogen atom. The molecule also contains a tertiary butyl group, which gives it its name. The presence of the sulfur atom gives the compound its unique properties, including its ability to act as a chiral auxiliary.

The compound's molecular formula is C4H11NOS, and its molecular weight is 121.20 g/mol. It has a melting point of 66-68 °C and a boiling point of 76-78 °C at 760 mmHg.

Synthesis

Tert-Butanesulfinamide can be synthesized from tert-butylamine and sulfinyl chloride in the presence of a base. The reaction proceeds via a nucleophilic substitution mechanism, with the amine acting as the nucleophile and the sulfinyl chloride as the electrophile.

Applications

Tert-Butanesulfinamide is primarily used as a chiral auxiliary in the synthesis of other organic compounds. A chiral auxiliary is a compound that is temporarily incorporated into an organic synthesis process in order to control the stereochemical outcome of the reaction. In the case of tert-butanesulfinamide, it is used to control the formation of chiral centers in the resulting product.

Safety

Like many organic compounds, tert-butanesulfinamide should be handled with care. It can cause irritation to the skin and eyes, and may be harmful if swallowed or inhaled. Appropriate safety measures should be taken when handling this compound, including the use of personal protective equipment.