What Is Azetidine?
Azetidine is a saturated tetracyclic heterocyclic compound with the chemical formula C3H7N.
The CAS number is 503-29-7, and its other names include trimethyleneimine, azacyclobutane, and 1,3-propyleneimine.
Azetidine is classified as a flammable liquid and skin corrosive/irritant in the GHS classification. Azetidine is classified as a hazardous and flammable substance under the Industrial Safety and Health Law and as a Class 4 Petroleum No. 1 under the Fire Service Law.
Uses of Azetidine
The main uses of azetidine are in reagent products for research and development and organic synthesis materials. Azetidine can be synthesized with various protective groups on the nitrogen atom of the four-membered ring, which makes it a useful compound as a side chain for pharmaceuticals. Azetidine itself is not a frequently used compound, but its derivatives, azetidines, are used as pharmaceuticals.
Research on azetidine compounds as pharmaceuticals began in the late 1950s and is currently being conducted for use in rheumatoid arthritis, multiple sclerosis, osteoporosis, and osteolysis, and as agents for the prevention or treatment of cancer. Azetidine and its derivatives are not abundant in nature, but naturally occurring derivatives such as mugineic acid and azetidine-2-carboxylic acid exist.
Properties of Azetidine
Azetidine has a molecular weight of 57.09, a boiling point of 61-62°C, and a colorless to pale yellow liquid appearance at room temperature. It has a characteristic odor.
The flash point is -21°C in a sealed flash point test. It has a density of 0.847 g/mL and is miscible with water. It is more basic than most secondary amines, and the acid dissociation constant pKa of conjugated acids is 11.29.
The reason for this is thought to be that the carbon chain has a ring structure, and the lone pair of nitrogen atoms is not easily sterically hindered and sticks out. It is highly flammable and corrosive to the skin.
Types of Azetidine
Azetidine is a substance commonly sold as a reagent product for research and development. It is available in a variety of capacities, including 250 mg, 1 g, 5 g, and 25 g. Although it is offered in capacities that are easy to handle in the laboratory, it is a relatively expensive compound. It is usually a reagent product that is often stored under refrigeration.
Azetidine is also sold as a hydrochloride salt. Other derivatives include various compounds with substituents on the nitrogen atom, as well as compounds with substituents on the carbon atom, such as azetidine-2-carboxylic acid, azetidine-3-carboxylic acid, and azetidine-3-ol.
Other Information on Azetidine
1. Synthesis of Azetidine
Azetidine is synthesized by the reaction of 3-bromopropylamine with potassium hydroxide and the reduction of p-toluenesulfonylazetidine with metallic sodium. p-Toluenesulfonylazetidine is obtained from 1,3-dibromopropane and p-toluenesulfonamide.
2. Reactivity of Azetidine
Azetidine opens the ring when heated in dilute hydrochloric acid to form 3-chloropropylamine, 3-aminopropanol, and other compounds. It is usually stable in a suitable storage environment, but heat, flame, and sparks should be avoided. Hazardous mixtures are strong oxidizing agents and strong acids.
3. Azetidine Hazard and Regulatory Information
Azetidine is classified in the GHS classification as
- Inflammable liquid: Category 2
- Skin corrosiveness/irritation: Category 1B
- Serious eye damage/eye irritation: Category 1
When handling, avoid heat, flame, and sparks, and wear appropriate protective equipment such as protective gloves, protective clothing, protective glasses, and protective masks. By law, the product is designated as Class 4 Inflammable Liquid, Petroleum No. 1, Hazardous Class II, Non-water soluble liquid under the Fire Service Act.