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General Description

Phenoxazine (C12H9NO) is a heterocyclic compound whose structure consists of an oxazine bonded to 2 benzene rings. It forms the nucleus of a wide variety of pharmaceutical molecules and dye-stuffs. It is a grey to off-white powder with a purity of 98% that acts as a transitional agent for 4,6-bis(diphenylphosphino)phenazine, and it can also be applied as a transitional agent for catalysts, pharmaceuticals, and oled.

Properties

Phenoxazine has a molecular weight of 183.21 g/mol and a monoisotopic mass of 183.068 g/mol, which is also its exact mass. The compound has a heavy atom count of 14 and a complexity of 187. Phenoxazine has a melting point of 1560 C and it dissolves in water at the rate of 2.130 mg/l at 250 C

Uses

Phenoxazine and its derivatives are not widely used hence the oxazine dyes are the only commercially viable derivatives. Certain oxazine dyes such as Nile blue dye is used in the preferential staining of brain cancer tissue since some of these dyes can inhibit the growth of these tumors. Various studies have explored the methods of preparation of boronic acids in a way that can result in a boron derivative of Phenoxazine (Nile blue dyes) which can be beneficial in cancer chemotherapy.

Preparation

The preparation of Phenoxazine and its by-products revolves around cyclization reactions. Each reaction is distinct from the other based on the starting materials and the conditions applied to the preparation process. Most cyclization reactions involved in the production of Phenoxazine and its by-products take place through one crucial step reactions as opposed to a series of steps where an aryl ether or an aryl amine would be obtained.

Hazards

The toxicological effects of Phenoxazine have not been investigated thoroughly but exposure to the compound may harm the eyes, skin, digestive tract and respiratory tract through irritation.

Chemical Properties

grey to green-grey fine crystalline powder

Purification Methods

Crystallise phenoxazine from EtOH and sublime it in vacuo. If too impure then extract it in a Soxhlet extractor using toluene. Evaporate the solvent and dissolve the residue (ca 100g) in *C6H6 (1L), CARCINOGEN (use an efficient fume cupboard) and chromatograph it through an Al2O3 column (50 x 450 mm) using *C6H6. The eluent (ca 3L) is evaporated to ca 150mL and cooled when ca 103g of phenoxazine m 149-153o is obtained. Sublimation yields platelets m 158-159o. It forms a green picrate m 141.5-142o. [Gilman & Moore J Am Chem Soc 79 3485 1957, Müller et al. J Org Chem 24 37 1959, Beilstein 27 I 223, 27 III/IV 1209.]