2-Benzoxazolinone

Chemical properties

light beige to brown-grey powder. insoluble in water, soluble in benzene, chlorobenzene and other solvents.

The Uses of 2-Benzoxazolinone

2-Benzoxazolinone is used in the study of the antioxidant activity of heterocyclic chalcones, screening of hydrazines as inhibitors of immune suppressive enzyme indoleamine dioxygenase 1, design and the development of the inhibitors of nitric oxide synthases.

Preparation

2-benzoxazolinone synthesis method: add o-aminophenol, urea and solvent chlorobenzene into the reaction kettle, protect with nitrogen, the reaction temperature is 50～132 ℃, the reaction time is 6h, after the reaction is completed, it is cooled with ice brine, crystallized, Filter the finished product. It is also possible to use o-aminophenol to react with phosgene in the solvent chlorobenzene, quickly pass phosgene within 20 ~ 40 ° C, then heat up to 100 ~ 130 ° C, and then pass phosgene at a lower speed, after the reaction is completed, pass nitrogen to catch up. Phosgene, after work-up, can also obtain 2-benzoxazolinone.

Definition

ChEBI: 2-benzoxazolinone is a member of the class of benzoxazoles that is 2,3-dihydro-1,3-benzoxazole carrying an oxo group at position 2. It has a role as an allelochemical and a phytoalexin.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 6, p. 123, 1969 DOI: 10.1002/jhet.5570060124
Synthetic Communications, 34, p. 735, 2004 DOI: 10.1081/SCC-120027722
Synthesis, p. 1032, 1983 DOI: 10.1055/s-1983-30616

General Description

2-Benzoxazolinone is a phytoanticipin and its biotransformation by endophytic fungi isolated from Aphelandra tetragona was studied. 2-Benzoxazolinone is a natural chemical produced by rye (Secale cereale) and has strong phytotoxic properties.

Chemical Reactivity

2-benzazolinone is chemically active. in its molecular structure, the hydrogen atom at the 3-position can undergo a methylolation reaction with formaldehyde, and the hydrogen at the 6-position of the benzene ring is easily replaced by chlorine. it is easy to open ring to generate 2-hydroxyphenylamino acid in strong alkaline medium.

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic fumes of NOx.