2-Benzoxazolinone

2-Benzoxazolinone Basic information
Product Name:2-Benzoxazolinone
Synonyms:USAF ek-5429;usafek-5429;2,3-Dihydro-2-oxo-1,3-benzoxazole;Benzoxazolin-2-one, 1,3-Benzoxazol-2(3H)-one;2-Benzooazolinone;2-Benzoxazolinone,98%;BENZOXAZOLONE (2-BENZOXAZOLINONE);Benzoxazol-2(3H)-one
CAS:59-49-4
MF:C7H5NO2
MW:135.12
EINECS:200-430-0
Product Categories:Oxazole&Isoxazole
Mol File:59-49-4.mol
2-Benzoxazolinone Structure
2-Benzoxazolinone Chemical Properties
Melting point 137-139 °C(lit.)
Boiling point 248.79°C (rough estimate)
density 1.3124 (rough estimate)
refractive index 1.5800 (estimate)
Fp 160 °C
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Powder
pka9.50±0.70(Predicted)
color Light beige to brown-gray
Water Solubility soluble in hot water
BRN 119481
InChIKeyASSKVPFEZFQQNQ-UHFFFAOYSA-N
LogP1.160
CAS DataBase Reference59-49-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoxazolone(59-49-4)
EPA Substance Registry System2-Benzoxazolinone (59-49-4)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-22-24/25-36/37/38
Safety Statements 36-24/25-26
RIDADR 2811
WGK Germany 3
RTECS DM4905000
Hazard Note Harmful
TSCA Yes
HS Code 29349990
ToxicityLD50 orl-rat: 700 mg/kg MDCHAG 4(1),308,64
MSDS Information
ProviderLanguage
2,3-Dihydro-1,3-benzoxazol-2-oneEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
2-Benzoxazolinone Usage And Synthesis
Chemical Propertieslight beige to brown-grey powder. insoluble in water, soluble in benzene, chlorobenzene and other solvents.
Uses2-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.
Preparation2-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.
DefinitionChEBI: 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 Description2-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 Reactivity2-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 ProfilePoison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic fumes of NOx.
2-Benzoxazolinone Preparation Products And Raw materials
Raw materials2-Aminophenol–>S,S-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate–>1-Phenyltetrazole-5-thiol–>2,3-DICHLORO-5-NITROPYRIDINE–>Salicylhydroxamic acid–>3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
Preparation Products2,6-Dichlorobenzoxazole–>(2-OXO-1,3-BENZOXAZOL-3(2H)-YL)ACETALDEHYDE–>2(3H)-Benzoxazolone, 3-(3-hydroxypropyl)-–>3-(2-CHLORO-ACETYL)-3H-BENZOOXAZOL-2-ONE–>[3-(3-CHLORO-9-OXA-1,2,10-TRIAZA-ANTHRACEN-10-YL)-PROPYL]-DIMETHYL-AMINE–>2-Chloro-10-methyl-3,4-diazaphenoxazine–>2(3H)-Benzoxazolone, 5-hydroxy-

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