64460-57-7

Basic information

• Product Name: 5-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one
• Synonyms: 5-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one
• CAS NO: 64460-57-7
• Molecular Weight: 257.676
• Mol File: 64460-57-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one(64460-57-7)
• EPA Substance Registry System: 5-chloro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one(64460-57-7)

Safety Data

• Hazardous Substances Data: 64460-57-7(Hazardous Substances Data)

Upstream product

• 19407-43-3 2-benzoylamino-6-chloro-benzoic acid 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 98-88-4 benzoyl chloride 
• 56-93-9 benzyltrimethylammonium chloride 
• 107-06-2 1,2-dichloro-ethane 
• 75-44-5 phosgene 
• 95-50-1 1,2-dichloro-benzene 
• 49684-74-4 C₁₂H₉ClN₂O 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 495-18-1 Benzohydroxamic acid 

Relevant articles and documents

Rh(III)-Catalyzed C-H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

A highly efficient Rh(III)-catalyzed C-H diamidation and diamidation/intramolecular cyclization of N-iminopyridinium ylides with dioxazolones has been developed, providing diamidated products and benzoxazinone products in good to excellent yields. Notably, the tunable selectivity of this reaction can be controlled by simply switching the solvent and the temperature. This reaction features operational simplicity, a broad substrate scope, and a good functional group tolerance.

Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples

The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.