76751-94-5

Basic information

• Product Name: 6-[(4-chlorophenyl)carbonyl]-1,3-benzoxazol-2(3H)-one
• CAS NO: 76751-94-5
• Molecular Formula: C₁₄H₈ClNO₃
• Molecular Weight: 273.6712
• Mol File: 76751-94-5.mol
• Article Data: 7

Chemical Properties

• Density: 1.424g/cm³
• Refractive Index: 1.636
• CAS DataBase Reference: 6-[(4-chlorophenyl)carbonyl]-1,3-benzoxazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(4-chlorophenyl)carbonyl]-1,3-benzoxazol-2(3H)-one(76751-94-5)
• EPA Substance Registry System: 6-[(4-chlorophenyl)carbonyl]-1,3-benzoxazol-2(3H)-one(76751-94-5)

Safety Data

• Hazardous Substances Data: 76751-94-5(Hazardous Substances Data)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 59-49-4 2-Benzoxazolinone 
• 74-11-3 para-chlorobenzoic acid 
• 790-41-0 4-chlorobenzoic anhydride 
• 13787-58-1 3-(4-chlorobenzoyl)-3H-1,3-benzoxazol-2-one 

Downstream Products

• 76752-12-0 2-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid 
• 116337-64-5 7-(4-Chloro-benzoyl)-2-methyl-4H-benzo[1,4]oxazin-3-one 
• 116337-65-6 7-(4-Chloro-benzoyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one 
• 116337-63-4 7-(4-Chloro-benzoyl)-4H-benzo[1,4]oxazin-3-one 
• 76752-07-3 2-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid ethyl ester 
• 76751-97-8 [6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-acetic acid 
• 76752-02-8 3-[6-(4-Chloro-benzoyl)-2-oxo-benzooxazol-3-yl]-propionic acid 
• 123172-45-2 (4-Amino-3-hydroxy-phenyl)-(4-chloro-phenyl)-methanone 

Relevant articles and documents

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.

ACYLATION OF 2,3-DIHYDROBENZOXAZOL-2-ONE IN A TWO STEPS METHOD INVOLVING AN ACYL MIGRATION

A new method of acylation of 2,3-dihydrobenzoxazol-2-one 1 is proposed in a two-steps procedure involving an acyl migration.