123040-50-6

Basic information

• Product Name: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE
• Synonyms: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE
• CAS NO: 123040-50-6
• Molecular Formula: C₁₀H₇Cl₂NO₃
• Molecular Weight: 260.07348
• Mol File: 123040-50-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(123040-50-6)
• EPA Substance Registry System: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(123040-50-6)

Safety Data

• Hazardous Substances Data: 123040-50-6(Hazardous Substances Data)

Usage

Chemical compound

6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE

Classification

benzoxazoles

Substitutions

6-chloro on the benzene ring, acyl chloride functional group at the 8-position

Reactivity

highly reactive

Uses

intermediates in organic synthesis, formation of amides, esters, pharmaceuticals, agrochemicals, fine chemicals

Upstream product

• 141761-83-3 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester 
• 5043-79-8 5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester 
• 123040-75-5 methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate 
• 5043-81-2 3-amino-5-chloro-2-hydroxybenzoic acid methyl ester 
• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 123040-79-9 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid 

Downstream Products

• 123040-16-4 Azasetron hydrochloride 
• 123040-69-7 azasetron 

Relevant articles and documents

Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides

Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).