110704-42-2

Basic information

• Product Name: 3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE
• Synonyms: AKOS BB-7043;3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE
• CAS NO: 110704-42-2
• Molecular Formula: C₉H₆BrClN₂O
• Molecular Weight: 273.51
• Mol File: 110704-42-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 63-65°
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE(110704-42-2)
• EPA Substance Registry System: 3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE(110704-42-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 110704-42-2(Hazardous Substances Data)

Usage

General Description

3-(4-Bromophenyl)-5-(chloromethyl)-1,2,4-oxadiazole is a chemical compound with the molecular formula C9H7BrClN2O. It is a heterocyclic compound that contains both nitrogen and oxygen in its structure. 3-(4-BROMOPHENYL)-5-(CHLOROMETHYL)-1,2,4-OXADIAZOLE is often used in pharmaceutical research and drug development due to its potential biological activities. It has been studied for its potential use as an anticancer and antifungal agent. Additionally, it has been investigated for its antimicrobial and anti-inflammatory properties. Its unique structure and potential biological activities make it an important chemical compound for further research and development in the pharmaceutical industry.

Upstream product

• 19227-14-6 p-bromobenzamidoxime 
• 79-04-9 chloroacetyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 19227-14-6 (Z)-4-bromo-N′-hydroxybenzimidamide 
• 111457-50-2 C₉H₈BrClN₂O₂ 

Downstream Products

• 1357616-85-3 5-(azidomethyl)-3-(4-bromophenyl)-1,2,4-oxadiazole 
• 110722-44-6 {3-[3-(4-Bromo-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid 
• 138129-02-9 {3-[3-(4-Bromo-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid methyl ester 

Relevant articles and documents

Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties

Abstract: A tetraazacrown ether,4,9-di(prop-2-yn-1-yl)-1,4,9,12-tetraazacyclohexadecane-2,11-dione, bearingpropargyl groups on two nitrogens was synthesized starting from1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloadditionreactio

Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsulfonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (1H, 13C, 2D), mass spectra, and physical characteristics (mp and Rfvalues). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

Potent, orally active aldose reductase inhibitors related to zopolrestat: Surrogates for benzothiazole side chain

A broad structure-activity program was undertaken in search of effective surrogates for the key benzothiazole side chain of the potent aldose reductase inhibitor, zopolrestat (1). A structure-driven approach was pursued, which spanned exploration of three areas: (1) 5/6 fused heterocycles such as benzoxazole, benzothiophene, benzofuran, and imidazopyridine; (2) 5- membered heterocycles, including oxadiazole, oxazole, thiazole, and thiadiazole, with pendant aryl groups, and (3) thioanilide as a formal equivalent of benzothiazole. Several benzoxazole- and 1,2,4-oxadiazole- derived analogues were found to be potent inhibitors of aldose reductase from human placenta and were orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications. 3,4-Dihydro-4- oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1-phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10-9 M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg. Compound 139, 3,4-dihydro-4-oxo-3-[[(2-fluorophenyl)-1,2,4- oxadiazol-5-yl]methyl]-1-phthalazineacetic acid, with IC50 -8 M, caused a 69% reduction in sorbitol accumulation in rat sciatic nerve at an oral dose of 25 mg/kg. The thioanilide side chain featured in 3-[2-[[3- (trifluoromethyl)phenyl]amino]-2-thioxoethyl]-3,4-dihydro-4-oxo-1- phthalazineacetic acid (195) proved to be an effective surrogate for benzothiazole. Compound 195 was highly potent in vitro (IC50 = 5.2 x 10-8 M) but did not show oral activity when tested at 100 mg/kg. Additional structure-activity relationships encompassing a variety of heterocyclic side chains are discussed.