7748-58-5

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-6-NITROBENZO(1,3)DIOXOLE is used as an intermediate in the synthesis of bis-indolone-N-oxides, which possess significant biological and pharmacological importance. These bis-indolone-N-oxides are known for their diverse range of biological activities, including potential applications in the development of new drugs for the treatment of various diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-BROMO-6-NITROBENZO(1,3)DIOXOLE serves as a valuable building block for the creation of more complex organic molecules. Its unique structural features, including the bromine and nitro groups, make it a versatile compound for use in various synthetic reactions, leading to the formation of a wide array of chemical products with different applications.

InChI:InChI=1/C7H4BrNO4/c8-4-1-6-7(13-3-12-6)2-5(4)9(10)11/h1-2H,3H2

Upstream product

• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 120-57-0 piperonal 

Downstream Products

• 68560-11-2 2-methylthio-4,5-methylenedioxynitrobenzene 
• 93415-73-7 N-(2'-Methyl-6'-nitrophenyl)-5-amino-6-nitro-1,3-benzdioxol 
• 93415-80-6 N-(4'-Carboethoxy-2'-nitrophenyl)-5-amino-6-nitro-1,3-benzdioxol 
• 859979-85-4 4-bromo-2-methoxy-5-nitro-phenol 
• 75437-91-1 5-Bromo-4-nitro-2-phenoxymethoxy-phenol 
• 75437-92-2 4-Nitro-5-phenoxy-2-phenoxymethoxy-phenol 
• 93399-40-7 N-(2'-Nitrophenyl)-5-amino-6-nitro-1,3-benzdioxol 
• 108902-88-1 1-(2-bromophenylthio)-4,5-methylenedioxy-2-nitrobenzene 
• 158719-77-8 5-(2-bromophenylthio)-2-(2-bromophenylthiomethoxy)-4-nitrophenol 
• 158719-71-2 4-nitro-5-phenylthio-2-phenylthiomethoxyphenol 
• 67851-24-5 2-(6-Nitro-benzo[1,3]dioxol-5-ylsulfanyl)-phenylamine 
• 158719-79-0 5-(2-Amino-phenylsulfanyl)-2-(2-amino-phenylsulfanylmethoxy)-4-nitro-phenol 
• 68560-13-4 6-(methylthio)benzo[d][1,3]dioxol-5-amine 
• 53984-22-8 (E)-5-nitro-6-styrylbenzo[d][1,3]dioxole 

Relevant academic research and scientific papers

HETEROCYCLIC LSF INHIBITORS AND THEIR USES

The present invention is directed to heterocyclic SV40 Factor (LSF) inhibitors and their uses. In some implementations, the present invention discloses small-molecule compounds of Formula (I). In some implementations, the compounds of Formula (I) are used

Synthesis and biological evaluation of new bis-indolone-N-oxides

A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They did not cause any haemolysis (300 μg mL-1). Of the synthesized bis-indolones, compound 1a had the most potent antiplasmodial activity (IC50 = 0.763 μmol L-1 on the FcB1 strain) with a selectivity index (CC50 MCF7/IC 50 FcB1) of 35.6. No potency against the tested microbial strains was observed.

Synthesis of the 3,4,5-trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for divergent preparation of cytotoxic biaryls

The regioselective synthesis of the 3,4,5-trimethoxy-2-(3,4-methylenedioxy- 6-nitrophenyl)benzaldehyde as key intermediate for divergent preparation of cytotoxic biaryl lignans was achieved in three steps from commercially available starting materials. Re

Stereoselective Synthesis of an Analogue of Podophyllotoxin by an Intramolecular Diels-Alder Reaction

The dihydrobenzocyclobutene 90 having a 4-hydroxycrotonate unit attached via an ester linkage as an internal dienophile can be cyclized to a 3:1 mixture of the trans lactone 92 (an analogue of podophyllotoxin, 1) and the cis lactone 93.This stereoselective reaction proceeds via the intermediacy of the o-quinodimethane 91 which cyclizes from the endo transition state 91n in preference to the exo-one 91x, presumably because of stabilization of the former by secondary orbital overlap.This result provides evidence that a proposed general route to the synthesis of podophyllotoxin, 1, and its analogues via the internal cycloaddition of the o-quinodimethane 8 to 9n may prove successful.Several possible approaches to the synthesis of the trans-2-aryldihydrobenzocyclobutenol 4 are described.The benzyne 11 was prepared and underwent but no cycloadditions.Although the 2-bromobenzocyclobutenone 23 could be synthesized in an efficient manner, it proved impossible to convert it into 4 by means of the aryl organometallic reagents 22ab.The bromo epoxide 52 was prepared and subjected to metal-halogen exchange and Lewis acid catalyzed epoxide rearrangement in an attempt to prepare 4.The aldehyde 56 was obtained in this reaction, clearly indicating that the desired intermediate 54 had been formed but could not be trapped under these conditions.Two ring contraction routes to 4 are also described, both beginning with the 1-indanone 74 prepared in good yield from piperonal 14.The diol monomesylate 78, prepared from 74, suffered base-catalyzed E2 elimination rather than the desired rearrangement to 80.The diazo ketone 83 underwent Wolff rearrangement to give the desired ester 84, but only in 7percent yield.Two interesting transformations were observed in these ring contraction schemes, namely the formation of the oxathiole dioxide 77 on mesylation of the ketol 75 and the preparation of the diazirene 86 on photolysis of the diazo ketone 83 at long wavelengths.The ester 84 was then saponified to the acid 87 which was coupled with methyl 4-hydroxycrotonate, 5, to give 90.The assignment of the structures of the products of thermolysis of 90 was based on high field 1H NMR and analogy to the spectra of similar compounds in the literature.