33953-73-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 1446, 1974 DOI: 10.1021/jo00926a035

Safety Profile

Questionable carcinogen withexperimental neoplastigenic and tumorigenic data.Mutation data reported. When heated to decomposition itemits acrid smoke and fumes.

InChI:InChI=1/C19H14O4S/c1-12-14-7-4-5-9-16(14)19(23-24(20,21)22)17-11-10-13-6-2-3-8-15(13)18(12)17/h2-7,9-11H,1,8H2,(H,20,21,22)

Upstream product

• 57984-09-5 phenaleno<1,9-bc>furan 
• 583-53-9 2,3-dibromobenzene 
• 120749-81-7 2,2a,3,4-tetrahydrophenaleno<1,9-bc>furan-4-ol 
• 120749-82-8 3,4-dihydrophenaleno<1,9-bc>furan-4-ol 
• 120749-80-6 4-oxo-2,2a,3,4-tetrahydrophenaleno<1,9-bc>furan 
• 63041-90-7 6-nitrobenzo(a)pyrene 
• 59417-86-6 6-fluorobenzopyrene 
• 693-03-8 n-butyl magnesium bromide 
• 53555-67-2 benzopyren-6-yl acetate 

Downstream Products

• 114617-55-9 benzoic acid benzo[def]chrysen-6-yl ester 
• 53555-67-2 benzopyren-6-yl acetate 

Relevant academic research and scientific papers

EPR and ENDOR Studies of 6-Substituted Benzopyrene Cation Radicals

The EPR spectrum of 6-methylbenzopyrene (6-CH3-BaP) in thallium(III)tris(trifluoroacetate)-trifluoroacetic acid (TTFA/TFA) solutions has been analyzed in terms of the 6-CH3-BaP cation radical with the aid of the ENDOR spectrum.Benzopyren (BaP) in TTFA/TFA gives an EPR and ENDOR spectra which are assigned and analyzed as the 6-(trifluoroacetoxy)benzopyrene cation radical.The EPR of several other 6-substituted BaP's have been investigated in both H2SO4 and TTFA/TFA solutions.Reactions of 6-CH3-BaP and 6-F-BaP in H2SO4 were observed.The EPR spectrum of 6-CH3-BaP(+.) changes over a period of an hour into the spectrum identical with that of 6-CH2OH-BaP(+.).Similarly, the EPR spectrum of 6-F-BaP(+.) in H2SO4 changes to one identical with 6-OH-BaP(+.).These observations are discussed in terms of their possible significance to the metabolic reactions of these compounds.

Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene

Photolabile 6-nitrobenzo[a]pyrene (6-nitroBaP) released nitric oxide (NO) under visible-light irradiation. The generation of NO and the concomitant formation of the 6-oxyBaP radical were confirmed by ESR. BaP quinones were also detected as further oxidize

PREPARATION, PROPERTIES, AND SOME CHEMICAL REACTIONS OF PHENALENOFURAN

The synthesis of hitherto unknown phenalenofuran (1), in 11 percent overall yield from 2-naphthol, has been achieved.Its (1)H and (13)C n.m.r. spectra have been fully assigned by means of heteronuclear 2D correlations.The furanoid moiety of (1) displays Diels-Alder diene reactivity in its reactions with benzyne, dimethyl acetylenedicarboxylate, and singlet oxygen.The furan ring of (1) also suffers oxidation by m-chloroperbenzoic acid and undergoes catalytic hydrogenation.This chemistry appears to be more characteristic of naphthofuran than of naphthofuran although both structural units co-exist in structure (1).