1691-65-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 3793, 1975 DOI: 10.1021/jo00913a044

InChI:InChI=1/C16H9F/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9H

Upstream product

• 129-00-0 pyrene 
• 137172-07-7 8,16-difluoro<2.2>metacyclophane-1,9-diene 
• 106892-39-1 cis-difluorodihydropyrene 
• 1606-67-3 1-aminopyrene 

Downstream Products

• 34246-96-3 1-methoxypyrene 
• 163631-86-5 N⁶-(1-nitropyren-8-yl)-3'-O-(tetrahydrofuranyl)-5'-O-trityldeoxyadenosine 
• 163631-85-4 N⁶-(1-nitropyren-6-yl)-3'-O-(tetrahydrofuranyl)-5'-O-trityldeoxyadenosine 

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Monofluorinated polycyclic aromatic hydrocarbons (F-PAHs) are useful reference compounds for a broad spectrum of PAH studies. The pyrene metabolite 1-hydroxypyrene is often used as a biomarker of PAH exposure. Two species, isopod (Porcellio scaber) and flatfish (Platichthys flesus), that produce...detailed

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Relevant academic research and scientific papers

ROOM TEMPERATURE FLUORINATION OF AROMATIC MOLECULES WITH CESIUM FLUOROXYSULPHATE

Room-temperature fluorination of benzene with cesium fluoroxysulphate in the presence of boron trifluoride as catalyst resulted in the formation of fluorobenzene, while reaction with naphthalene gave 1-fluoro and 2-fluoronaphthalene in the ratio 5:1, the overall yield being between 38 and 42percent.The fluorination of phenanthrene and pyrene should be carried out at higher dilution and needs no catalyst.Phenanthrene gave 9-fluorophenanthrene and 9,9-difluoro-10-keto-9,10-dihydrophenanthrene in the ratio 1:6 in a yield of about 70percent, while pyrene gave 1-fluoro and 4-fluoropyrene in the ratio 7.5:1.

ON THE RELATIVE SIZES OF HYDROGEN AND FLUORINE AS SUBSTITUENTS. TWO PATHWAYS FOR THE ISOMERIZATION OF SYN- TO ANTI-METACYCLOPHANES. THE SYNTHESIS OF THE FIRST DIHYDROPYRENE WITH INTERNAL FLUORINE SUBSTITUENTS.

The previously claimed syn-8,16-difluorometacyclophane 4 and metacyclophane-1,9-diene 18 were shown to be anti-isomers.The authentic syn-isomers were obtained by complexation of the arene rings of the precursor cyclophanes with a chromium tricarbonyl group, which enables pure syn-isomers to be separated and transformed to products.The isomerization of the syn-difluoro isomer 4 to the anti-isomer 5 occurs at much higher temperatures (300 grad C) than would be expected on the basis of the analogous methyl 3 (196 grad C) or hydrogen (0 grad C) compounds.Analysis of the bridge-SMe substituted examples, clearly indicates that bridge cleavage must occur in the isomerization of 4, while not in the case of 1, and thus two different pathways are operative depending on the internal substituents.The syn-diene 18 on warming valence isomerizes to the bridged annulene, the difluorodihydropyrene 19, the first example with internal substituents other than alkyl or aryl.

Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water

Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.

Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent

Reactions of N-fluorobis(phenylsulfonyl)amine with naphthalene, 1-methylnaphthalene, phenanthrene, anthracene, and pyrene without solvent were investigated. Sometimes the fluorination of aromatic compounds with N-fluorobis(phenylsulfonyl)amine without solvent proceeded more selectively than at the use of fluorinating reagents in solution.

Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation

The synthetic utility of N-fluoro-2,4-dinitro-imidazole NF-2,4-DNT, a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro-and tetrahydro-pyrene; benzo[a]anthracene; benzo[a]-and benzo[e] pyrene; perylene; 2,7-di-tert-butylphenanthrene;chrysene; 9-imethylanthracene and anthracene, as well as trans-15:16-dimethyl-dihydropyrene: azulene[2-a]lacenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH → NH2-PAH → N2+-PAH → F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using: other fluorinating agents.

Selective and efficient direct fluorination of polycyclic aromatic hydrocarbons using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

A new N-F fluorinating reagent 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor NFTh) was effectively used for selective fluorination of polycyclic aromatics. Naphthalene was site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene. In a series of substituted naphthalenes the regioselectivity and effectiveness of fluorination depended on the position and the nature of the substituents.

Synthesis of N-(1-nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides

A new type of 1-nitropyrene-DNA adduct via addition-elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O- protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 °C afforded N- (1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene- DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene-DNA adducts in vivo.