1545-69-3

Basic information

• Product Name: 9,10-Difluoroanthracene
• Synonyms: 9,10-Difluoroanthracene
• CAS NO: 1545-69-3
• Molecular Formula: C₁₄H₈F₂
• Molecular Weight: 0
• Mol File: 1545-69-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9,10-Difluoroanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Difluoroanthracene(1545-69-3)
• EPA Substance Registry System: 9,10-Difluoroanthracene(1545-69-3)

Safety Data

• Hazardous Substances Data: 1545-69-3(Hazardous Substances Data)

Upstream product

• 1494-21-9 9,10-difluoro-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-diepoxido-anthracene 
• 120-12-7 anthracene 
• 327-51-5 1,4-dibromo-2,5-difluorobenzene 
• 1766-96-7 9,10-difluoro-1,4,5,8-tetrahydro-1,4;5,8-diepoxido-anthracene 
• 13387-47-8 9,10-di-tert-butyl-9,10-dihydroanthracene 
• 58325-12-5 9,10-Difluor-1,2,3,4,5,6,7,8-octahydroanthracen 
• 523-27-3 9,10-Dibromoanthracene 

Downstream Products

• 84-65-1 9,10-phenanthrenequinone 
• 107817-07-2 C₂₈H₁₆F₄ 

Relevant articles and documents

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.

Structural Effects Controlling the Rate of the Retro-Diels-Alder Reaction in Anthracene Cycloadducts

We have undertaken a fairly broad study of how the structure of an anthracene cycloadduct affects the rate of its cycloreversion reaction.Based on the rate constants for retro-Diels-Alder (rDA) reactions of a variety of anthracene-type adducts conducted in diphenyl ether, we draw the following conclusions.The rDA reaction of anthracene cycloadducts is influenced by diene substituents in the following ways: (1) electron-donating groups increase the reaction rate, and the accelerating effect is subject to geometric modulation for a conjugating substituent like dimethylamino; (2) electron-withdrawing groups may decrease or increase the reaction rate , although the effect is rarely large; and (3) steric acceleration is relatively small and demonstrates an unprecedented bell-shaped structure-reactivity profile.Peripheral substitution of the adduct with siloxy groups results in a significant acceleration, even though the groups are three bonds removed from the reaction site.The same reaction is influenced by dienophile substituents in the following ways: (1) electron-withdrawing groups increase the rate of the reaction; (2) strongly conjugating substituents make the reaction much faster than predicted by classical electron-withdrawing or -donating ability due to a change to polar mechanism; and (3) there is no observable steric effect.