569-06-2

Basic information

• Product Name: 1-Fluoroanthraquinone
• Synonyms: 1-Fluoro-9,10-anthracenedione;1-Fluoro-9,10-anthraquinone;1-Fluoroanthraquinone
• CAS NO: 569-06-2
• Molecular Formula: C₁₄H₇FO₂
• Molecular Weight: 226.2026
• Mol File: 569-06-2.mol

Chemical Properties

• Boiling Point: 395.5°Cat760mmHg
• Flash Point: 150.7°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 1.83E-06mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 1-Fluoroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Fluoroanthraquinone(569-06-2)
• EPA Substance Registry System: 1-Fluoroanthraquinone(569-06-2)

Safety Data

• Hazardous Substances Data: 569-06-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H7FO2/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7H

Upstream product

• 82-37-1 9,10-dioxo-9,10-dihydroanthracene-1-diazonium hydrogen sulfate 
• 82-45-1 1-amino-9,10-anthracenedione 
• 361-19-3 1-fluoro-4-methyl-9,10-dihydroanthracene-9,10-dione 
• 625-98-9 3-chlorofluorobenzene 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 7651-80-1 1-fluoroanthracene 
• 361-20-6 4-fluoro-9,10-dioxo-9,10-dihydro-anthracene-1-carboxylic acid 
• 82-44-0 1-chloroanthracene-9,10-dione 

Downstream Products

• 84-65-1 9,10-phenanthrenequinone 
• 204513-96-2 1-Nitro-4-phenoxyanthraquinone 
• 43033-00-7 1,4-diphenoxyanthracene-9,10-dione 
• 75300-18-4 1,4-Di(phenylthio)anthraquinone 
• 54642-23-8 JNK Inhibitor II, Negative Control 
• 129-43-1 1-hydroxyanthraquinone 
• 82-38-2 1-(methylamino)anthraquinone 
• 5960-55-4 1-dimethylaminoanthraquinone 
• 117499-94-2 1-(N',N'-Dimethyl-hydrazino)-anthraquinone 
• 4465-58-1 1-(2-hydroxyethylamino)anthracene-9,10-dione 
• 7651-80-1 1-fluoroanthracene 
• 85683-71-2 9-(1,1-dimethyl-2-phenylethyl)-1-fluoro-9,10-dihydro-9-anthrol 
• 86709-70-8 1-<2-(Benzylideneamino)ethoxy>anthracene-9,10-dione 

Relevant articles and documents

Improved solid-state photomechanical materials by fluorine substitution of 9-anthracene carboxylic acid

Four fluorinated derivatives of 9-anthracene carboxylic acid (9AC), a molecule that shows a reversible photomechanical response in its crystal form, have been synthesized and characterized. The spectroscopic properties and crystal structures of 4-fluoro-9-anthracene carboxylic acid (4F-9AC), 2-fluoro-9-anthracene carboxylic acid (2F-9AC), 10-fluoro-9-anthracene carboxylic acid (10F-9AC), and 2,6-difluoro-9-anthracene carboxylic acid (2,6DF-9AC) are all very similar to those of 9AC. However, their photomechanical properties vary widely. 405 nm light was used to induce [4 + 4] photodimerization and a mechanical response in crystalline microneedles and ribbons. Both the photodimer dissociation rate and the mechanical recovery varied by more than an order of magnitude, with 4F-9AC exhibiting the most rapid recovery time, on the order of 30 s. Nanoindentation measurements show that this crystal has a slightly reduced elastic modulus and a significantly reduced hardness, making it less brittle than the 9AC crystal. Large 4F-9AC crystals remain intact after irradiation, without fragmenting, while microneedles can undergo more than 100 mechanical bending cycles. Given the similarity of the crystal packing in all five molecules, the improved photomechanical properties must arise from subtle changes in intermolecular interactions or possibly differences in disorder. These results demonstrate that it is possible to significantly improve the properties of photomechanical materials through small modifications of the molecular structure.

Efficient Synthesis of Alkoxyanthraquinones from Fluoroanthraquinones and Their Preliminary Electrochemistry

The reaction of 1,8-dichloroanthraquinone with CsF in DMSO under anhydrous conditions affords improved yields of the corresponding difluoro derivative 2.Nucleophilic displacement reactions using simple alkoxide nucleophiles or crown ether derivatives on 2 allows the preparation of 1,8-dialkoxyanthraquinones 5-10 in good to excellent yields.Compounds 8 and 10 exhibit enhanced sodium binding properties upon reduction to the corresponding mono- and dianions.Cation binding enhancements are larger than those previously observed for structurally related systems.

KINETICS AND MECHANISM OF DIELS-ALDER ADDITIONS OF TETRACYANOETHYLENE TO ANTHRACENE DERIVATIVES-III EFFECT OF SUBSTITUENTS ON RATES AND INTERMEDIATE COMPLEX FORMATION

In Diels-Alder additions of tetracyanoethylene to 1,2-, and 9-substituted anthracenes, formation constants (K) for the intermediate complexes have been separated from the global rate constant (K2obs).The relatively small range of values of K indicates a very small charge transfer in the complexes.The transition state for conversion of complex into adduct showed a marked degree of charge development, particularly for the 9-substituted derivatives (ρ=-7).Substituents in the outer rings gave good rate correlations with composite constants (?m+ + ?p+) with a ρ value of -3.The substituent effects are discussed in terms of these and other parameters.Values for equilibrium constants for the overall addition (Keq) are reported.

Synthesis of fluorine-substituted anthraquinones and azaanthraquinones

Using 1,4-dipolar-aryne cycloaddition methodology, a convenient, short synthesis of several fluoroanthraquinones is presented which involves the reaction of haloarenes and 3-cyanophthalides in the presence of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).The fluorine substituent(s) can be introduced by using fluorine-substituted haloarenes and/or 3-cyanophthalides.Similarly, fluorine-substituted pyridines can be prepared by treating fluorine-substituted cyanophthalides and halopyridines in the presence of lithium diisopropylamide.

Restricted Rotation Involving the Tetrahedral Carbon. XLV. Appearance of a Maximum in the Rotational Barriers of 9-(1,1-Dimethyl-2-phenylethyl)triptycenes at a Medium-sized peri-Substituent

Rotational isomers of seven peri-substituted 9-(1,1-dimethyl-2-phenylethyl)triptycene derivatives were stereoselectively synthesized and classical kinetics on rotational isomerization were studied.While compounds with relatively small peri-substituents (F