2285-06-5

Basic information

• Product Name: Diazene, bis(pentafluorophenyl)-
• Synonyms: Diazene, bis(pentafluorophenyl)-;Decafluoroazobenzene
• CAS NO: 2285-06-5
• Molecular Formula: C₁₂F₁₀N₂
• Molecular Weight: 362.1258
• Mol File: 2285-06-5.mol

Chemical Properties

• Boiling Point: 353.5 °C at 760 mmHg
• Flash Point: 167.6 °C
• Appearance: /
• Density: 1.74 g/cm³
• Vapor Pressure: 7.27E-05mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: Diazene, bis(pentafluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(pentafluorophenyl)-(2285-06-5)
• EPA Substance Registry System: Diazene, bis(pentafluorophenyl)-(2285-06-5)

Safety Data

• Hazardous Substances Data: 2285-06-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12F10N2/c13-1-3(15)7(19)11(8(20)4(1)16)23-24-12-9(21)5(17)2(14)6(18)10(12)22/b24-23+

Upstream product

• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 15855-26-2 phenylsulfonyliminoselenium dichloride 
• 287-92-3 Cyclopentane 
• 1423-15-0 perfluorophenyl azide 
• 58749-38-5 N,N-dichloropentafluoroaniline 
• 73750-54-6 Se,Se-dichloro-N-pentafluorobenzoylselenoimine 
• 73750-52-4 Se,Se-dichloro-N-pentafluorophenylsulphonylselenoimine 
• 828-73-9 pentafluorophenyl hydrazine 
• 546-67-8 lead(IV) tetraacetate 
• 69642-11-1 cis-1,2-bis(perfluorophenyl)diazene 
• 106-97-8 n-butane 
• 1800-29-9 decafluoroazoxybenzene 
• 36375-78-7 pentafluorophenyl nitrene 
• 108-88-3 toluene 

Downstream Products

• 129492-96-2 2C₁₆H₃₆N⁽¹⁺⁾*C₁₂F₈N₂O₂^(2-) 
• 25593-03-7 4-hydroxynonafluoroazobenzene 
• 129520-55-4 2-hydroxynonafluoroazobenzene 
• 69642-11-1 cis-1,2-bis(perfluorophenyl)diazene 
• 1800-29-9 decafluoroazoxybenzene 
• 25593-01-5 4,4'-C₂H₅O-C₆F₄NNC₆F₄-OC₂H₅ 
• 25593-05-9 4,4'-C₆H₅S-C₆F₄NNC₆F₄-SC₆H₅ 
• 2010-66-4 4-CH₃O-C₆F₄NNC₆F₅ 
• 2010-67-5 4,4'-dimethoxyoctafluoroazobenzene 
• 2010-73-3 4,4'-HC₆F₄NHNHC₆F₄H 
• 2010-69-7 2,2',4,4'-Tetramethoxy-3,5,6,3',5',6'-hexafluor-azobenzol 
• 2787-85-1 4,4'-CH₃O-C₆F₄N(O)NC₆F₄OCH₃ 
• 2379-19-3 N,N'-bis(pentafluorophenyl)-hydrazine 

Relevant articles and documents

Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes

A high ortho regioselectivity in nucleophilic aromatic substitution in low polar solvents is reported in the reaction of polyfluorinated azobenzenes with anilines. o-Anilino substituted derivatives could be easily transformed into non-symmetric phenazines

Switching the Spin State of Pentafluorophenylnitrene: Isolation of a Singlet Arylnitrene Complex

The chemistry of arylnitrenes is dominated by their triplet ground states and excited open-shell singlet states. This results in radical-type reactions and unwanted rearrangements, which diminish the use of arylnitrenes as intermediates in organic synthes

Mechanochemical oxidation of fluorinated anilines to symmetric azobenzenes

A solventless mechanochemical methodology for the oxidation of electron-poor fluorinated anilines to the corresponding symmetrical azo compounds has been developed. In this process phenyliodine(III)diacetate and inexpensive calcium hypochlorite demonstrat

Metal-Organic Frameworks as Hosts for Fluorinated Azobenzenes: A Path towards Quantitative Photoswitching with Visible Light

Fifteen new photochromic hybrid materials were synthesized by gas phase loading of fluorinated azobenzenes, namely ortho-tetrafluoroazobenzene (tF-AZB), 4H,4H′-octafluoroazobenzene (oF-AZB), and perfluoroazobenzene (pF-AZB), into the pores of the well-known metal-organic frameworks MOF-5, MIL-53(Al), MIL-53(Ga), MIL-68(Ga), and MIL-68(In). Their composition was analysed by elemental (CHNS) and DSC/TGA. For pF-AZB0.34@MIL-53(Al), a structural model based on high-resolution synchrotron powder diffraction data was developed and the host-guest and guest-guest interactions were elucidated from this model. These interactions of O?H???F and π???π type were confirmed by significant shifts of the O?H frequencies in loaded and unloaded MOFs of the MIL-53 and MIL-68 series. Most remarkably, all of the synthesized F-AZB@MOF systems can be switched with visible light, and some of them show almost quantitative (>95 %) photo-isomerization between its E and Z forms with no significant fatigue after repeated switching cycles.

Synthesis of Azobenzenes Using N-Chlorosuccinimide and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)

A convenient method for the synthesis of symmetrical azobenzenes is reported. This one-step procedure involves treatment of anilines with N-chlorosuccinimide (NCS) and organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). A wide range of commercially available substituted anilines readily participate in this reaction to produce the corresponding azobenzenes in moderate-to-excellent yields in minutes.

Electrocatalytic Z → E Isomerization of Azobenzenes

A variety of azobenzenes were synthesized to study the behavior of their E and Z isomers upon electrochemical reduction. Our results show that the radical anion of the Z isomer is able to rapidly isomerize to the corresponding E configured counterpart with a dramatically enhanced rate as compared to the neutral species. Due to a subsequent electron transfer from the formed E radical anion to the neutral Z starting material the overall transformation is catalytic in electrons; i.e., a substoichiometric amount of reduced species can isomerize the entire mixture. This pathway greatly increases the efficiency of (photo) switching while also allowing one to reach photostationary state compositions that are not restricted to the spectral separation of the individual azobenzene isomers and their quantum yields. In addition, activating this radical isomerization pathway with photoelectron transfer agents allows us to override the intrinsic properties of an azobenzene species by triggering the reverse isomerization direction (Z → E) by the same wavelength of light, which normally triggers E → Z isomerization. The behavior we report appears to be general, implying that the metastable isomer of a photoswitch can be isomerized to the more stable one catalytically upon reduction, permitting the optimization of azobenzene switching in new as well as indirect ways.

Azo?phenyl stacking: A persistent self-assembly motif guides the assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals

We describe a novel, persistent motif of molecular assembly in photo-mechanical crystals and cocrystals of fluorinated cis-azobenzenes. The azo?phenyl stacking, preserved upon either chemical substitution or halogen-bonded cocrystallization, guides the assembly of fluorinated cis-azobenzenes into columnar stacks and drives the formation of crystals with needle-like morphologies optimal for photo-mechanical motion.

Ortho-Fluoroazobenzenes: Visible Light Switches with Very Long-Lived Z Isomers

Improving the photochemical properties of molecular photoswitches is crucial for the development of light-responsive systems in materials and life sciences. ortho-Fluoroazobenzenes are a new class of rationally designed photochromic azo compounds with opt

Formation of polyfluorinated azobenzenes and azophenols in the reactions of chloropentafluoro-cyclohexa-2,5- and -2,4-dienones with phenyl- and pentafluorophenylhydrazines

4-Chloropentafluorocyclohexa-2,5-dienone reacted with phenyl- and pentafluorophenylhydrazines in the presence of AlCl3 via addition to the carbonyl group with formation of the corresponding azobenzenes. The reaction of 6-chloropentafluorocycloh

A practical synthesis of azobenzenes through oxidative dimerization of aromatic amines using tert-butyl hypoiodite

A straightforward, convenient, and efficient synthetic method of azobenzenes through oxidative dimerization of aromatic amines using a unique and cost-effective iodinating reagent is described. This new method allows for easy access to both of symmetrical and unsymmetrical azobenzenes under extremely mild conditions. Georg Thieme Verlag Stuttgart. New York.