22906-23-6

Basic information

• Product Name: 1,2-di(9-phenanthryl)ethane
• Synonyms: 1,2-di(9-phenanthryl)ethane
• CAS NO: 22906-23-6
• Molecular Weight: 382.505
• Mol File: 22906-23-6.mol

Chemical Properties

• CAS DataBase Reference: 1,2-di(9-phenanthryl)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-di(9-phenanthryl)ethane(22906-23-6)
• EPA Substance Registry System: 1,2-di(9-phenanthryl)ethane(22906-23-6)

Safety Data

• Hazardous Substances Data: 22906-23-6(Hazardous Substances Data)

Upstream product

• 64-19-7 acetic acid 
• 169556-11-0 4-(N-methylanilino) 9-phenanthrylmethyl ether 
• 169556-06-3 5-anilinopentyl 9-phenanthrylmethyl ether 
• 169556-04-1 4-anilinobutyl 9-phenanthrylmethyl ether 
• 63561-88-6 9-((N,N-dimethylamino)methyl)phenanthrene 

Relevant articles and documents

Solvent-Dependent Behavior of Phenanthrene-Amine Intramolecular Exciplexes

The solvent dependence of the photophysical and photochemical behavior of several ((N,N-dimethylamino)-alkylphenanthrenes in which the amino group is attached to the phenanthrene at C9 or C1 via a short polymethylene chain has been investigated.Intramolecular exciplex fluorescence is observed in moderately polar solvents but not in nonpolar solvents.The solvent dependence of exciplex fluorescence is attributed to exergonic formation of solvated exciplexes with loose geometries in polar solvents and endergonic exciplex formation in nonpolar solvents.In the case of the (aminoethyl)phenanthrene exciplex fluorescence is observed in highly polar solvents, including dimethylformamide, dimethyl sulfoxide, and acetonitrile-water binary mixtures and in frozen polar glasses.In the case of the (aminomethyl)phenanthrene moderately efficient photodeamination to yield 9-methylphenanthrene and 1,2-di-9-phenanthrylethane is observed.The solvent and temperature dependence of the kinetics of exciplex formation and decay are discussed and compared to results for other intramolecular arene-amine exciplexes.

Carbon-Nitrogen Bond Cleavage of N-Alkyl-N-(9-phenanthrylmethyl)amines on Irradiation with Pyrex-filtered Light

In the presence of N-methylaniline, N-(9-phenanthrylmethyl)-N-alkylamines {alkyl = [CH2l3Ph, CH(CH2Ph)CO2Me, CH2CO2Me} undergo photolytic cleavage of the CH2-N bond to give substituted N-methylanilines.

Photocleavage of the C-O bond of 9-phenanthrylmethyl ω-anilinoalkyl ethers via photo-induced intramolecular electron transfer

Photoreactions of the title compounds nNHPh: Ar = 9-phenanthryl> 1 and 2 (n = 4 and 5) gave ω-alkan-1-ols 7 and 8 and ω-alkan-1-ols 9 and 10, respectively, by the cleavage of the C-O bond, while that of another title compound 3 (n = 6) gave spiro-compounds 17 and 18 with 12- and 14-membered-rings, respectively, as main products.The photoreaction is proposed to proceed via photo-induced intramolecular electron transfer from comparison of the reaction products with those in the photoreaction of ArCH2O3Ph 5 in the presence of N-methylaniline and acetic acid.The structures of spiro-compounds 17, 18, and the acetate of 9 were confirmed by X-ray crystal structure analysis.

Approaches to 1H-Cyclopropaphenanthrenes. Eliminations with 1a,9b-Dihydro-1H-cyclopropaphenanthrene Derivatives

Base-induced elimination of the sulfonium salt 2i in the presence of furan affords the addition products 7 and 8, derived from 1H-cyclopropaphenathrene (1) and the isomeric cyclopropene 5a (Scheme 3).Upon oxidation, the selenide 2c yields phenanthrene-9-methanol (9), presumably via 1.No evidence for the intermediate 1 is obtained from sulfoxide pyrolysis with 2e, which leads to products formed by radical pathways (Scheme 5).Reductive elimination of the disulfone 3b gives half-reduction to monosulfone 2g and complete reduction to cyclopropane 2 as well as 9-methylphenanthrene (15), but no evidence for the intermediate 1.