6931-31-3

Basic information

• Product Name: 2-Phenyl-1H-phenanthro[9,10-d]imidazole
• Synonyms: 2-Phenyl-1H-phenanthro[9,10-d]imidazole
• CAS NO: 6931-31-3
• Molecular Formula: C₂₁H₁₄N₂
• Molecular Weight: 294.35
• Mol File: 6931-31-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: 314 °C
• Boiling Point: 574.5±33.0 °C(Predicted)
• Appearance: /
• Density: 1.287±0.06 g/cm3(Predicted)
• PKA: 12.80±0.30(Predicted)
• CAS DataBase Reference: 2-Phenyl-1H-phenanthro[9,10-d]imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1H-phenanthro[9,10-d]imidazole(6931-31-3)
• EPA Substance Registry System: 2-Phenyl-1H-phenanthro[9,10-d]imidazole(6931-31-3)

Safety Data

• Hazardous Substances Data: 6931-31-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 771, 1946 DOI: 10.1021/ja01209a021

Upstream product

• 631-61-8 ammonium acetate 
• 100-52-7 benzaldehyde 
• 84-11-7 9,10-phenanthrenequinone 
• 484-47-9 lophine 
• 24108-44-9 3,5,6-triphenyl-[1,2,4]triazine 
• 133406-37-8 3,5,6-triphenyl-2,5-dihydro-1,2,4-triazin-4-ium chloride 
• 133406-38-9 3,5,6-triphenyl-2,5-dihydro-1,2,4-triazin-4-ium bromide 
• 133406-39-0 3,5,6-triphenyl-2,5-dihydro-1,2,4-triazin-4-ium hydrogen sulfate 
• 133406-37-8 3,5,6-triphenyl-2⁽⁴⁾,5-dihydro-triazinium chloride 
• 133406-40-3 2-methyl-3,5,6-triphenyl-2,5-dihydro-1,2,4-triazinium chloride 
• 2227-79-4 benzenecarbothioamide 
• 1670-14-0 benzamidine monohydrochloride 
• 85-01-8 phenanthrene 
• 134-81-6 benzil 

Downstream Products

• 1602990-88-4 6-methyl-5-phenylphenanthro[9',10':4,5]imidazo[2,1-a]isoquinoline 
• 1602990-90-8 5-methylene-6-phenyl-5,6-dihydrophenanthro[9',10':4,5]-imidazo[2,1-a]isoquinoline 
• 1602990-87-3 5,6-bis(4-chlorophenyl)phenanthro[9',10':4,5]imidazo[2,1-a]isoquinoline 
• 1602990-84-0 5,6-bis(4-methoxyphenyl)phenanthro[9',10':4,5]imidazo[2,1-a]isoquinoline 
• 58484-95-0 1-methyl-2-ohenyl-1H-phenanthro<9,10-d>imidazole 
• 112866-71-4 2-cyclohexyl-4,5,6,7,8,9,10,11-octahydro-1H-phenanthro[9,10-d]imidazole 
• 58484-86-9 2,2'-diphenyl-2'H-[1,2']bi[phenanthro[9,10-d]imidazolyl] 

Relevant articles and documents

Fluorescent phenanthroimidazoles functionalized with heterocyclic spacers: Synthesis, optical chemosensory ability and two-photon absorption (TPA) properties

Three series of fluorescent phenanthroimidazoles bearing heterocyclic spacers were synthesized in moderate to excellent yields and evaluated as optical chemosensors for ions as well as two-photon absorbing chromophores. Interaction of compounds 5-7 with anions and cations in acetonitrile and acetonitrile/H2O (95:5) showed them to be selective receptors for several anions (AcO-, CN- and F-) and cations (Fe3+, Cu2+ and Pd2+), with compound 7a being the most sensitive receptor for Fe3+ and Cu2+. On the other hand, compounds 5a, 7b and 7c were the most sensitive receptors for AcO-, CN- and F-. The binding stoichiometry between the receptors and the anions and cations was found to be 1:2 (ligand to anion/metal cation). The binding process was also followed by 1H NMR titrations. The evaluation of the TPA properties of chosen phenanthroimidazoles 7a-c by the two-photon induced fluorescence method revealed that compound 7c, which contains a bithienyl spacer, exhibited the highest TPA cross-section (σ2) value.

Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

Citrate trisulfonic acid: A heterogeneous organocatalyst for the synthesis of highly substituted Imidazoles

Citrate trisulfonic acid (CTSA), as a novel recyclable and eco-benign organocatalyst, was employed for the efficient and one-pot synthesis of trisubstituted imidazoles and tetrasubstituted imidazoles using aldehydes, ammonium acetate or aniline, and benzoin, benzyl, or 9,10-phenanthrenequinone under solvent-free conditions providing high to excellent yields. CTSA is easily prepared via the reaction of trisodium citrate and chlorosulfonic acid in high purity. Compared to the conventional procedures, the present method offers several advantages, including high yields, easy work-up, short reaction time, reusability of the catalyst, and simple purification of the products.