3002-77-5

Basic information

• Product Name: 2-methyl-1,10-phenanthroline
• Synonyms: 2-methyl-1,10-phenanthroline;1,10-Phenanthroline,2-Methyl-
• CAS NO: 3002-77-5
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.23
• EINECS: 1312995-182-4
• Product Categories: MOFS COFS
• Mol File: 3002-77-5.mol

Chemical Properties

• Melting Point: 50-53 °C
• Boiling Point: 175°C/0.2mmHg(lit.)
• Flash Point: 161.376 °C
• Appearance: /
• Density: 1.211 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.63±0.40(Predicted)
• CAS DataBase Reference: 2-methyl-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-1,10-phenanthroline(3002-77-5)
• EPA Substance Registry System: 2-methyl-1,10-phenanthroline(3002-77-5)

Safety Data

• Hazardous Substances Data: 3002-77-5(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2-methyl-1,10-phenanthroline is used as a chelating agent for forming stable complexes with metal ions, which is essential in various analytical processes.
Used in Molecular Biology:
2-methyl-1,10-phenanthroline is used as a biochemical tool for in vitro studies, contributing to the understanding of molecular interactions and mechanisms.
Used in Biochemistry:
2-methyl-1,10-phenanthroline is used as a reagent in biochemical research, aiding in the investigation of enzyme activity and other biological processes.

Upstream product

• 18978-78-4 2-methyl-8-aminoquinoline 
• 56-81-5 glycerol 
• 66-71-7 1,10-Phenanthroline 
• 917-54-4 methyllithium 
• 29176-56-5 1,9-dimethyl-1,10-phenanthrolinium iodide 
• 578-66-5 8-amino quinoline 
• 123-73-9 trans-Crotonaldehyde 
• 815-68-9 3-acetylpentane-2,4-dione 
• 158753-17-4 8-amino-7-quinolinecarbaldehyde 
• 75-24-1 trimethylaluminum 
• 109-92-2 ethyl vinyl ether 
• 123-73-9 crotonaldehyde 
• 88-74-4 2-nitro-aniline 
• 881-07-2 8-nitroquinaldine 

Downstream Products

• 33795-37-8 1,10-phenanthroline-2-carboxyaldehyde 
• 129008-23-7 2-methyl-9-phenyl-1,10-phenanthroline 
• 876127-06-9 [(2-formyl-1,10-phenanthroline 2,6-diethylanil)]FeCl₂ 
• 876126-86-2 2-formyl-1,10-phenanthroline(2,6-diethylanil) 
• 57154-80-0 1,10-phenanthroline-2-carboxylic acid chloride 
• 1891-17-4 1,10-phenanthroline-2-carboxylic acid 
• 885622-44-6 [(2-methylphenanthroline)(acetonitrile)platinum(II)methyl][B(3,5-(CF₃)2C₆H₃)4] 
• 119743-71-4 PtClMe(2-Me-1,10-phenanthroline)(C₂H₄) 
• 75-18-3 dimethylsulfide 
• 119743-72-5 PtClMe(2-Me-1,10-phenanthroline) 
• 850913-06-3 (S,S,S)-1-(3-methyl-10,11,12,13-tetrahydrodipyrido[3,2-a:2',3'-c]phenazine)-4,7,10-tris[N-(1-phenylethyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 

Relevant articles and documents

Synthesis of 1,10-phenanthrolines fused with bicyclo[3.3.0]octane and bicyclo[3.3.1]nonane frameworks

Reactions of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.0]octane-3,7- dione with 8-amino-7-quino-linecarbaldehyde under basic conditions led to fused nonplanar compounds with one or two 1,10-phenanthroline moieties. The novel heterocyclic systems bicy

Synthesis of α-fluoroimines by copper-catalyzed reaction of diarylacetylenes and n-fluorobenzenesulfonimide

Difunctionalization of unsaturated bonds with fluorinating reagents has been regarded as an efficient route to vicdifunctional organic fluorides. Here we report a coppercatalyzed synthesis of α-fluoroimines from diarylacetylenes and N-fluorobenzenesulfonimide. Mechanistically, the reaction initiates from the generation of imidyl radical, which reacts with alkyne to give the product. The resulting α-fluoroimine can easily be transformed into other organic fluorides such as fluoroketone and fluoroamines.

N ortho acyl substituted nitrogen-containing heterocyclic compound and process for preparing aminal iron (II) complexes thereof

Provided are a process for preparing an N ortho acyl substituted nitrogen-containing heterocyclic compound and an aminal iron (II) complex thereof, and the use of the complexes obtained by the process in an olefin oligomerization catalyst. The N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is for example 2-acyl-1,10-phenanthroline or 2,6-diacetyl pyridine as shown in formula b, and the N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is produced by a reaction of a precursor thereof in a substituted or unsubstituted nitrobenzene. Preferably the precursor shown in formula I in the present invention is produced by 1,10-phenanthroline reacting with trialkyl aluminum, or a halogenoalkyl aluminum RnAIXm, or a substituted or unsubstituted benzyl lithium Ph′CH2Li, followed by hydrolysis. The preparation method provided in the present invention has a few synthetic steps, an easy process, a low toxic effect, and reduces the preparation costs of the catalyst, and has a promising outlook in the industrial application.

1H NMR spectroscopic elucidation in solution of the kinetics and thermodynamics of spin crossover for an exceptionally robust Fe2+ complex

A series of Fe2+ spin crossover (SCO) complexes [Fe(5/6)]2+ employing hexadentate ligands (5/6) with cis/trans-1,2-diamino cyclohexanes (4) as central building blocks were synthesised. The ligands were obtained by reductive amination of 4 with 2,2′-bipyridyl-6-carbaldehyde or 1,10-phenanthroline-2-carbaldehyde 3. The chelating effect and the rigid structure of the ligands 5/6 lead to exceptionally robust Fe2+ and Zn2+ complexes conserving their structure even in coordinating solvents like dmso at high temperatures. Their solution behavior was investigated using variable temperature (VT) 1H NMR spectroscopy and VT Vis spectroscopy. SCO behavior was found for all Fe2+ complexes in this series centred around and far above room temperature. For the first time we have demonstrated that the thermodynamics as well as kinetics for SCO can be deduced by using VT 1H NMR spectroscopy. An alternative scheme using a linear correction term C1 to model chemical shifts for Fe2+ SCO complexes is presented. The rate constant for the SCO of [Fe(rac-trans-5)]2+ obtained by VT 1H NMR was validated by Laser Flash Photolysis (LFP), with excellent agreement (1/(kHL + kLH) = 33.7/35.8 ns for NMR/LFP). The solvent dependence of the transition temperature T1/2 and the solvatochromism of complex [Fe(rac-trans-5)]2+ were ascribed to hydrogen bond formation of the secondary amine to the solvent. Enantiomerically pure complexes can be prepared starting with R,R- or S,S-1,2-diaminocyclohexane (R,R-trans-4 or S,S-trans-4). The high robustness of the complexes reduces a possible ligand scrambling and allows preparation of quasiracemic crystals of [Zn(R,R-5)][Fe(S,S-5)](ClO4)4·(CH3CN) composed of a 1:1 mixture of the Zn and Fe complexes with inverse chirality.

Steric vs electronic effects and solvent coordination in the electrochemistry of phenanthroline-based copper complexes

The present exhaustive electrochemical study proposes a rationalization of the redox properties of 1,10-phenanthroline-based copper complexes as a function of i) ligand molecular structure, evidencing the competition between electronic and steric effects of alkyl/aryl substituents, and ii) nature of working medium in terms of both solvent and supporting electrolyte anion. Occupancy of the 2 and 9 positions of the phenanthroline is a powerful tool to modulate the oxidation potentials of this family of complexes in a wide potential range. Solvent molecules play a key role in the metal-centred oxidative electron transfer process (unlike the optical electron transition), acting as ancillary ligands that allow the transition between tetrahedral four-coordinated Cu(I) state to tetragonal five-coordinated Cu(II). Actually clear evidences of the entry of one solvent molecule in the inner coordination sphere of the complexes are proved by the Kolthoff and Lingane method. Proof of ionic couple formation is also found.

Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach

The synthesis of 8-aminoquinolines and 1,10-phenanthrolines with substituents in α of the nitrogen has been performed through an inverse-demanding aza-Diels-Alder (Povarov reaction) in the fluoroalcohols TFE or HFIP. This path involves simple starting materials: 1,2-phenylenediamines, enol ethers and aldehydes.

New nonsymmetric phenanthrolines as very effective ligands in the palladium-catalyzed carbonylation of nitrobenzene

Inspired by the results of a previous mechanistic study, a series of mostly new nonsymmetric phenanthrolines were synthesized and tested as ligands in the palladium-catalyzed reductive carbonylation reaction of nitrobenzene to methyl phenylcarbamate. Very good results were obtained when the asymmetry was of an electronic nature (a donating substituent in the para position of one of the two pyridinic rings and an electron-withdrawing or no substituent on the para position of the other pyridinic ring), but steric hindrance in the ortho or meta position retarded the reaction. The TOF for the modified system is the highest ever reported for any carbonylation reaction of nitroarenes.

A new approach to the 1,10-phenanthroline core

A protocol for the synthesis of substituted 1,10-phenanthrolines is reported. The phenanthroline scaffold has been obtained constructing the central cycle starting from two pyridine rings. The method is hinged upon the intramolecular coupling of cis-1,2-di(2-bromo-3-pyridyl)ethenes that are in turn obtained from the Wittig reaction of 2-bromonicotinaldehydes with phosphonium salts prepared from 2-bromo-3-(bromomethyl)pyridines. Yields up to 75% have been obtained.

Friedlaender reactions of triacetylmethane- unusual distribution of products-

Friedlaender reactions of triacetylmethane with selected β-amino-α,β-unsaturated aldehydes afforded pyridoheterocycles and their 2-methyl derivatives instead of triheteroarylmethane.

Synthesis and characterisation of highly emissive and kinetically stable lanthanide complexes suitable for usage 'in cellulo'

The synthesis and photophysical characterisation are reported of a series of cationic, neutral and anionic europium and terbium complexes based on structurally related, nonadentate ligands based on the cyclen macrocycle. Each complex incorporates a tetraazatriphenylene moiety and overall absolute emission quantum yields are in the range 15-40% in aerated aqueous media. Dynamic quenching of the lanthanide excited state occurs with electron-rich donors, e.g. iodide, ascorbate and urate, and a mechanistic interpretation is put forward involving an electron transfer process. The cationic lanthanide complexes are taken up by N1H/3T3 cells and tend to localise inside the cell nucleus. The Royal Society of Chemistry 2005.