3248-05-3

Basic information

• Product Name: 4,7-Dimethyl-1,10-phenanthroline
• Synonyms: 4,7-DIMETHYL-1,10-PHENANTHROLINE;TIMTEC-BB SBB008716;1,10-Phenanthroline, 4,7-dimethyl-;4,7-dimethyl-10-phenanthroline;4,7-Dimethyl-o-phenanthroline;4,7-DIMETHYL-1,10-PHENANTHROLINE ANHYDROUS;1,8-Dimethyl-4,5-diazaphenanthrene;4,7-diMethy-1,10-phenathroline(Monohydrate)
• CAS NO: 3248-05-3
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208.26
• EINECS: 221-827-5
• Mol File: 3248-05-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 338.63°C (rough estimate)
• Flash Point: 176.9 °C
• Appearance: /
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 3.63E-06mmHg at 25°C
• Refractive Index: 1.6152 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.01±0.10(Predicted)
• Water Solubility: Soluble in benzene and alcohol. Slightly soluble in water.
• CAS DataBase Reference: 4,7-Dimethyl-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-Dimethyl-1,10-phenanthroline(3248-05-3)
• EPA Substance Registry System: 4,7-Dimethyl-1,10-phenanthroline(3248-05-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3248-05-3(Hazardous Substances Data)

Usage

Uses

Used in Synthetic Chemistry and Dye Industry:
4,7-Dimethyl-1,10-phenanthroline is used as an intermediate in synthetic chemistry for the production of various organic compounds and dyes. Its unique structure allows it to participate in a range of chemical reactions, contributing to the synthesis of a diverse array of products.
Used as an Organic Bidentate Ligand:
In coordination chemistry, 4,7-Dimethyl-1,10-phenanthroline serves as an organic bidentate ligand, forming stable complexes with metal ions. This property is crucial for various analytical and industrial applications, including the development of catalysts and the creation of metal complexes with specific properties.
Used in Detection and Analytical Chemistry:
4,7-Dimethyl-1,10-phenanthroline is utilized in the detection of metal ions through the formation of colored complexes. This characteristic makes it a valuable tool in analytical chemistry for the qualitative and quantitative analysis of metal ions in various samples.
Used in Colorimetric Sensors:
4,7-Dimethyl-1,10-phenanthroline plays a significant role in the development of colorimetric sensors, which are devices that change color in response to specific stimuli. The color change upon interaction with metal ions allows for the visual detection and quantification of target analytes.
Used in Coordination Polymers:
4,7-Dimethyl-1,10-phenanthroline is a key component in the formation of coordination polymers, which are materials with repeating structural units connected by metal ions and organic ligands. These polymers have potential applications in areas such as catalysis, gas storage, and drug delivery.
Used in Ionochromism:
4,7-Dimethyl-1,10-phenanthroline contributes to the field of ionochromism, which involves the color change of a substance upon interaction with ions. This property is useful in the development of materials that can visually indicate the presence of specific ions, such as in environmental monitoring or security applications.
Used in Luminescence Applications:
4,7-Dimethyl-1,10-phenanthroline is also involved in luminescent materials, which emit light upon excitation. 4,7-Dimethyl-1,10-phenanthroline's ability to form complexes with metal ions can lead to the development of luminescent materials with potential applications in sensing, imaging, and optoelectronics.

InChI:InChI=1/C14H12N2/c1-9-5-7-15-13-11(9)3-4-12-10(2)6-8-16-14(12)13/h3-8H,1-2H3

Upstream product

• 78-94-4 methyl vinyl ketone 
• 95-54-5 1,2-diamino-benzene 
• 366-18-7 [2,2]bipyridinyl 
• 7647-01-0 hydrogenchloride 
• 6322-49-2 4-chloro-2-butanone 
• 7705-08-0 iron(III) chloride 
• 88-74-4 2-nitro-aniline 
• 6139-84-0 4-chlorobutyraldehyde 
• 62748-01-0 4-methyl-8-aminoquinoline 
• 6607-66-5 1,3,3-trimethoxybutane 

Downstream Products

• 51786-72-2 4,7-dimethyl-2,9-diphenyl-[1,10]phenanthroline 
• 229622-27-9 [Cu(4,7-dimethyl-1,10-phenanthroline)(salicylaldehydate)]NO₃ 
• 106017-66-7 Cu(C₁₂H₆N₂(CH₃)2)(P(C₆H₅)3)2⁽¹⁺⁾*SO₃CF₃^(1-)=(Cu(C₁₂H₆N₂(CH₃)2)(P(C₆H₅)3)2)SO₃CF₃ 
• 31301-31-2 1,10-phenanthroline-4,7-dicarboxylic acid 
• 366-18-7 [2,2]bipyridinyl 
• 130897-87-9 4,7-dicarboxaldehyde-1,10-phenanthroline 

Relevant articles and documents

Carbon-hydrogen bond breaking and making in the open-shell singlet molecule Cp2Yb(4,7-Me2phen)

The adducts formed between the 4,7-Me2-, 3,4,7,8-Me4-, and 3,4,5,6,7,8-Me6-phenanthroline ligands and Cp2Yb are shown to have open-shell singlet ground states by magnetic susceptibility and LIII-edge XANES spectroscopy. Variable-temperature XANES data show that two singlet states are occupied in each adduct that are fit to a Boltzmann distribution for which δH = 5.75 kJ mol-1 for the 4,7-Me2phen adduct. The results of a CASSCF calculation for the 4,7-Me2phen adduct indicates that three open-shell singlet states, SS1-SS3, lie 0.44, 0.06. and 0.02 eV, respectively, below the triplet state. These results are in dramatic contrast to those acquired for the phenanthroline and 5,6-Me2phen adducts, which are ground state triplets (J. Am. Chem. Soc. 2014, 136, 8626). A model that accounts for these differences is traced to the relative energies of the LUMO and LUMO+1 orbitals that depend on the position the methyl group occupies in the phenanthroline ligand. The model also accounts for the difference in reactivities of Cp2Yb(3,8-Me2phen) and Cp2Yb(4,7-Me2phen); the former forms a σ C-C bond between C(4)C(4′), and the latter undergoes C-H bond cleavage at the methyl group on C(4) and leads to two products that cocrystallize: Cp2Yb(4-(CH2),7-Mephen), which has lost a hydrogen atom, and Cp2Yb(4,7-Me2-4H-phen), which has gained a hydrogen atom.

Color responses of novel receptors for AcO- and a test paper for AcO- in pure aqueous solution

An efficient AcO- sensor L which contains 1,10-phenanthroline-based and nitrophenylhydrazine-based groups, and its water-soluble Ru(II) complex were synthesized, characterized and studied in this Letter. Via UV-vis experiments and 1H NMR titration in DMSO solution, it was found that there were potential hydrogen bonds between the N{double bond, long}CH and AcO- after the deprotanation of two -NH during the reaction of L or its Ru complex with anions. Furthermore, an easy-to-prepare test paper was developed to detect AcO- at 10 mg/L in pure aqueous solution.

Thermodynamic studies of the binding of bidentate nitrogen donors with methyltrioxorhenium (MTO) in CHCl3 solution

Methyltrioxorhenium (MTO) adduct formation with bidentate nitrogen donors 2,2′-bipyridine (bpy), 4,4′-dimethyl-2,2′-bipyridine (Me 2bpy), 4,4′-di-tert-butyl-2,2′-bipyridine ( tBu2bpy), 1,10-phenanthroline (phen), 5-methyl-

Production method of a cross-coupling compound from an alkyl halide and an organoboron compound

There is provided a method for producing a coupling compound of formula (1):(Y-)(n-1)R1-R2-(R1)(n'-1) wherein R1, R2 n and n' are as defined below, Y is R2 or X as defined below, which method comprises reactinganorganichalogen compound of formula (2):n' (R1X1n) wherein X1 represents a bromine or iodine, R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which α and β carbon atoms in relation to X1 are sp3 carbon atoms, n and n' each independently represent an integer of 1 or 2, and provided that n and n' do not simultaneously represent 2, with an organic boron compound of formula (3):m{R2(BX22)n'} wherein R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group and the boron atom is bonded with an sp2 carbon atom thereof, X2 represents a hydroxyl or alkoxy group, n' is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, and ???b) b-1) a compound of formula (i): ???or ???b-2) a compound of formula (ii):

Catalyst compositions and a process for polymerizing carbon monoxide and olefins

Carbon monoxide and at least one olefinically unsaturated organic compound may be polymerized by contacting the monomers in the presence of a catalyst which comprises a Group VIII metal compound of palladium, cobalt or nickel, a halide of tin or germanium, a nitrogen bidentate ligand and an organic oxidant. The polymers prepared are linear alternating polymers which consist of units with the formula STR1 where A is the residue of an alkenically unsaturated organic compound monomer.

A Simple Synthesis of Some 1,10-Phenanthrolines

The reaction of o-phenylenediamine with α,β-unsaturated ketones in the presence of hydrochloric acid smoothly affords alkyl substituted 1,10-phenanthrolines in a one step synthesis.