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5-Chloro-1,10-phenanthroline

CAS# 4199-89-7

5-Chloro-1,10-phenanthroline

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Quality Control of 5-Chloro-1,10-phenanthroline

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Chemical structure

5-Chloro-1,10-phenanthroline

3D structure

Chemical Properties of 5-Chloro-1,10-phenanthroline

Cas No. 4199-89-7 SDF Download SDF
PubChem ID 77865 Appearance Powder
Formula C12H7ClN2 M.Wt 214.65
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-chloro-1,10-phenanthroline
SMILES C1=CC2=CC(=C3C=CC=NC3=C2N=C1)Cl
Standard InChIKey XDUUQOQFSWSZSM-UHFFFAOYSA-N
Standard InChI InChI=1S/C12H7ClN2/c13-10-7-8-3-1-5-14-11(8)12-9(10)4-2-6-15-12/h1-7H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

5-Chloro-1,10-phenanthroline Dilution Calculator

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5-Chloro-1,10-phenanthroline Molarity Calculator

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Preparing Stock Solutions of 5-Chloro-1,10-phenanthroline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.6587 mL 23.2937 mL 46.5875 mL 93.1749 mL 116.4687 mL
5 mM 0.9317 mL 4.6587 mL 9.3175 mL 18.635 mL 23.2937 mL
10 mM 0.4659 mL 2.3294 mL 4.6587 mL 9.3175 mL 11.6469 mL
50 mM 0.0932 mL 0.4659 mL 0.9317 mL 1.8635 mL 2.3294 mL
100 mM 0.0466 mL 0.2329 mL 0.4659 mL 0.9317 mL 1.1647 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 5-Chloro-1,10-phenanthroline

Ruthenium bis-diimine complexes with a chelating thioether ligand: delineating 1,10-phenanthrolinyl and 2,2'-bipyridyl ligand substituent effects.[Pubmed:24325318]

Inorg Chem. 2014 Jan 6;53(1):294-307.

Despite the high pi-acidity of thioether donors, ruthenium(II) complexes with a bidentate 1,2-bis(phenylthio)ethane (dpte) ligand and two chelating diimine ligands (i.e., Ru(diimine)2(dpte)(2+)) exhibit room-temperature fluid solution emission originating from a lowest MLCT excited state (diimine = 2,2'-bipyridine, 5,5'-dimethyl-2,2'-bipyridine 4,4'-di-tert-butyl-2,2'-bipyridine, 1,10-phenanthroline, 5-methyl-1,10-phenanthroline, 5-Chloro-1,10-phenanthroline, 5-bromo-1,10-phenanthroline, 5-nitro-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, and 3,4,7,8-tetramethyl-1,10-phenanthroline). Crystal structures show that the complexes form 2 of the 12 possible conformational/configurational isomers, as well as nonstatistical distributions of geometric isomers; there also are short intramolecular pi-pi interactions between the diimine ligands and dpte phenyl groups. The photoinduced solvolysis product, [Ru(diimine)2(CH3CN)2](PF6)2, for one complex in acetonitrile also was characterized by single-crystal X-ray diffraction. Variations in the MLCT energies and Ru(III/II) redox couple, E degrees '(Ru(3+/2+)), can be understood in terms of the influence of the donor properties of the ligands on the mainly metal-based HOMO and mainly diimine ligand-based LUMO. E degrees '(Ru(3+/2+)) also is quantitatively described using a summative Hammett parameter (sigmaT), as well as using Lever's electrochemical parameters (EL). Recommended parametrizations for substituted 2,2'-bipyridyl and 1,10-phenanthrolinyl ligands were derived from analysis of correlations of E degrees '(Ru(3+/2+)) for 99 homo- and heteroleptic ruthenium(II) tris-diimine complexes. This analysis reveals that variations in E degrees '(Ru(3+/2+)) due to substituents at the 4- and 4'-positions of bipyridyl ligands and 4- and 7-positions of phenanthrolinyl ligands are significantly more strongly correlated with sigmap(+) than either sigmam or sigmap. Substituents at the 5- and 6-positions of phenanthrolinyl ligands are best described by sigmam and have effects comparable to those of substituents at the 3- and 8-positions. Correlations of EL with sigmaT for 1,10-phenanthrolinyl and 2,2'-bipyridyl ligands show similar results, except that sigmap and sigmap(+) are almost equally effective in describing the influence of substituents at the 4- and 4'-positions of bipyridyl ligands. MLCT energies and d(5)/d(6)-electron redox couples of the complexes with 5-substituted 1,10-phenanthroline exhibit correlations with values for other d(6)-electron metal complexes that can be rationalized in terms of the relative number of diimine ligands and substituents.

1,10-Phenanthrolinium ionic liquid crystals.[Pubmed:21250740]

Langmuir. 2011 Mar 1;27(5):2036-43.

The 1,10-phenanthrolinium cation is introduced as a new building block for the design of ionic liquid crystals. 1,10-Phenanthroline, 5-methyl-1,10-phenanthroline, 5-Chloro-1,10-phenanthroline, and 4,7-diphenyl-1,10-phenanthroline were quaternized by reaction with 1,3-dibromopropane or 1,2-dibromoethane. The resulting cations were combined with dodecyl sulfate or dioctyl sulfosuccinate anions. The influence of both the cation and anion type on the thermal behavior was investigated. Several of the complexes exhibit mesomorphic behavior, with smectic E phases for the dodecyl sulfate salts and smectic A phases for the dioctyl sulfosuccinate salts. Structural models for the packing of the 1,10-phenanthrolinium and anionic moieties in the liquid-crystalline phases are presented. The ionic compounds show fluorescence in the solid state and in solution.

Encapsulation of platinum(II)-based DNA intercalators within cucurbit[6,7,8]urils.[Pubmed:17653578]

J Biol Inorg Chem. 2007 Sep;12(7):969-79.

The partial encapsulation of platinum(II)-based DNA intercalators of the type [Pt(5-Cl-phen)(ancillary ligand)](2+), where 5-Cl-phen is 5-Chloro-1,10-phenanthroline and the ancillary ligand is ethylenediamine, (1S,2S)-diaminocyclohexane (S,S-dach) or (1R,2R)-diaminocyclohexane, within cucurbit[n]uril (CB[n], where n is 6, 7 or 8) has been examined by (1)H and (195)Pt NMR and mass spectrometry. For CB[7], the molecule encapsulates over the ancillary ligand of all metal complexes, whether this is ethylenediamine or diaminocyclohexane. For CB[8], encapsulation occurs over the sides of the 5-Cl-phen ligand at low [Pt(5-Cl-phen)(S,S-dach)](2+) (5CLSS) to CB[8] ratios (i.e. 0.25:1) but over the ancillary ligand at higher ratios (i.e. 2:1). For CB[6] binding, 5CLSS exhibits both portal and cavity binding, with the ancillary ligand displaying chemical shifts consistent with fast exchange kinetics on the NMR timescale for portal binding and slow exchange kinetics for cavity binding. Binding constants could not be determined using UV-vis, circular dichroism or fluorescence spectrophotometry, but a binding constant for binding of 5CLSS to CB[6] of approximately 10(5) M(-1) was determined using (1)H NMR. Finally, the effect of CB[n] encapsulation on the cytotoxicity of the metal complexes was examined using L1210 murine leukaemia cells in vitro growth inhibition assays. The cytotoxicity is highly dependent on both the metal complex and the CB[n] size, and whilst CB[7] and CB[8] generally decreased cytotoxicity, it was found that CB[6] increased the cyotoxicity of 5CLSS up to 2.5-fold.

Luminescence of LnIII dithiocarbamate complexes (Ln = La, Pr, Sm, Eu, Gd, Tb, Dy).[Pubmed:18247543]

Inorg Chem. 2008 Mar 3;47(5):1512-23.

We have discovered room temperature photoluminescence in Sm3+ and Pr3+ dithiocarbamate complexes. Surprisingly, these complexes exhibit more intense emission than those of the Eu3+, Tb3+, and Dy3+ analogues. The electronic absorption, excitation, and emission spectra are reported for the complexes [Ln(S2CNR2)3L] and NH2Et2[Ln(S2CNEt2)4], where Ln = Sm, Pr; R = ethyl, ibutyl, benzyl; and L = 1,10-phenanthroline, 2,2'-bipyridine, and 5-Chloro-1,10-phenanthroline. The lowest ligand-localized triplet energy level (T1) of the complexes are determined from the phosphorescence spectra of analogous La3+ and Gd3+ chelates. The luminescence decay curves were measured to determine the excited-state lifetimes for the Pr3+ and Sm3+ complexes. X-ray crystal structures of Sm(S2CNiBu2)3phen, Pr(S2CNEt2)3phen, and Pr(S2CNiBu2)3phen are also reported.

The effect of ancillary ligand chirality and phenanthroline functional group substitution on the cytotoxicity of platinum(II)-based metallointercalators.[Pubmed:17544512]

J Inorg Biochem. 2007 Jul;101(7):1049-58.

Fifteen platinum(II)-based metallointercalators have been synthesised that utilise substituted 1,10-phenanthroline (phen) ligands, including 5-Chloro-1,10-phenanthroline (5-Cl-phen), 5-methyl-1,10-phenanthroline (5-CH3-phen), 5-amino-1,10-phenanthroline (5-NH2-phen), 5-nitro-1,10-phenanthroline (5-NO2-phen) and dipyrido[3,2-d:2',3'-f]quinoxaline (dpq), and achiral ethylenediamine (en) and the chiral ancillary ligands 1S,2S-diaminocyclohexane (S,S-dach) and 1R,2R-diaminocyclohexane (R,R-dach). Their cytotoxicity in the L1210 murine leukaemia cell line was determined using growth inhibition assays. The most cytotoxic metal complexes are those that contain S,S-dach ancillary ligands and 5-CH3-phen intercalating ligands. One metallointercalator [Pt(5-CH3-phen)(S,S-dach)]Cl2 (5MESS), displays a 5-10-fold increase in cytotoxicity compared to the clinical agent cisplatin. From DNA binding experiments there appears to be no significant difference between any of the metal complexes, indicating that neither DNA binding affinity nor the mode of binding/DNA adduct formed is the sole determinant of the cytotoxicity of this family of platinum(II)-based metallointercalators.

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