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2,9-Dichloro-1,10-phenanthroline is a chemical compound characterized by the molecular formula C12H6Cl2N2. It is a polyaromatic hydrocarbon derivative known for its strong chelating properties, which allow it to bind to metal ions and form stable complexes. This feature makes it a versatile reagent in various scientific disciplines, including chemistry, biochemistry, analytical chemistry, environmental science, and pharmaceuticals.

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  • 29176-55-4 Structure
  • Basic information

    1. Product Name: 2,9-Dichloro-1,10-phenanthroline
    2. Synonyms: 2,9-Dichloro-1,10-phenanthroline;1,10-Phenanthroline,2,9-dichloro-;2,9-Dichloro-o-phenanthroline;NSC 608430;VUF 7732;MFCD02084186;2,9-Dichloro-1,10-phenthroline
    3. CAS NO:29176-55-4
    4. Molecular Formula: C12H6Cl2N2
    5. Molecular Weight: 249.1
    6. EINECS: N/A
    7. Product Categories: Electronic Chemicals
    8. Mol File: 29176-55-4.mol
  • Chemical Properties

    1. Melting Point: 249-250℃
    2. Boiling Point: 417.3±40.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.482±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. PKA: 2.56±0.30(Predicted)
    10. CAS DataBase Reference: 2,9-Dichloro-1,10-phenanthroline(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2,9-Dichloro-1,10-phenanthroline(29176-55-4)
    12. EPA Substance Registry System: 2,9-Dichloro-1,10-phenanthroline(29176-55-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 29176-55-4(Hazardous Substances Data)

29176-55-4 Usage

Uses

Used in Chemical and Biochemical Research:
2,9-Dichloro-1,10-phenanthroline is used as a reagent in chemical and biochemical research for its ability to bind with metal ions, facilitating the study of metal ion interactions and their roles in various chemical processes.
Used in Analytical Chemistry:
In analytical chemistry, 2,9-Dichloro-1,10-phenanthroline is employed as a reagent for the detection and determination of certain metal ions in samples. Its chelating ability aids in the accurate measurement and identification of these ions.
Used as a Catalyst in Chemical Reactions:
2,9-Dichloro-1,10-phenanthroline is utilized as a catalyst in various chemical reactions due to its capacity to form stable complexes with metal ions, which can enhance the reaction rates and selectivity of certain processes.
Used in Environmental Science:
In environmental science, 2,9-Dichloro-1,10-phenanthroline is applied for the analysis and detection of metal ion pollutants, contributing to the assessment and monitoring of environmental contamination.
Used in Pharmaceutical Industry:
2,9-Dichloro-1,10-phenanthroline is also used in the pharmaceutical industry, where its chelating properties can be harnessed for the development of drugs that target metal ion-related biological processes or for the detection of metal ions in biological systems.
It is important to handle 2,9-Dichloro-1,10-phenanthroline with care and follow proper safety precautions due to its potential hazards and toxicity.

Check Digit Verification of cas no

The CAS Registry Mumber 29176-55-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,1,7 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 29176-55:
(7*2)+(6*9)+(5*1)+(4*7)+(3*6)+(2*5)+(1*5)=134
134 % 10 = 4
So 29176-55-4 is a valid CAS Registry Number.

29176-55-4 Well-known Company Product Price

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  • TCI America

  • (D4186)  2,9-Dichloro-1,10-phenanthroline  >97.0%(GC)(T)

  • 29176-55-4

  • 200mg

  • 950.00CNY

  • Detail
  • TCI America

  • (D4186)  2,9-Dichloro-1,10-phenanthroline  >97.0%(GC)(T)

  • 29176-55-4

  • 1g

  • 2,990.00CNY

  • Detail

29176-55-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,9-Dichloro-1,10-phenanthroline

1.2 Other means of identification

Product number -
Other names 2,9-dichloro-1,10-phenantroline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:29176-55-4 SDS

29176-55-4Relevant articles and documents

Synthesis of 2,9-Dichloro-1,10-phenanthroline from N,N'-Annelated Phenanthrolinediones

Yamada, Masaki,Nakamura, Yoshio,Kuroda, Shigeyasu,Shimao, Ichiro

, p. 2710 - 2712 (1990)

Though the chlorination of an N,N'-annelated phenanthrolinedione, 3,6,7,9-tetrahydro-5H-diazepinophenanthroline-3,9-dione, gave 2,9-dichloro-1,10-phenanthroline, another dione, 3,5,6,8-tetrahydropyrazinophenanthroline-3,8-dione, did not.It demonstrated a simultanous introduction of two chlorine substituents to non-substituted 1,10-phenanthroline via only the former intermediate.

Chemistry of Polydentate Ligands. Part 5. Complexes of 2,9-Dihydrazino-derivatives of 1,10-Phenanthroline. Dependence of Coordination Number of a Ligand on the Anion present

Lewis, Jack,O'Donoghue, Timothy D.

, p. 736 - 742 (1980)

Two quadridentate ligands have been prepared by rection of 2,9-dichloro-1,10-phenantroline with hydrazine hydrate and methylhydrazine.The formation of complexes of AgI, FII, MnII, ZnII, CdII, HgII, and NiII with these ligands is described.Electrical conductivity, i.r., and 1H n.m.r. spectral data of diamagnetic complexes are reported.The compound 2,9-dihydrazino-1,10-phenantroline can also act as a tridentate ligand, as in the complexes with nickel perchlorate, where the metal to ligand ratio is 1 : 2.Electronic spectral data of the nickel(II) complexes are presented.The preparation of a tridentate ligand, 2-(1-methylhydrazino)-1,10-phenantroline, and of nickel(II) and iron(II) complexes of this ligand is also reported.

Synthesis of Novel Chiral Phenanthroline Ligands and a Copper Complex

Li, Jian,Tang, Jingjing,Yang, Xueyan,Zhang, Zhipeng

, (2021/11/26)

A novel class of chiral multidentate ligands has been designed and synthesized from the important classic ligand 1,10-phenanthroline and amino acids. The ligands were proven to be able to coordinate with copper(2+) ion by the formation of a novel chiral c

Cu-tethered macrocycle catalysts: Synthesis and size-selective CO2-fixation to propargylamines under ambient conditions

Kim, Nam-Kyun,Sogawa, Hiromitsu,Takata, Toshikazu

, (2020/05/01)

A novel air-stable, Cu-tethered macrocycle catalyst possessing a large inner cavity was successfully synthesized, creating a unique supramolecular catalytic system. The catalyst was utilized in the CO2-fixation reaction to propargylamines. The reaction proceeded more efficiently compared to the conventional CuI catalyst under atmospheric CO2 condition. Notably, owing to its topological effect, the Cu-tethered macrocycle catalyst exhibited unique substrate size selectivity.

Ligand-Controlled Product Selectivity in Electrochemical Carbon Dioxide Reduction Using Manganese Bipyridine Catalysts

R?nne, Magnus H.,Cho, Dasol,Madsen, Monica R.,Jakobsen, Joakim B.,Eom, Seunghwan,Escoudé, émile,Hammersh?j, Hans Christian D.,Nielsen, Dennis U.,Pedersen, Steen U.,Baik, Mu-Hyun,Skrydstrup, Troels,Daasbjerg, Kim

, p. 4265 - 4275 (2020/03/05)

Electrocatalysis is a promising tool for utilizing carbon dioxide as a feedstock in the chemical industry. However, controlling the selectivity for different CO2 reduction products remains a major challenge. We report a series of manganese carbonyl complexes with elaborated bipyridine or phenanthroline ligands that can reduce CO2 to either formic acid, if the ligand structure contains strategically positioned tertiary amines, or CO, if the amine groups are absent in the ligand or are placed far from the metal center. The amine-modified complexes are benchmarked to be among the most active catalysts for reducing CO2 to formic acid, with a maximum turnover frequency of up to 5500 s-1 at an overpotential of 630 mV. The conversion even works at overpotentials as low as 300 mV, although through an alternative mechanism. Mechanistically, the formation of a Mn-hydride species aided by in situ protonated amine groups was determined to be a key intermediate by cyclic voltammetry, 1H NMR, DFT calculations, and infrared spectroelectrochemistry.

BIS-PHENANTHROLINE IRON MACROCYCLE COMPLEX FOR OXYGEN REDUCTION REACTION

-

, (2020/09/27)

Disclosed are compounds, compositions, and methods useful for the oxygen reduction reaction (ORR) and capable of operating efficiently at low overpotentials.

With the antibacterial activity of the substituted 2 - amido - 1, 10 - eurepium (by machine translation)

-

Paragraph 0026; 0029; 0030, (2019/06/07)

The invention relates to a compound of formula I is shown of a substituted 2 - amido - 1, 10 - eurepium antibacterial compound or its physiologically acceptable salt and their method of preparation, also relates to a pharmaceutical composition comprising said compound. Wherein each substituent defined as stated in claims. (by machine translation)

Synthesis, Structure, Property, and Dinuclear Cu(II) Complexation of Tetraoxacalix[2]arene[2]phenanthrolines

Wang, Xue-Yuan,Ao, Yu-Fei,Wang, Qi-Qiang,Wang, De-Xian

, p. 13461 - 13469 (2018/10/25)

A number of novel tetraoxacalix[2]arene[2]phenanthrolines 7-11 containing phenanthroline and diverse aromatic linkages were conveniently synthesized by a one-pot protocol between a series of dihydroxy arenes and 1,10-phenanthroline derivatives. Single-crystal diffraction analysis revealed that the resulting macrocycles possess diverse conformational and cavity structures which are regulated by the different aromatic linkages. In line with the length of the aromatic linkages, the distance between the two phenanthroline moieties (dN-N) gradually increases from 6.92 to 13.30 ?, respectively. The physicochemical properties of these macrocyclic compounds were investigated by spectroscopic, CV, and DPV measurements. Owing to the coordination ability of the phenanthroline moieties and the tunable conformational structure, the macrocyclic hosts can form distinct dinuclear complexation with Cu2+. Typically, with a short aromatic linkage the 7b-2Cu(II) complex gives an O-bridged dicopper structure, while with long linkage the 11b-2Cu(II) complex possesses two discrete copper centers. The spectroscopic structure and the redox property of the dicopper complexes were investigated by XPS, CV, and DPV techniques. This work hence provides a platform to access biomimetic copper-containing small-molecule models with well-defined structures.

Hard-and-soft phosphinoxide receptors for f-element binding: structure and photophysical properties of europium(iii) complexes

Borisova, Nataliya E.,Kharcheva, Anastasia V.,Patsaeva, Svetlana V.,Korotkov, Leonid A.,Bakaev, Sergey,Reshetova, Marina D.,Lyssenko, Konstantin A.,Belova, Elena V.,Myasoedov, Boris F.

, p. 2238 - 2248 (2017/02/26)

New phosphinoyl-containing tetradentate heterocycles preorganised for metal ion binding were designed and prepared in high yields. The X-ray structures of two allied phosphinoyl-bearing 2,2′-bipyridyl and phenanthroline ligands, as well as closely related structures of 2,6-bis(diphenylphosphinoyl)pyridine and 9-(diphenylphosphinoyl)-1,10-phenanthroline-2-one, are reported. Complexes of nitrates of several lanthanides and trifluoroacetate of Eu(iii) with two phosphinoyl-bearing 2,2′-bipyridyl and phenanthroline ligands were isolated and characterised. The first structures of lanthanide complexes with phosphinoyl-bearing 2,2′-bipyridyl and phenanthroline ligands are reported. The nature of the counter-ion is crucial for the coordination environment of the metal ion. The photophysical properties of the complexes differring in both the nature of the ligand and counter-ion were investigated. The photophysical properties of the complexes are strongly ligand- and counter-ion-dependent. Absorbance and luminescence excitation spectra of complexes showed main peaks in the UV range which correspond to the absorption of light by the ligand and these are ligand-dependent. Luminescence spectra of complexes show typical europium emission in the red region with a high quantum yield, which orresponds to the transitions5D0→7FJ (J = 0-6). The value of deviation of the components of5D0 →7F2 and5D0 →7F1 transitions from the inversion centre shows a larger dependence on the counter-ion than on the nature of the ligand. The value of the luminescence quantum yield is larger for europium complexes with 2,2′-bipyridyl-based ligands and NO3 counter-ions than for complexes with phenanthroline-based ligands and NO3 counter-ions. A low dependence of the luminescence lifetime of Eu complexes on the nature of the ligand has been demonstrated: values in the solid state were in the range 1.1-2.0 ms.

Synthesis and Characterization of a Ruthenium(II) Complex for the Development of Supramolecular Photocatalysts Containing Multidentate Coordination Spheres

Huber, Fabian L.,Nauroozi, Djawed,Mengele, Alexander K.,Rau, Sven

, p. 4020 - 4027 (2017/09/20)

The synthesis of the new bis-heteroleptic RuII complex [(tbbpy)2Ru(dptpphz)](PF6)2 (7), that exhibits a tetradentate coordination sphere for a second metal centre, and its characterization are presented. The complex shows similar photostability and redox properties regarding the first ligand-centred reductions compared to its tpphz analogue. Concentration-dependent NMR investigations were performed and a dimerization constant (KD = 83 ± 5) could be calculated, which was significantly lower than that of other tpphz systems. Photophysical investigations reveal a stabilizing effect of the two electron-withdrawing 2-pyridyl substituents on π–π* transition of the phenazine sphere. The typical H2O-induced light-switch effects have also been observed. To further highlight the potential of the tetradentate coordination site, the ZnII adduct of 7 was prepared and preliminary studied.

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