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2,2'-(5-bromo-1,3-phenylene)dipyridine is a chemical compound characterized by the molecular formula C16H10BrN2. It is a bidentate ligand that plays a significant role in coordination chemistry and the construction of metal-organic frameworks. 2,2'-(5-broMo-1,3-phenylene)dipyridine is recognized for its capacity to form robust coordinate bonds with metal ions, which is facilitated by its structural composition of two pyridine rings linked by a 5-bromo-1,3-phenylene bridge. The presence of the bromo substituent endows the compound with reactivity and adaptability for additional functionalization, making it a valuable component in the synthesis of coordination polymers and supramolecular assemblies. Furthermore, its capability to create stable complexes with transition metal ions positions it as a useful agent in catalytic processes and optical applications.

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  • 150239-89-7 Structure
  • Basic information

    1. Product Name: 2,2'-(5-broMo-1,3-phenylene)dipyridine
    2. Synonyms: 2,2'-(5-broMo-1,3-phenylene)dipyridine;Pyridine, 2,2'-(5-bromo-1,3-phenylene)bis-
    3. CAS NO:150239-89-7
    4. Molecular Formula: C16H11BrN2
    5. Molecular Weight: 311.17594
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 150239-89-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 421.5±35.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.397±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 4.13±0.31(Predicted)
    10. CAS DataBase Reference: 2,2'-(5-broMo-1,3-phenylene)dipyridine(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2,2'-(5-broMo-1,3-phenylene)dipyridine(150239-89-7)
    12. EPA Substance Registry System: 2,2'-(5-broMo-1,3-phenylene)dipyridine(150239-89-7)
  • 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: 150239-89-7(Hazardous Substances Data)

150239-89-7 Usage

Uses

Used in Coordination Chemistry:
2,2'-(5-bromo-1,3-phenylene)dipyridine is utilized as a bidentate ligand for the formation of coordination polymers and supramolecular assemblies. Its ability to form strong coordinate bonds with metal ions is instrumental in creating stable and functional structures in this field.
Used in Metal-Organic Frameworks (MOFs):
In the development of MOFs, 2,2'-(5-bromo-1,3-phenylene)dipyridine serves as a crucial building block. Its incorporation into MOFs enhances their structural integrity and potential applications in areas such as gas storage, catalysis, and drug delivery.
Used in Catalysis:
2,2'-(5-bromo-1,3-phenylene)dipyridine is employed as a ligand in the creation of catalytic systems. Its interaction with transition metal ions results in the formation of active sites that can facilitate various chemical reactions, thereby enhancing the efficiency and selectivity of catalytic processes.
Used in Optical Applications:
2,2'-(5-broMo-1,3-phenylene)dipyridine is also used in optical applications due to its ability to form complexes with metal ions. These complexes can exhibit unique optical properties, making them suitable for use in areas such as sensors, photonic devices, and luminescent materials.
Used in Chemical Synthesis:
2,2'-(5-bromo-1,3-phenylene)dipyridine is utilized as a reagent or intermediate in the synthesis of other organic compounds and pharmaceuticals, taking advantage of its reactivity and the bromo substituent for further functionalization.

Check Digit Verification of cas no

The CAS Registry Mumber 150239-89-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,0,2,3 and 9 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 150239-89:
(8*1)+(7*5)+(6*0)+(5*2)+(4*3)+(3*9)+(2*8)+(1*9)=117
117 % 10 = 7
So 150239-89-7 is a valid CAS Registry Number.

150239-89-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2'-(5-bromo-1,3-phenylene)dipyridine

1.2 Other means of identification

Product number -
Other names 3,5-bis(pyridin-2-yl)-1-bromobenzene

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:150239-89-7 SDS

150239-89-7Relevant articles and documents

Excimer-Monomer Photoluminescence Mechanochromism and Vapochromism of Pentiptycene-Containing Cyclometalated Platinum(II) Complexes

Lin, Che-Jen,Liu, Yi-Hung,Peng, Shie-Ming,Shinmyozu, Teruo,Yang, Jye-Shane

, p. 4978 - 4989 (2017)

The ability of the bulky H-shaped pentiptycene scaffold in promoting the mechanochromic and vapochromic luminescence properties for organometallic materials has been demonstrated with the N^C^N cyclometalated platinum(II) complexes [X-NCNPtY], where X = Br or Pa, the substituent on the terdentate dipyridylbenzene N^C^N ligand, and Y = Cl or Pa, the ancillary ligand, in which Pa = pentiptycene acetylene. Intermolecular interactions between the planar NCNPt cores are described by π-π and d?π interactions with negligible PtII···PtII bonding, corresponding to ligand-centered excimer rather than metal-metal-to-ligand charge-transfer emission, for these platinum(II) complexes in aggregates and in the solid state. Interplay of the relative excimer-to-monomer emission intensity in response to external force and/or vapor stimuli accounts for the luminescence mechanochromism and vapochromism of the pentiptycene-incorporated platinum(II) complexes [Pa-NCNPtCl], [Br-NCNPtPa], and [Pa-NCNPtPa], whereas the pentiptycene-free counterpart [Br-NCNPtCl] undergoes little or no emission color response. In particular, the complex [Pa-NCNPtCl] displays a distinct response to aromatic versus nonaromatic organic vapors: namely, aromatic vapors such as benzene convert the excimer emission to monomer emission, but the opposite is true with nonaromatic vapors. A two-stage emission color change from red to orange and then to yellow could thus be achieved by grinding and by subsequent benzene-vapor fuming. Another feature associated with [Pa-NCNPtCl] is an aggregation-induced green → magenta luminescence color change in water/tetrahydrofuran mixed solutions. The structure-luminescence property relationship is discussed in relation to intermolecular interactions and packing modes that depend on the number and positions of pentiptycene groups.

Transition from a Metal-Localized Mixed-Valence Compound to a Fully Delocalized and Bridge-Biased Electrophore in a Ruthenium–Amine–Ruthenium Tricenter System

Tang, Jian-Hong,Shao, Jiang-Yang,He, Yan-Qin,Wu, Si-Hai,Yao, Jiannian,Zhong, Yu-Wu

, p. 10341 - 10345 (2016)

A series of cyclometalated diruthenium complexes with a redox-active amine bridge were synthesized. Depending on the terminal ligands of the ruthenium components and the substituent on the amine unit, the one-electron-oxidized state can be either in the f

ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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Paragraph 0359-0360, (2018/12/02)

Provided are an organometallic compound and an organic light-emitting device including the organometallic compound. The organometallic compound may be represented by Formula 1. In Formula 1, L1 may be a ligand represented by Formula 2A or 2B, and L2 may be a monovalent organic ligand or a divalent organic ligand.

Condensed compound and organic light emitting diode comprising the same

-

Paragraph 0432; 0434; 0435, (2016/10/10)

Disclosed are a condensed ring compound and an organic light emitting diode. The organic light emitting diode has low driving voltage, high efficiency, high brightness, and long life. The organic light emitting diode includes a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, and including a light emitting layer, wherein the organic layer includes one or more kind of condensed ring compound of any one claim among a first claim to 15^th claim.COPYRIGHT KIPO 2015

Synthesis and self-assembly of NCN-pincer Pd-complex-bound norvalines

Ogata, Kazuki,Sasano, Daisuke,Yokoi, Tomoya,Isozaki, Katsuhiro,Yoshida, Ryota,Takenaka, Toshio,Seike, Hirofumi,Ogawa, Tetsuya,Kurata, Hiroki,Yasuda, Nobuhiro,Takaya, Hikaru,Nakamura, Masaharu

, p. 12356 - 12375 (2013/09/23)

The NCN-pincer Pd-complex-bound norvalines Boc-D/L-[PdCl(dpb)]Nva-OMe (1) were synthesized in multigram quantities. The molecular structure and absolute configuration of 1 were unequivocally determined by single-crystal X-ray structure analysis. The robustness of 1 under acidic/basic conditions provides a wide range of N-/C-terminus convertibility based on the related synthetic transformations. Installation of a variety of functional groups into the N-/C-terminus of 1 was readily carried out through N-Boc- or C-methyl ester deprotection and subsequent condensations with carboxylic acids, R 1COOH, or amines, R2NH2, to give the corresponding N-/C-functionalized norvalines R1-D/L-[PdCl(dpb)]Nva- R2 2-9. The dipeptide bearing two Pd units 10 was successfully synthesized through the condensation of C-free 1 with N-free 1. The robustness of these Pd-bound norvalines was adequately demonstrated by the preservation of the optical purity and Pd unit during the synthetic transformations. The lipophilic Pd-bound norvalines L-2, Boc-L-[PdCl(dpb)]Nva-NH-n-C 11H23, and L-4, n-C4H9CO-L- [PdCl(dpb)]Nva-NH-n-C11H23, self-assembled in aromatic solvents to afford supramolecular gels. The assembled structures in a thermodynamically stable single crystal of L-2 and kinetically stable supramolecular aggregates of L-2 were precisely elucidated by cryo-TEM, WAX, SAXS, UV/Vis, IR analyses, and single-crystal X-ray crystallography. An antiparallel β-sheet-type aggregate consisting of an infinite one-dimensional hydrogen-bonding network of amide groups and π-stacking of PdCl(dpb) moieties was observed in the supramolecular gel fiber of L-2, even though discrete dimers are assembled through hydrogen bonding in the thermodynamically stable single crystal of L-2. The disparate DSC profiles of the single crystal and xerogel of L-2 indicate different thermodynamics of the molecular assembly process. Metalated amino acids: A series of NCN-pincer Pd-complex-bound norvaline derivatives was successfully synthesized without loss of the optical purity and Pd unit. Efficient self-assembly properties of these Pd-norvalines were found to afford well-regulated Pd arrays both in the single crystal and in the supramolecular gel. A solvent-dependent configuration control of the Pd array was corroborated by means of single-crystal X-ray crystallography and cryo-TEM analysis. Copyright

1,4-Benzene-bridged covalent hybrid of triarylamine and cyclometalated ruthenium: A new type of organic-inorganic mixed-valent system

Yao, Chang-Jiang,Zheng, Ren-Hui,Shi, Qiang,Zhong, Yu-Wu,Yao, Jiannian

supporting information; experimental part, p. 5680 - 5682 (2012/07/17)

A 1,4-benzene-bridged covalent hybrid of triarylamine and cyclometalated ruthenium 12+ was isolated as a bench-stable open-shell substance. The free spin in this complex is mainly associated with the triarylamine unit, as indicated by EPR and D

CYCLIC AZINE DERIVATIVES, PROCESSES FOR PRODUCING THESE, AND ORGANIC ELECTROLUMINESCENT ELEMENT CONTAINING THESE AS COMPONENT

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Page/Page column 66, (2012/07/03)

A cyclic azine compound represented by general formula (1): wherein each Ar1 represents an aromatic group, which is unsubstituted or substituted by a C1-4 alkyl group, a phenyl group or a pyridyl group; and A represents a group selected from those which are represented by general formulae (2) to (5), described in the description. The cyclic azine compound is useful for an organic compound layer of fluorescent or phosphorescent EL device.

Synthesis of vinyl-substituted polypyridyl ligands through suzuki-miyaura cross-coupling of potassium vinyltrifluoroborate with bromopolypyridines

Nie, Hai-Jing,Yao, Jiannian,Zhong, Yu-Wu

body text, p. 4771 - 4775 (2011/07/08)

Suzuki-Miyauru cross-coupling of bromopolypyridines with potassium vinyltrifluoroborate affords vinyl-substituted polypyridyl ligands in moderate to good yields. This reaction allows simple and practical syntheses of numerous vinyl-substituted polypyridin

Cyclo-ruthenated and -platinated complexes bearing phosphonate substituents

Wadman, Sipke H.,Tooke, Duncan M.,Spek, Anthony L.,van Klink, Gerard P.M.,van Koten, Gerard

experimental part, p. 1701 - 1706 (2010/08/22)

Two new, potentially cyclometalating terdentate ligands bearing phosphonate substituents, Et2O3P-N^C(H)^N (5) and Et2O3P-C(H)^N^N (7), have been prepared. The corresponding ruthenium complexes, [1]+ and [2]+, respectively, were obtained by reaction with [RuCl3(tpy)]. Complexes [1]+ and [2]+ display electronic properties characteristic for cyclometalated ruthenium complexes. The platinum complex [3], of N^C(H)^N ligand 5, was also prepared and is highly phosphorescent in solution. In general, the phosphonate group electronically behaves equivalent to a carboxylate moiety.

An efficient synthesis of versatile terpyridine analogues for cyclometallated luminescent cyclodextrins

Chavarot, Murielle,Pikramenou, Zoe

, p. 6865 - 6868 (2007/10/03)

An efficient synthetic method for preparing functionalised terpyridyl analogues based on Negishi's zinc coupling is developed. These ligands form cyclometallated complexes; attaching them to cyclodextrins allows preparation of luminescent cyclometallated ruthenium cyclodextrins for the assembly of photoactive units via non-covalent interactions.

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