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P33402 Aldrich

2-Phenylpyridine Green Alternative

98%

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Properties

Related Categories Building Blocks, C11, Chemical Synthesis, Greener Alternative Products, Heterocyclic Building Blocks,
assay   98%
greener alternative product score   old score: 2
new score: 1
greener alternative product characteristics   Design for Energy Efficiency
Use of Renewable Feedstocks
Inherently Safer Chemistry for Accident Prevention
refractive index   n20/D 1.623(lit.)
bp   268-270 °C(lit.)
density   1.086 g/mL at 25 °C(lit.)
greener alternative category   Re-engineered

Description

Packaging

10, 50 g in glass bottle

Application

Versatile synthetic intermediate.1

Price and Availability


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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
WGK Germany 
3
RTECS 
UT7140900
Flash Point(F) 
230 °F
Flash Point(C) 
110 °C

Protocols & Articles

Peer-Reviewed Papers

References

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1. Aldrichimica Acta 14, 13, (1981)

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides. Larionov OV, Stephens D, Mfuh A, et al. Org. Lett. 16(3), 864-7, (2014)

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Palladium-catalyzed methylation of aryl C-H bond by using peroxides. Zhang Y, Feng J, and Li CJ J. Am. Chem. Soc. 130(10), 2900-1, (2008)

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Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature. Kuninobu Y, Iwanaga T, Omura T, et al. Angew. Chem. Int. Ed. Engl. 52(16), 4431-4, (2013)

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Cobalt-catalyzed hydroarylation of alkynes through chelation-assisted C-H bond activation. Gao K, Lee PS, Fujita T, et al. J. Am. Chem. Soc. 132(35), 12249-51, (2010)

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Peptide-functionalized luminescent iridium complexes for lifetime imaging of CXCR4 expression. Kuil J, Steunenberg P, Chin PT, et al. ChemBioChem. 12(12), 1897-903, (2011)

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Highly self-organized electron transfer from an iridium complex to p-benzoquinone due to formation of a pi-dimer radical anion complex triply bridged by scandium ions. Yuasa J, Suenobu T, and Fukuzumi S J. Am. Chem. Soc. 125(40), 12090-1, (2003)

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Mononuclear platinum(II) complex with 2-phenylpyridine ligands showing high cytotoxicity against mouse sarcoma 180 cells acquiring high cisplatin resistance. Okada T, El-Mehasseb IM, Kodaka M, et al. J. Med. Chem. 44(26), 4661-7, (2001)

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Platinum(II) complexes with dipyridophenazine ligands as human telomerase inhibitors and luminescent probes for G-quadruplex DNA. Ma DL, Che CM, and Yan SC J. Am. Chem. Soc. 131(5), 1835-46, (2009)

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Copper-catalyzed amidation of 2-phenylpyridine with oxygen as the terminal oxidant. John A and Nicholas KM J. Org. Chem. 76(10), 4158-62, (2011)

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A cyclometalated iridium(III) complex with enhanced phosphorescence emission in the solid state (EPESS): synthesis, characterization and its application in bioimaging. Wu H, Yang T, Zhao Q, et al. Dalton Trans. 40(9), 1969-76, (2011)

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Ruthenium-catalyzed meta sulfonation of 2-phenylpyridines. Saidi O, Marafie J, Ledger AE, et al. J. Am. Chem. Soc. 133(48), 19298-301, (2011)

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Ultrafast photodriven intramolecular electron transfer from an iridium-based water-oxidation catalyst to perylene diimide derivatives. Vagnini MT, Smeigh AL, Blakemore JD, et al. Proc. Natl. Acad. Sci. U. S. A. 109(39), 15651-6, (2012)

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Improved high-brightness efficiency of phosphorescent organic LEDs comprising emitter molecules with small permanent dipole moments. Reineke S, Rosenow TC, Lüssem B, et al. Adv. Mater. 22(29), 3189-93, (2010)

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Synthesis and antiproliferative activity of a C,N-cycloplatinated(II) complex with a potentially intercalative anthraquinone pendant. Ruiz J, Vicente C, de Haro C, et al. Inorg. Chem. 50(6), 2151-8, (2011)

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The synthesis and photophysics of tris-heteroleptic cyclometalated iridium complexes. Edkins RM, Wriglesworth A, Fucke K, et al. Dalton Trans. 40(38), 9672-8, (2011)

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An investigation on the second order nonlinear optical response of tris-cyclometallated Ir(III) complexes with variously substituted 2-phenylpyridines. Zaarour M, Guerchais V, Le Bozec H, et al. Dalton Trans. 42(1), 155-9, (2013)

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Platinum (II) complex with cyclometalating 2-phenylpyridine ligand showing high cytotoxicity against cisplatin-resistant cell. El-Mehasseb IM, Kodaka M, Okada T, et al. J. Inorg. Biochem. 84(1-2), 157-8, (2001)

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Easy access to bio-inspired osmium(II) complexes through electrophilic intramolecular C(sp2)-H bond cyclometalation. Cerón-Camacho R, Morales-Morales D, Hernandez S, et al. Inorg. Chem. 47(11), 4988-95, (2008)

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A metal-based inhibitor of NEDD8-activating enzyme. Zhong HJ, Yang H, Chan DS, et al. PLoS ONE 7(11), e49574, (2012)

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1H, 13C, 15N and 195Pt NMR studies of Au(III) and Pt(II) chloride organometallics with 2-phenylpyridine. Pazderski L, Pawlak T, Sitkowski J, et al. Magn. Reson. Chem. 47(11), 932-41, (2009)

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Direct ortho-arylation of N-phenacylpyridinium bromide by palladium-catalyzed C-H-bond activation. Xu J, Cheng G, Su D, et al. Chemistry 15(47), 13105-10, (2009)

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Guest induced morphological transformation from nanospheres to nanowires by hydrogen bond self-assembly. Qin L, Yang H, Qin C, et al. Dalton Trans. 42(14), 4790-4, (2013)

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Calix[6]arene derivatives selectively functionalized at alternate sites on the smaller rim with 2-phenylpyridine and 2-fluorenylpyridine substituents to provide deep cavities. Zeng X, Batsanov AS, and Bryce MR J. Org. Chem. 71(26), 9589-94, (2006)

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PROPHIS: parabolic trough-facility for organic photochemical syntheses in sunlight. Jung C, Funken KH, and Ortner J Photochem. Photobiol. Sci. 4(5), 409-11, (2005)

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Coordination and bond activation in complexes of regioisomeric phenylpyridines with the nickel(II) chloride cation in the gas phase. Tsybizova A, Rulíšek L, Schröder D, et al. J. Phys. Chem. A 117(6), 1171-80, (2013)

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Tuning electronic structure and photophysical properties of [Ir(ppy)₂(py)₂]+ by substituents binding in pyridyl ligand: a computational study. Zhang TT, Qi XX, Jia J, et al. J. Mol. Model. 18(10), 4615-24, (2012)

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Hybridization vs. bond stretching isomerism in Ru(II) cyclometalated complexes of 2-phenylpyridine. Molina B, Alexandrova L, Lelagadec R, et al. Molecules 17(1), 34-47, (2011)

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Beil. 20,V,7,545

Aldrich MSDS 1, 1480:B / Corp MSDS 1 (2), 2796:D / FT-IR 1 (2), 734:C / FT-IR 2 (3), 3707:C / FT-NMR 1 (3), 243:B / IR-Spectra (2), 1139:G / IR-Spectra (3), 1308:D / NMR-Reference 2 (2), 615:A / RegBook 1 (2), 2495:J / Structure Index 1, 394:E:1 / Vapor Phase 3, 1516:A

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