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1-BROMO-2-NITRO-4,5-DI(TRIFLUOROMETHYL)BENZENE - CAS 229957-08-8

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Category
Main Product
Product Name
1-BROMO-2-NITRO-4,5-DI(TRIFLUOROMETHYL)BENZENE
Catalog Number
229957-08-8
Synonyms
1-BROMO-2-NITRO-4,5-DI(TRIFLUOROMETHYL)BENZENE; 4,5-Bis(trifluoromethyl)-2-bromo-1-nitrobenzene
CAS Number
229957-08-8
Molecular Weight
338
Molecular Formula
C8H2BrF6NO2
COA
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MSDS
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Canonical SMILES
C1=C(C(=CC(=C1[N+](=O)[O-])Br)C(F)(F)F)C(F)(F)F
InChI
InChI=1S/C8H2BrF6NO2/c9-5-1-3(7(10,11)12)4(8(13,14)15)2-6(5)16(17)18/h1-2H
InChIKey
JIJNLAOEXTXBRF-UHFFFAOYSA-N
Structure
CAS 229957-08-8 1-BROMO-2-NITRO-4,5-DI(TRIFLUOROMETHYL)BENZENE
Specification
Purity
95%
Boiling Point
230.3ºC at 760 mmHg
Density
1.832g/cm3
Reference Reading
1.One-pot synthesis of symmetric and asymmetric p-quinone ligands and unprecedented substituent induced reactivity in their dinuclear ruthenium complexes.
Schweinfurth D1, Das HS, Weisser F, Bubrin D, Sarkar B. Inorg Chem. 2011 Feb 7;50(3):1150-9. doi: 10.1021/ic101972u. Epub 2011 Jan 7.
The compounds 2-[2-(trifluoromethyl)-anilino]-5-hydroxy-1,4-benzoquinone (L(1)), 2,5-di-[2-(trifluoromethyl)-anilino]-1,4-benzoquinone (L(2)), 2-[2-(methylthio)-anilino]-5-hydroxy-1,4-benzoquinone (L(3)), and 2,5-di-[2-(methylthio)-anilino]-1,4-benzoquinone (L(4)) were prepared in high yields by reacting 2,5-dihydroxy-1,4-benzoquinone with the corresponding amines in a one-pot synthesis in refluxing acetic acid. This straightforward and "green" synthesis delivers biologically relevant asymmetric p-quinones such as L(1) and L(3) in a rare, simple, one-step process. The proposed synthetic route is general and can be applied to generate a variety of such molecules with different substituents on the nitrogen atoms. Structural characterization of L(2) and L(4) shows electron delocalization across the "upper" and "lower" parts of the molecule, thus showing the importance of charge separated species in the proper description of such molecules. Reactions of these ligands with [Cl(η(6)-Cym)Ru(μ-Cl)(2)Ru(η(6)-Cym)Cl] (Cym = p-Cymene = 1-isopropyl-4-methyl-benzene) in the presence of a base result in the formation of complexes [{Cl(η(6)-Cym)Ru}(2)(μ-L(-2H)(1))] (1), [{Cl(η(6)-Cym)Ru}(2)(μ-L(-2H)(2))] (2), [{Cl(η(6)-Cym)Ru}(2)(μ-L(-2H)(3))] (3), and [{Cl(η(6)-Cym)Ru}(2)(μ-L(-2H)(4))] (4).
2.Synthesis and biodistribution of [(11)C]R116301, a promising PET ligand for central NK(1) receptors.
Van der Mey M1, Janssen CG, Janssens FE, Jurzak M, Langlois X, Sommen FM, Verreet B, Windhorst AD, Leysen JE, Herscheid JD. Bioorg Med Chem. 2005 Mar 1;13(5):1579-86.
N1-(2,6-Dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl)[carbonyl-(11)C]benzoyl]hexahydro-4-pyridinyl}piperazino)acetamide ([(11)C]R116301) was prepared and evaluated as a potential positron emission tomography (PET) ligand for investigation of central neurokinin(1) (NK(1)) receptors. 1-Bromo-3,5-di(trifluoromethyl)benzene was converted in three steps into 3,5-di(trifluoromethyl)[carbonyl-(11)C]benzoyl chloride, which was reacted with N1-(2,6-dimethylphenyl)-2-{4-[(2R,4S)-2-benzylhexahydro-4-pyridinyl]piperazino}acetamide providing [(11)C]R116301 in 45-57% decay-corrected radiochemical yield. The total synthesis time, from end of bombardment (EOB) to the formulated product, was 35 min. Specific activity (SA) was 82-172 GBq/micromol (n=10) at the end of synthesis. N1-([4-(3)H]-2,6-Dimethylphenyl)-2-(4-{(2R,4S)-2-benzyl-1-[3,5-di(trifluoromethyl)benzoyl]hexahydro-4-pyridinyl}piperazino)acetamide ([(3)H]R116301) was also synthesized (SA: 467 GBq/mmol).
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