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1-Phenylpyrazol
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About This Item
Empirische Formel (Hill-System):
C9H8N2
CAS-Nummer:
Molekulargewicht:
144.17
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22
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Qualitätsniveau
Assay
97%
Form
liquid
Brechungsindex
n20/D 1.596 (lit.)
bp
141-142 °C/30 mmHg (lit.)
Dichte
1.091 g/mL at 25 °C (lit.)
SMILES String
c1ccc(cc1)-n2cccn2
InChI
1S/C9H8N2/c1-2-5-9(6-3-1)11-8-4-7-10-11/h1-8H
InChIKey
WITMXBRCQWOZPX-UHFFFAOYSA-N
Allgemeine Beschreibung
1-Phenylpyrazole undergoes cyclometallation with rhodium trichloride to yield rac-di(μ-chloro)tetrakis[2-(pyrazol-1-yl)phenyl-C1,N2′]dirhodium. The activation of the C-H bond of 1-phenylpyrazole autocatalyzed by the co-product HOAc was studied.
Anwendung
1-Phenylpyrazole has been used:
- in the preparation of 4,5-diphenylpyrazolo[1,5-a]quinoline, 1-(1,2,3,4-tetraphenylnaphthalen-5-yl)pyrazole and 1-(1,2,3,4,5,6,7,8-octaphenylanthracen-9-yl)pyrazole
- as cyclometallated ligand in the preparation of new heteroleptic iridium(III) complexes
Signalwort
Warning
H-Sätze
Gefahreneinstufungen
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Zielorgane
Respiratory system
Lagerklassenschlüssel
10 - Combustible liquids
WGK
WGK 3
Flammpunkt (°F)
235.4 °F - closed cup
Flammpunkt (°C)
113 °C - closed cup
Persönliche Schutzausrüstung
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Jian-ning Yu et al.
Guang pu xue yu guang pu fen xi = Guang pu, 30(9), 2424-2427 (2010-11-26)
New heteroleptic iridium(III) complexes (ppz)2Ir(LX), which consist of two cyclometalated ligands ppz(1-phenylpyrazole) together with an ancillary ligand LX (LX= 2-(2'-hydroxylphenyl)benzothiazole (BTZ), 2-(3'-methyl-2'-hydroxylphenyl) benzothiazole (3-MeBTZ), 2-(4'-methyl-2'-hydroxylphenyl) benzothiazole (4-MeBTZ) and 2-(4'-Trifluoromethyl-2'hydroxylphenyl) benzothiazole (4-tfmBTZ)), were synthesized and characterized. The molecular structures and photophysical
Cyclometallated compounds: VII. X-Ray crystal structure of the product of cyclometallation of 1-phenylpyrazole with rhodium trichloride.
Steel PJ.
Journal of Organometallic Chemistry, 408(3), 395-402 (1991)
Indira Fabre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(23), 7595-7604 (2013-04-19)
The activation of the C-H bond of 1-phenylpyrazole (2) and 2-phenyl-2-oxazoline (3) by [Ru(OAc)2(p-cymene)] is an autocatalytic process catalyzed by the co-product HOAc. The reactions are indeed faster in the presence of acetic acid and water but slower in the
Nobuyoshi Umeda et al.
The Journal of organic chemistry, 76(1), 13-24 (2010-12-15)
The direct oxidative coupling of phenylazoles with internal alkynes proceeds efficiently in the presence of a rhodium catalyst and a copper oxidant accompanied by double or quadruple C-H bond cleavages. Thus, as a representative example, 4,5-diphenylpyrazolo[1,5-a]quinoline, 1-(1,2,3,4-tetraphenylnaphthalen-5-yl)pyrazole, and 1-(1,2,3,4,5,6,7,8-octaphenylanthracen-9-yl)pyrazole can
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