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Sigma-Aldrich

1-Phenylpyrazole

97%

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About This Item

Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
1126-00-7
Molecular Weight:
144.17
EC Number:
214-415-1
MDL number:
MFCD00003112
UNSPSC Code:
12352100
PubChem Substance ID:
24856799
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.596 (lit.)

bp

141-142 °C/30 mmHg (lit.)

density

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

InChI key

WITMXBRCQWOZPX-UHFFFAOYSA-N

Related Categories

General description

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.

Application

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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