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About This Item
Empirical Formula (Hill Notation):
C3H3IN2
CAS Number:
Molecular Weight:
193.97
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
99%
form
solid
mp
108-110 °C (lit.)
functional group
iodo
SMILES string
Ic1cn[nH]c1
InChI
1S/C3H3IN2/c4-3-1-5-6-2-3/h1-2H,(H,5,6)
InChI key
LLNQWPTUJJYTTE-UHFFFAOYSA-N
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General description
4-Iodopyrazole is a valuable intermediate for the synthesis of biologically active compounds. It undergoes iodination in the presence of iodine and ammonium hydroxide to yield 3,4-di-iodo- and 3,4,5-tri-iodo-pyrazole.
Application
4-Iodopyrazole was used in an indium-mediated synthesis of heterobiaryls.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Metin Zora et al.
The Journal of organic chemistry, 76(16), 6726-6742 (2011-07-12)
Electrophilic cyclizations of α,β-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. α,β-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium
A Kojo et al.
Biochemical pharmacology, 42(9), 1751-1759 (1991-10-09)
Pyrazole and several of its derivatives increase the hepatic microsomal coumarin 7-hydroxylase to a variable extent. The strongest inducers are pyrazole itself and those derivatives which have a hydroxy group or a halogen at the 4-position of the molecule. The
Green iodination of pyrazoles with iodine/hydrogen peroxide in water.
Kim MM, et al.
Tetrahedron Letters, 49(25), 4026-4028 (2008)
Enrique Font-Sanchis et al.
The Journal of organic chemistry, 72(9), 3589-3591 (2007-04-05)
The palladium-mediated coupling reaction between triorganoindium reagents and organic electrophiles is extended to the synthesis of heteroaromatic compounds. Both electron-rich and electron-poor heterocycles can act as the organic electrophile or as the organoindium derivative.
Some iodinated pyrazole derivatives.
D Giles et al.
Journal of the Chemical Society. Perkin transactions 1, 13, 1179-1184 (1966-01-01)
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