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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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Robert E Berry et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 9(2), 135-144 (2003-12-16)
Previously, we utilized 4-iodopyrazole (4IPzH) as a heavy atom derivative for the initial solution of the crystal structure of the nitrophorin from Rhodnius prolixus, NP1, where it was found to bind to the heme with the iodo group disordered in
Hsuan-Liang Liu et al.
Journal of biomedical science, 10(3), 302-312 (2003-04-25)
Molecular docking simulations were performed in this study to investigate the importance of both structural and catalytic zinc ions in the human alcohol dehydrogenase beta(2)beta(2) on substrate binding. The structural zinc ion is not only important in maintaining the structural
A Kojo et al.
Archives of toxicology, 72(6), 336-341 (1998-07-10)
Mouse liver CYP2A5 is induced by several structurally unrelated compounds. In intact mouse liver, pyrazole (PYR) and 4-hydroxypyrazole (4-OH) induce selectively the expression of CYP2A5 while expression of other CYPs is decreased. In this study we exposed mouse primary hepatocytes
Green iodination of pyrazoles with iodine/hydrogen peroxide in water.
Kim MM, et al.
Tetrahedron Letters, 49(25), 4026-4028 (2008)
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
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