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213993

Sigma-Aldrich

4-Iodopyrazole

99%

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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

Quality Level

Assay

99%

form

solid

mp

108-110 °C (lit.)

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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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