499803
2-Chlorophenylzinc iodide solution
0.5 M in THF
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About This Item
Linear Formula:
ClC6H4ZnI
CAS Number:
Molecular Weight:
303.84
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/C6H4Cl.HI.Zn/c7-6-4-2-1-3-5-6;;/h1-4H;1H;/q;;+1/p-1
SMILES string
Clc1ccccc1[Zn]I
InChI key
MADDWNUAYOHWRC-UHFFFAOYSA-M
concentration
0.5 M in THF
density
0.973 g/mL at 25 °C
storage temp.
2-8°C
Application
2-Chlorophenylzinc iodide is an organozinc compound, which can be used as a reactant in Negishi cross-coupling reaction to construct carbon-carbon bonds by reacting with organic halides using nickel or palladium catalysts.
It can also be utilized as a reactant to prepare:
It can also be utilized as a reactant to prepare:
- Arylmethanes via rhodium-catalyzed cross-coupling reaction with methyl halides.
- (2-chlorobenzyl)trimethylsilane by Rh-catalyzed cross-coupling reaction with (iodomethyl)trimethylsilane.
- Dichloro biphenyl by palladium catalyzed oxidative homocoupling reaction using N-chlorosuccinimide (NCS) or O2 as the oxidant.
Legal Information
Product of Rieke® Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
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Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
1.0 °F - closed cup
flash_point_c
-17.22 °C - closed cup
Regulatory Information
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Synthesis of functionalized benzylsilanes from arylzinc compounds and (iodomethyl) trimethylsilane by means of a novel Rh catalysis
Takahashi H, et al.
The Journal of Organic Chemistry, 71(2), 671-675 (2006)
Palladium-catalyzed synthesis of biaryls from arylzinc compounds using N-chlorosuccinimide or oxygen as an oxidant
Hossain KM, et al.
Bulletin of the Chemical Society of Japan, 74(12), 2415-2420 (2001)
Novel Rh (I)-Catalyzed reaction of arylzinc compounds with methyl halides
T Kentaro, et al.
Chemistry Letters (Jpn), 1999(11), 1241-1242 (1999)
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao Q, et al.
Angewandte Chemie (International Edition in English), 130(35), 11509-11513 (2018)
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