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499803

Sigma-Aldrich

2-Chlorophenylzinc iodide solution

0.5 M in THF

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About This Item

Linear Formula:
ClC6H4ZnI
CAS Number:
148651-35-8
Molecular Weight:
303.84
MDL number:
MFCD01863648
UNSPSC Code:
12352103
PubChem Substance ID:
24873302
NACRES:
NA.22
Pricing and availability is not currently available.

concentration

0.5 M in THF

density

0.973 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Clc1ccccc1[Zn]I

InChI

1S/C6H4Cl.HI.Zn/c7-6-4-2-1-3-5-6;;/h1-4H;1H;/q;;+1/p-1

InChI key

MADDWNUAYOHWRC-UHFFFAOYSA-M

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.[1]
It can also be utilized as a reactant to prepare:
  • Arylmethanes via rhodium-catalyzed cross-coupling reaction with methyl halides.[2]
  • (2-chlorobenzyl)trimethylsilane by Rh-catalyzed cross-coupling reaction with (iodomethyl)trimethylsilane.[3]
  • Dichloro biphenyl by palladium catalyzed oxidative homocoupling reaction using N-chlorosuccinimide (NCS) or O2 as the oxidant.[4]

Legal Information

Product of Rieke® Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.0 °F - closed cup

Flash Point(C)

-17.22 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
03919DE
05020PS

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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)
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)
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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