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224448

Sigma-Aldrich

Phenylmagnesium chloride solution

2.0 M in THF

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Synonym(s):
Chlorophenylmagnesium
Linear Formula:
C6H5MgCl
CAS Number:
100-59-4
Molecular Weight:
136.86
Beilstein:
3587900
MDL number:
MFCD00000464
UNSPSC Code:
12352103
PubChem Substance ID:
24853438
NACRES:
NA.22

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

2.0 M in THF

density

~1.02 g/mL at 20 °C
1.042 g/mL at 25 °C

SMILES string

Cl[Mg]c1ccccc1

InChI

1S/C6H5.ClH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1

InChI key

GQONLASZRVFGHI-UHFFFAOYSA-M

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Application

Phenylmagnesium chloride (PhMgCl) solution is a common Grignard reagent used in the synthesis of (−)-phenserine and stephacidin B. It is employed in a variety of cross-coupling reactions. It can also be used as an electrolyte solution along with aluminium chloride (AlCl3) in the rechargeable magnesium batteries.

Packaging

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Other Notes

Storage below 25°C may cause formation of crystalline magnesium salts. Moving container to a warm location and occasional gentle swirling should redissolve the solid

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Nickel-Catalyzed Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents.
B ohm VPW, et al.
Angewandte Chemie (International Edition in English), 39(9), 1602-1604 (2000)
Electrolyte solutions with a wide electrochemical window for rechargeable magnesium batteries.
Mizrahi O, et al.
Journal of the Electrochemical Society, 155(2), A103-A109 (2008)
Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (−)-phenserine
Huang A, et al.
Journal of the American Chemical Society, 126(43), 14043-14053 (2004)
Enantioselective synthesis of stephacidin B.
Herzon S, et al.
Journal of the American Chemical Society, 127(15), 5342-5344 (2005)
Oleg V Larionov et al.
Organic letters, 16(3), 864-867 (2014-01-15)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method
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