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224448

Sigma-Aldrich

Phenylmagnesium chloride solution

2.0 M in THF

Synonym(s):

Chlorophenylmagnesium

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About This Item

Linear Formula:
C6H5MgCl
CAS Number:
100-59-4
Molecular Weight:
136.86
Beilstein/REAXYS Number:
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

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Danger

Hazard Classifications

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

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Enantioselective synthesis of stephacidin B.
Herzon S, et al.
Journal of the American Chemical Society, 127(15), 5342-5344 (2005)
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)
Functional group tolerant Kumada- Corriu- Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: Catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents.
Vechorkin O, et al.
Journal of the American Chemical Society, 131(28), 9756-9766 (2009)
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)
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)
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