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Safety Information

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:
Molecular Weight:
136.86
Beilstein:
3587900
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

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

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

224448-BULK:
224448-20L:
224448-100ML:4548173118840
224448-18L:4548173118857
224448-VAR:
224448-18L-C:
224448-8L:4548173118871
224448-800ML:4548173118864
224448-PZ:
224448-18L-KL:


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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)
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)
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)

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