Skip to Content
Merck
All Photos(1)

Documents

224448

Sigma-Aldrich

Phenylmagnesium chloride solution

2.0 M in THF

Synonym(s):

Chlorophenylmagnesium

Sign Into View Organizational & Contract Pricing


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

Looking for similar products? Visit Product Comparison Guide

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Enantioselective synthesis of stephacidin B.
Herzon S, et al.
Journal of the American Chemical Society, 127(15), 5342-5344 (2005)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service