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Sigma-Aldrich

Phenylmagnesium bromide solution

1.0 M in THF

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Synonym(s):
PhMgBr solution
Linear Formula:
C6H5MgBr
CAS Number:
100-58-3
Molecular Weight:
181.31
Beilstein/REAXYS Number:
3588849
MDL number:
MFCD00000038
UNSPSC Code:
12352103
PubChem Substance ID:
24859956
NACRES:
NA.22

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

1.004 g/mL at 25 °C

SMILES string

Br[Mg]c1ccccc1

InChI

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

InChI key

ANRQGKOBLBYXFM-UHFFFAOYSA-M

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Application

Phenylmagnesium bromide (PhMgBr) solution is an organomagnesium reagent mainly used in Grignard reaction, which finds application as the key step in the synthesis of (S)-2(diphenylmethyl)pyrrolidine, a chiral solvating agent for the NMR analysis. PhMgBr can also undergo palladium-catalyzed Grignard coupling with alkyl chlorides to form the cross-coupled product in good yield.

Other Notes

Storage below 25°C may cause crystallization. Warm gently to redissolve solid.

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH014,EUH019

wgk_germany

WGK 3

flash_point_f

1.4 °F

flash_point_c

-17 °C

ppe

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

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’.

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A short synthesis of (S)-2-(diphenylmethyl) pyrrolidine, a chiral solvating agent for NMR analysis.
Bailey D J, et al.
Tetrahedron Asymmetry, 8(1), 149-153 (1997)
Palladium?Catalyzed Coupling of Alkyl Chlorides and Grignard Reagents.
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