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Merck
CN

331376

Phenylmagnesium bromide solution

1.0 M in THF

Synonym(s):

PhMgBr solution

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About This Item

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

Key Documents

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InChI

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

SMILES string

Br[Mg]c1ccccc1

InChI key

ANRQGKOBLBYXFM-UHFFFAOYSA-M

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

1.004 g/mL at 25 °C

Quality Level

200

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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

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000522807
0000522807
0000510553
0000510553
0000498617

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Palladium?Catalyzed Coupling of Alkyl Chlorides and Grignard Reagents.
Frisch A C, et al.
Angewandte Chemie (International Edition in English), 41(21), 4056-4059 (2002)
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)
Ying Li et al.
Analytica chimica acta, 884, 106-113 (2015-06-16)
A novel molecularly imprinted electrochemical sensor based on Fe3O4 nanobeads immobilized on graphene (Fe3O4-MIP@RGO) has been developed for detecting 17β-estradiol (17β-E2) in water using reversible addition fragmentation chain transfer (RAFT) polymerization technique. 17β-E2 can be detected by this electrochemical sensor

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