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331376

Sigma-Aldrich

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
Beilstein:
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.

Signal Word

Danger

Hazard Statements

H225,H314,H335,H336,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

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 II
2nd 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

331376-VAR-9:
331376-PZ:
331376-100ML:4548173136066
331376-800ML:4548173136073
331376-BULK:
331376-50ML:4548173295626
331376-108L:
331376-BULK-9:
331376-VAR:
331376-4X25ML:

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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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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