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328820

Sigma-Aldrich

4-Fluorophenylmagnesium bromide solution

1.0 M in THF

Synonym(s):

p-Fluorophenylmagnesium bromide, Bromo(4-fluorophenyl)magnesium, Bromo(p-fluorophenyl)magnesium

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About This Item

Linear Formula:
FC6H4MgBr
CAS Number:
352-13-6
Molecular Weight:
199.30
Beilstein:
636802
MDL number:
MFCD00009667
UNSPSC Code:
12352103
PubChem Substance ID:
24859751
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

1.021 g/mL at 25 °C

SMILES string

Fc1ccc([Mg]Br)cc1

InChI

1S/C6H4F.BrH.Mg/c7-6-4-2-1-3-5-6;;/h2-5H;1H;/q;;+1/p-1

InChI key

QYBFFRXNNFXREA-UHFFFAOYSA-M

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Application

4-Fluorophenylmagnesium bromide solution (Grignard reagent) can be used as a reagent in the synthesis of:
  • Useful key intermediate in the synthesis of paroxetine.
  • Arylsulfides via cross-coupling reaction with thiols.
  • 4-Arylmethyl-1-phenylpyrazole and 4-aryloxy-1-phenylpyrazole derivatives as androgen receptor antagonists.
  • Grignard intermediate for preparing aprepitant.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - 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)

-4.0 °F - closed cup

Flash Point(C)

-20 °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’.

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Enantioselective synthesis of 3-substituted-4-aryl piperidines useful for the preparation of paroxetine
Murthy KS K, et al.
Tetrahedron Letters, 44(28), 5355-5358 (2003)
Design, synthesis, and biological evaluation of 4-arylmethyl-1-phenylpyrazole and 4-aryloxy-1-phenylpyrazole derivatives as novel androgen receptor antagonists
Yamamoto S, et al.
Bioorganic & Medicinal Chemistry, 20(7), 2338-2352 (2012)
Understanding the origin of unusual stepwise hydrogenation kinetics in the synthesis of the 3-(4-fluorophenyl) morpholine moiety of NK1 receptor antagonist aprepitant
Brands KMJ, et al.
Organic Process Research & Development, 10(1), 109-117 (2006)
Jun-Hao Cheng et al.
The Journal of organic chemistry, 77(22), 10369-10374 (2012-10-17)
A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were
R A Milius et al.
Journal of medicinal chemistry, 34(5), 1728-1731 (1991-05-01)
The synthesis and pharmacological characterization of a series of N-substituted 3-(4-fluorophenyl)tropane derivatives is reported. The compounds displayed binding characteristics that paralleled those of cocaine, and several had substantially higher affinity at cocaine recognition sites. Conjugate addition of 4-fluorophenyl magnesium bromide
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