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Sigma-Aldrich

3-Fluorophenylmagnesium bromide solution

0.5 M in THF

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About This Item

Linear Formula:
FC6H4MgBr
CAS Number:
17318-03-5
Molecular Weight:
199.30
MDL number:
MFCD00672007
UNSPSC Code:
12352103
PubChem Substance ID:
24879960
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.936 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Fc1cccc([Mg]Br)c1

InChI

1S/C6H4F.BrH.Mg/c7-6-4-2-1-3-5-6;;/h1-2,4-5H;1H;/q;;+1/p-1

InChI key

VFPDAAQAKDGSHQ-UHFFFAOYSA-M

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Application

3-Fluorophenylmagnesium bromide is a Grignard reagent that can be used in:
  • The preparation of 4-substituted quinazolines by reacting with 2-methylaminobenzonitriles.
  • The synthesis of radiolabeled TrkB/C-targeting kinase inhibitor for positron emission tomography (PET) imaging applications.
  • Cu-catalyzed carbometalation of substituted cyclopropenes.

Legal Information

Product of Rieke® Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Statements

H225,H302,H314,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - 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 1

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’.

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Synthesis of quinazolines via an iron-catalyzed oxidative amination of N-H ketimines
Chen C, et al.
The Journal of Organic Chemistry, 83(4), 2395-2401 (2018)
A kinome-wide selective radiolabeled TrkB/C inhibitor for in vitro and in vivo neuroimaging: synthesis, preclinical evaluation, and first-in-human
Bernard-Gauthier V, et al.
Journal of medicinal chemistry, 60(16), 6897-6910 (2017)
Facially selective and regioselective carbometalation of cyclopropenes by aryl Grignard reagents
Yan N, et al.
The Journal of Organic Chemistry, 73(2), 563-568 (2008)

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