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470260

Sigma-Aldrich

4-Methoxyphenylmagnesium bromide solution

0.5 M in THF

Synonym(s):

(4-Methoxyphenyl)magnesium bromide, 4-Anisylmagnesium bromide, p-Methoxyphenylmagnesium bromide, Bromo(4-methoxyphenyl)magnesium

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About This Item

Linear Formula:
CH3OC6H4MgBr
CAS Number:
13139-86-1
Molecular Weight:
211.34
MDL number:
MFCD00013515
UNSPSC Code:
12352103
PubChem Substance ID:
24870649
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65-67 °C

density

0.955 g/mL at 25 °C

SMILES string

COc1ccc([Mg]Br)cc1

InChI

1S/C7H7O.BrH.Mg/c1-8-7-5-3-2-4-6-7;;/h3-6H,1H3;1H;/q;;+1/p-1

InChI key

JKXAZEXIOPFJSC-UHFFFAOYSA-M

Application

4-Methoxyphenylmagnesium bromide is a general Grignard reagent that can be used:
  • In the denickelation of porphyrins and to replace the metal center with magnesium.
  • To synthesize a tubulin polymerization inhibitor, 2-Amino-3,4,5-trimethoxybenzophenone.
  • In the total synthesis of (−)-centrolobine.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-4.0 °F

flash_point_c

-20 °C

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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Two successive one-pot reactions leading to the expeditious synthesis of (−)-centrolobine.
Boulard L, et al.
Tetrahedron Letters, 45(35), 6603-6605 (2004)
Demetalation of Metal Porphyrins via Magnesium Porphyrins by Reaction with Grignard Reagents.
Murakami K, et al.
Chemistry?A European Journal , 19(28), 9123-9126 (2013)
2?Amino?3, 4, 5?Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors.
Chuang H Y, et al.
ChemMedChem, 6(3), 450-456 (2011)
Ryosuke Koyama et al.
Bioorganic & medicinal chemistry, 28(11), 115492-115492 (2020-04-16)
Effective chemotherapy for solid cancers is challenging due to a limitation in permeation that prevents anticancer drugs from reaching the center of the tumor, therefore unable to limit cancer cell growth. To circumvent this issue, we planned to apply the

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