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732737

Sigma-Aldrich

4-(Benzaldehyde diethylacetal)magnesium bromide solution

1 M in THF

Synonym(s):

4-(Diethoxymethyl)phenylmagnesium bromide

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About This Item

Empirical Formula (Hill Notation):
C11H15BrMgO2
Molecular Weight:
283.44
MDL number:
MFCD11553216
UNSPSC Code:
12352103
PubChem Substance ID:
329764754
NACRES:
NA.22

form

solution

reaction suitability

reaction type: Grignard Reaction

concentration

1 M in THF

density

1.013 g/mL at 25 °C

functional group

ether

SMILES string

CCOC(OCC)c1ccc([Mg]Br)cc1

InChI

1S/C11H15O2.BrH.Mg/c1-3-12-11(13-4-2)10-8-6-5-7-9-10;;/h6-9,11H,3-4H2,1-2H3;1H;/q;;+1/p-1

InChI key

APPJPCOJOCVSMA-UHFFFAOYSA-M

Application

4-(Benzaldehyde diethylacetal)magnesium bromide can be used as a substrate in the sp3 C-H arylation of tetrahydroisoquinolines using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).[1]

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-22.0 °F

flash_point_c

-30 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD9732V
SHBC8126V
03096MMV
03096MM

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Simple and Direct sp3 C-H Bond Arylation of Tetrahydroisoquinolines and Isochromans via 2, 3-Dichloro-5, 6-dicyano-1, 4-benzoquinone Oxidation under Mild Conditions
Muramatsu W, et al.
Organic Letters, 15(14), 3650-3653 (2013)

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