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561657

Sigma-Aldrich

(1,3-Dioxan-2-ylethyl)magnesium bromide solution

0.5 M in THF

Synonym(s):

1,3-Dioxane - 2-ethyl- magnesium complex, [2-(1,3-Dioxan-2-yl)ethyl]magnesium bromide

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About This Item

Empirical Formula (Hill Notation):
C6H11BrMgO2
CAS Number:
480438-44-6
Molecular Weight:
219.36
MDL number:
MFCD00061518
UNSPSC Code:
12352103
PubChem Substance ID:
24879959
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.951 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Mg]CCC1OCCCO1

InChI

1S/C6H11O2.BrH.Mg/c1-2-6-7-4-3-5-8-6;;/h6H,1-5H2;1H;/q;;+1/p-1

InChI key

JYNXRXBIEHSSLR-UHFFFAOYSA-M

Related Categories

Application

(1,3-Dioxan-2-ylethyl)magnesium bromide can be used:
  • In a Grignard addition-acylation method for the preparation of enamides.
  • To prepare trisubstituted allenes by reacting with propargylic ammonium salts.
  • In one of the key synthetic steps for the synthesis of febrifugine based antimalarial drugs.

Legal Information

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H319,H335,H351

Precautionary Statements

P261 - P281 - P305 + P351 + P338

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

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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Oxonitriles: A Grignard Addition-Acylation Route to Enamides
Fleming FF, et al.
Organic Letters, 8(21), 4903-4906 (2006)
Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes
Guisan-Ceinos M, et al.
Chemical Communications (Cambridge, England), 54(60), 8343-8346 (2018)
Fraser F Fleming et al.
Organic letters, 8(21), 4903-4906 (2006-10-06)
[reaction: see text] Sequential addition of three different Grignard reagents and pivaloyl chloride to 3-oxo-1-cyclohexene-1-carbonitrile installs four new bonds to generate a diverse array of cyclic enamides. Remarkably, formation of the C-magnesiated nitrile intermediate is followed by preferential acylation by
Exploration of a new type of antimalarial compounds based on febrifugine.
Kikuchi H, et al.
Journal of Medicinal Chemistry, 49(15), 4698-4706 (2006)

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