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225754

Sigma-Aldrich

Allylmagnesium bromide solution

1.0 M in diethyl ether

Synonym(s):

(Prop-2-en-1-yl)magnesium bromide, 2-Propenylmagnesium bromide, Allyl magnesium bromide, Allylbromomagnesium, Allylmagnesiumbromide, Bromo-2-propenylmagnesium

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About This Item

Linear Formula:
CH2=CHCH2MgBr
CAS Number:
Molecular Weight:
145.28
Beilstein:
969335
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in diethyl ether

density

0.851 g/mL at 25 °C

SMILES string

Br[Mg]CC=C

InChI

1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1

InChI key

FEMBXICCJNZMMC-UHFFFAOYSA-M

General description

Allylmagnesium bromide solution serves as a selective nucleophile toward aza-aromatic heterocycles.

Application

Allylmagnesium bromide solution can be used in the Grignard reaction, which is a key step to synthesize:
  • 2-(9,10-dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine (2), a homolog of benzoctamine
  • tarchonanthuslactone
  • (+)-preussin
  • polyhydroxylated quinolizidine alkaloids



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Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 1

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves


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