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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:
1730-25-2
Molecular Weight:
145.28
Beilstein/REAXYS Number:
969335
MDL number:
MFCD00000044
UNSPSC Code:
12352103
PubChem Substance ID:
24853518
NACRES:
NA.22

Quality Level

100

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

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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

Packaging

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Danger

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

supp_hazards

EUH019

Storage Class

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

wgk_germany

WGK 1

flash_point_f

-40.0 °F - closed cup

flash_point_c

-40 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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An Efficient Asymmetric Synthesis of Tarchonanthuslactone1.
Reddy M, et al.
The Journal of Organic Chemistry, 66(7), 2512-2514 (2001)
Stereoselective synthesis of the antifungal antibiotic (+)-preussin.
Veeresa G, et al.
Tetrahedron, 54(51), 15673-15678 (1998)
Synthesis of 2-(9, 10-dihydro-9, 10-propanoanthracen-9-yl)-N-methylethanamine via a [4+ 2] cycloaddition.
Karama U, et al.
Molecules (Basel), 15(6), 4201-4206 (2010)
Allylmagnesium Bromide as a selective nucleophile toward Aza-aromatic heterocycles
Henry G et al.
Journal of the American Chemical Society, 79, 1245-1249 (1957)
Synthesis of trihydroxy quinolizidine alkaloids: 1, 3-addition reaction of allylmagnesium bromide to a sugar nitrone.
Dhavale DD, et al.
Tetrahedron, 60(13), 3009-3016 (2004)

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