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Sigma-Aldrich

Vinylmagnesium bromide solution

1.0 M in THF

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Synonym(s):
Bromoethenylmagnesium, Bromovinylmagnesium
Linear Formula:
CH2=CHMgBr
CAS Number:
1826-67-1
Molecular Weight:
131.25
Beilstein:
3535841
MDL number:
MFCD00000042
UNSPSC Code:
12352103
PubChem Substance ID:
24853507
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

0.981 g/mL at 25 °C

SMILES string

Br[Mg]C=C

InChI

1S/C2H3.BrH.Mg/c1-2;;/h1H,2H2;1H;/q;;+1/p-1

InChI key

XHHHAXOHMKAOSL-UHFFFAOYSA-M

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Application

Vinylmagnesium bromide solution (1 M in THF) may be used in the synthesis of 2-vinylchroman-4-ones by the conjugate addition with chromones in the presence of a Lewis acid.
It may also be used in the following transformations:
  • (S)-3-(benzyloxy)-4-oxo-butanoic acid methyl ester to methyl (3S,4S)-4-hydroxy-3-(phenylmethoxy)hex-5-enoate.
  • (R)-1-Azido-5,6-epoxyhexane to (S)-1-(4-azidobutyl)-2-propen-1-ol.
  • 2,3-O-Isopropylidene-D-ribose to 1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol.
  • (4S,5S)-2,2-Dimethyl-5-vinyl[1,3]dioxolane-4-carbaldehyde to (1R,4R,5S)- and (1S,4R,5S)-1-(2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)prop-2-en-1-ol.
  • Ethyl levulinate to ?-methyl-?-vinylbutyrolactone.

Packaging

View returnable container options.

Other Notes

Storage below 25°C may cause crystallization. Warm gently to redissolve.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

WGK

WGK 1

Flash Point(F)

1.4 °F

Flash Point(C)

-17.0 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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