Skip to Content
Merck
CN

225584

Vinylmagnesium bromide solution

1.0 M in THF

Synonym(s):

Bromoethenylmagnesium, Bromovinylmagnesium

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Linear Formula:
CH2=CHMgBr
CAS Number:
Molecular Weight:
131.25
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3535841
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


Quality Level

reaction suitability

reaction type: Grignard Reaction

packaging

Kilo-Lab® of , Sure/Seal of

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

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.

Other Notes

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

Legal Information

Kilo-Lab is a registered trademark of Merck KGaA, Darmstadt, Germany
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC


Still not finding the right product?

Explore all of our products under Vinylmagnesium bromide solution


signalword

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

Central nervous system, Respiratory system

supp_hazards

Storage Class

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

flash_point_f

1.4 °F

flash_point_c

-17.0 °C

ppe

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

Regulatory Information

危险化学品

This item has



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library



A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine,(?)-pelletierine,(+)-?-coniceine, and (+)-epidihydropinidine.
Takahata H
Tetrahedron Asymmetry, 7(10), 3047-3054 (1996)
Synthesis and structure?activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents.
Albrecht U
Bioorganic & Medicinal Chemistry, 13(5), 1531-1536 (2005)
A useful new enantiomerically pure synthon from malic acid: chelation controlled activation as a route to regioselectivity.
Keck G E
The Journal of Organic Chemistry, 56(1), 417-420 (1991)



Global Trade Item Number

SKUGTIN
225584-18L-KL04061838125729
225584-4X25ML04065268447383
225584-PZ04061823820127
225584-18L-C04061838231130
225584-800ML04061838779571
225584-100ML04061838779557
225584-4X100ML04061838779564