Skip to Content
Merck
All Photos(3)

Documents

225584

Sigma-Aldrich

Vinylmagnesium bromide solution

1.0 M in THF

Synonym(s):

Bromoethenylmagnesium, Bromovinylmagnesium

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

Looking for similar products? Visit Product Comparison Guide

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

Storage Class Code

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

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’.

Already Own This Product?

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

Visit the Document Library

A new endogenous natriuretic factor: LLU-alpha.
Wechter W J
Proceedings of the National Academy of Sciences of the USA, 93(12), 6002-6007 (1996)
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)
Improved and alternative synthesis of D-and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides.
Moon H R
Tetrahedron Asymmetry, 13(11), 1189-1193 (2002)
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)
View All Related Papers

Articles

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service