225584

Vinylmagnesium bromide solution

1.0 M in THF

• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H260,H302,H314,H335,H336,H351
• Precautionary Statements: P210 - P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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