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225584 Aldrich

Vinylmagnesium bromide solution

1.0 M in THF

  • CAS Number 1826-67-1

  • Linear Formula CH2=CHMgBr

  • Molecular Weight 131.25

  •  Beilstein Registry Number 3535841

  •  MDL number MFCD00000042

  •  PubChem Substance ID 24853507

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Properties

Related Categories Alkenyl, Chemical Synthesis, Grignard Reagents, Organometallic Reagents
InChI Key   XHHHAXOHMKAOSL-UHFFFAOYSA-M
concentration   1.0 M in THF
density   0.981 g/mL at 25 °C

Description

Other Notes

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

Packaging

100, 4×100, 800 mL in Sure/Seal™

18 L in Kilo-Lab™

View returnable container options.

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.

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides., Reacts violently with water.
RIDADR 
UN 3399BC 4.3(3) / PGII
WGK Germany 
1
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Acids and Bases

Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This Aldrich product line ranges from Brønsted and Lewis...
Chemfiles Volume 1 Article 3

Reagents for C–C Bond Formation

Aldrich carries 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-...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers
15

References

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