Description

Magnesium, bromo(1-methylethenyl)- (CAS No. 13291-18-4), also known as Isopropenylmagnesium bromide, is a highly reactive Grignard reagent with the molecular formula C₃H₅BrMg. This organomagnesium compound is widely utilized in synthetic organic chemistry for nucleophilic addition reactions, particularly in the formation of carbon-carbon bonds. Supplied as a solution in common solvents such as diethyl ether or tetrahydrofuran (THF), it is essential to handle under inert conditions (e.g., nitrogen or argon atmosphere) due to its sensitivity to moisture and air. Ideal for researchers and industrial chemists, this reagent is rigorously tested for purity and consistency, ensuring optimal performance in complex synthetic pathways.

Properties

• CAS Number: 13291-18-4
• Complexity: 14.4
• IUPAC Name: magnesium;prop-1-ene;bromide
• InChI: InChI=1S/C3H5.BrH.Mg/c1-3-2;;/h1H2,2H3;1H;/q-1;;+2/p-1
• InChI Key: UZNGRHDUJIVHQT-UHFFFAOYSA-M
• Exact Mass: 143.94250
• Molecular Formula: C3H5BrMg
• Molecular Weight: 145.28
• SMILES: C[C-]=C.[Mg+2].[Br-]
• Monoisotopic Mass: 143.94250
• Synonyms: 13291-18-4, Magnesium, bromo(1-methylethenyl)-, 603-688-6, Isopropenylmagnesium bromide, Isopropenyl magnesium bromide, Magnesium, bromo(1-methylethenyl)- (9CI), bromo(isopropenyl)magnesium, SCHEMBL5957, 2-propen-2-ylmagnesium bromide, prop-1-en-2-ylmagnesium bromide, LFTYALBVGVNGLI-UHFFFAOYSA-M, MFCD00192240, AKOS009156578, Isopropenylmagnesium bromide, 0.5M in THF, Isopropenylmagnesium bromide, 0.50 M in THF, Isopropenylmagnesium bromide, 1.5M in 2-MeTHF

Application

Isopropenylmagnesium bromide is a versatile Grignard reagent used in organic synthesis for the introduction of the isopropenyl group into target molecules. It is commonly employed in nucleophilic additions to carbonyl compounds, such as ketones and aldehydes, to form tertiary alcohols or alkenes. This reagent is also valuable in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals requiring carbon-chain elongation or functional group transformations.

Safety and Hazards

GHS Hazard Statements

• H225 (44.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• H228 (53.9%): Flammable solid [Danger Flammable solids]
• H260 (98.7%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]
• H302 (10.5%): Harmful if swallowed [Warning Acute toxicity, oral]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (11.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P210, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P402+P404, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 2 (44.7%)
• Flam. Sol. 2 (53.9%)
• Water-react. 1 (98.7%)
• Acute Tox. 4 (10.5%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (11.8%)

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