Description

Allylmagnesium bromide (CAS 1730-25-2) 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 due to its strong basicity and nucleophilicity. It is typically supplied as a solution in diethyl ether or tetrahydrofuran (THF), with concentrations ranging from 0.5M to 2.0M, ensuring optimal handling and reactivity for laboratory applications. Allylmagnesium bromide is particularly valuable for introducing the allyl group (-CH₂CH=CH₂) into organic substrates, enabling the synthesis of complex molecules such as pharmaceuticals, agrochemicals, and specialty materials. Proper storage under inert gas (argon or nitrogen) and refrigeration is essential to maintain its stability and prevent degradation.

This reagent is characterized by its rapid reaction with electrophiles, including carbonyl compounds (aldehydes, ketones, esters), epoxides, and halides, making it indispensable in modern synthetic workflows. Its IUPAC name, magnesium;prop-1-ene;bromide, reflects its structural composition. Researchers should handle Allylmagnesium bromide with caution, using appropriate personal protective equipment (PPE) due to its moisture sensitivity and potential flammability. Each batch is rigorously tested for purity and concentration, ensuring consistent performance in demanding applications.

Properties

• CAS Number: 1730-25-2
• Complexity: 14.4
• IUPAC Name: magnesium;prop-1-ene;bromide
• InChI: InChI=1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q-1;;+2/p-1
• InChI Key: DQEUYIQDSMINEY-UHFFFAOYSA-M
• Exact Mass: 143.94250
• Molecular Formula: C3H5BrMg
• Molecular Weight: 145.28
• SMILES: [CH2-]C=C.[Mg+2].[Br-]
• Monoisotopic Mass: 143.94250
• Physical Description: 10-30% Solution in diethyl ether: Clear light brown liquid;
• Synonyms: Allylmagnesium bromide, 1730-25-2, DTXSID30938266, EINECS 217-046-4, DTXCID101513750, 217-046-4, magnesium;prop-1-ene;bromide, allyl magnesium bromide, allylmagnesiumbromid, allylmagnesiumbromide, allyl magnesiumbromide, allyl-magnesium bromide, 2-propenylmagnesium bromide, Bromo-2-propenyl-magnesium, SCHEMBL1304, 2-propenyl magnesium bromide, SCHEMBL5462827, Bromo(prop-2-en-1-yl)magnesium, FEMBXICCJNZMMC-UHFFFAOYSA-M, MFCD00000044, AKOS015901936, Allylmagnesium bromide 1.0 M in THF, Allylmagnesium bromide, 0.7M in ether, Allylmagnesium bromide 1.0 M in diethyl ether, F0001-0629

Application

Allylmagnesium bromide is primarily used in organic synthesis for the allylation of carbonyl compounds, yielding homoallylic alcohols upon aqueous workup. It serves as a key intermediate in the preparation of fine chemicals, including fragrances, pharmaceuticals, and polymer precursors. The reagent is also employed in cross-coupling reactions and the synthesis of allylic derivatives for material science research. Its versatility makes it a staple in academic and industrial laboratories for constructing carbon-carbon bonds.

Safety and Hazards

GHS Hazard Statements

• H225 (37.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• H250 (60.9%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]
• H260 (63.8%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P210, P222, P223, P231, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 2 (37.7%)
• Pyr. Liq. 1 (60.9%)
• Water-react. 1 (63.8%)
• Skin Corr. 1B (100%)

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