Description

Bromo(1-methylpropyl)magnesium (CAS No. 922-66-7) is a highly reactive Grignard reagent with the molecular formula C₄H₉BrMg. This organomagnesium compound is widely utilized in synthetic organic chemistry for nucleophilic addition reactions, enabling the formation of carbon-carbon bonds. Supplied as a solution in common solvents such as diethyl ether or tetrahydrofuran (THF), it offers exceptional purity and consistency, making it ideal for laboratory-scale and industrial applications. Its IUPAC name, magnesium;butane;bromide, reflects its structural composition. Proper handling under inert atmospheres (e.g., nitrogen or argon) is essential due to its air- and moisture-sensitive nature. This reagent is a critical tool for researchers in pharmaceuticals, agrochemicals, and advanced material synthesis.

Properties

• CAS Number: 922-66-7
• Complexity: 11.5
• IUPAC Name: magnesium;butane;bromide
• InChI: InChI=1S/C4H9.BrH.Mg/c1-3-4-2;;/h3H,4H2,1-2H3;1H;/q-1;;+2/p-1
• InChI Key: WSHFRLGXCNEKRX-UHFFFAOYSA-M
• Exact Mass: 159.97380
• Molecular Formula: C4H9BrMg
• Molecular Weight: 161.32
• SMILES: CC[CH-]C.[Mg+2].[Br-]
• Monoisotopic Mass: 159.97380
• Synonyms: 922-66-7, Bromo(1-methylpropyl)magnesium, EINECS 213-081-4, 213-081-4, sec-Butylmagnesium Bromide, s-bumgbr, 2-butylmagnesium bromide, sec-Butylmagnesium bromide, 1.0 M in THF, 2-butyl-magnesium bromide, sec-butyl magnesium bromide, bromo(butan-2-yl)magnesium, SCHEMBL113027, JKRPRAXNRSMTPH-UHFFFAOYSA-M, MFCD01321135, DB-256065, NS00079655, EN300-7573077, sec-Butylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L), sec-Butylmagnesium Bromide (ca. 16% in Tetrahydrofuran, ca. 1mol/L)

Application

Bromo(1-methylpropyl)magnesium is primarily used as a Grignard reagent in organic synthesis for the formation of carbon-carbon bonds. It is instrumental in the preparation of tertiary alcohols, ketones, and carboxylic acids through nucleophilic addition reactions. Researchers also employ it in the synthesis of complex organic molecules, including pharmaceuticals and fine chemicals. Its reactivity makes it valuable for alkylation and arylation processes. Strict anhydrous conditions are required to maintain its stability and efficacy.

Safety and Hazards

GHS Hazard Statements

• H260 (100%): 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

• P223, P231+P232, P260, P264, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P405, and P501

Hazard Classes and Categories

• Water-react. 1 (100%)
• Skin Corr. 1B (100%)

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