Description

Bromocyclopropylmagnesium (CAS No. 23719-80-4) is a highly reactive Grignard reagent with the molecular formula C₃H₅BrMg. This organomagnesium compound is widely utilized in organic synthesis for the introduction of the cyclopropyl group into target molecules. 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 moisture and air sensitivity. With a purity typically ranging from 0.5M to 1.0M in solution, this reagent is ideal for nucleophilic addition reactions, cross-coupling processes, and the construction of complex cyclic frameworks. Suitable for researchers and industrial chemists, Bromocyclopropylmagnesium is rigorously quality-controlled to ensure consistency in synthetic applications.

Properties

• CAS Number: 23719-80-4
• Complexity: 14.4
• IUPAC Name: magnesium;cyclopropane;bromide
• InChI: InChI=1S/C3H5.BrH.Mg/c1-2-3-1;;/h1H,2-3H2;1H;/q-1;;+2/p-1
• InChI Key: VFZXMEQGIIWBFJ-UHFFFAOYSA-M
• Exact Mass: 143.94250
• Molecular Formula: C3H5BrMg
• Molecular Weight: 145.28
• SMILES: C1C[CH-]1.[Mg+2].[Br-]
• Monoisotopic Mass: 143.94250
• Synonyms: Cyclopropylmagnesium Bromide, Bromocyclopropylmagnesium, 472-500-0, 607-262-0, 23719-80-4, magnesium;cyclopropane;bromide, CYCLOPROPYL MAGNESIUM BROMIDE, MFCD00672094, Magnesium, bromocyclopropyl-, cyclopropylmagnesiumbromide, bromo(cyclopropyl)magnesium, magnesium,cyclopropane,bromide, cPrMgBr, cyclopropyl magnesiumbromide, bromo-(cyclopropyl)magnesium, cyclopropylmagnesiunn bromide, cyclopropyl-magnesium bromide, SCHEMBL12001, QUPLLJGAJVXXBW-UHFFFAOYSA-M, AKOS015904151, Cyclopropylmagnesium bromide, 0.5M THF, Cyclopropylmagnesium bromide, 1M in THF, DB-369983, C2039, Cyclopropylmagnesium bromide, 0.5M 2-MeTHF, Cyclopropylmagnesium bromide, 0.5M in MeTHF, Cyclopropylmagnesium bromide, 1.0 M in THF, Cyclopropylmagnesium bromide, 0.50 M in THF, Cyclopropylmagnesium bromide, 0.5M-0.7M in THF, Cyclopropylmagnesium bromide (ca. 10% in Tetrahydrofuran, ca. 0.7mol/L)

Application

Bromocyclopropylmagnesium is primarily used in organic synthesis as a key intermediate for the formation of cyclopropane-containing compounds. It participates in nucleophilic addition reactions with carbonyl groups (aldehydes, ketones, esters) to yield cyclopropyl alcohols or derivatives. The reagent is also valuable in transition-metal-catalyzed cross-coupling reactions (e.g., Kumada coupling) for C-C bond formation. Additionally, it serves in the preparation of pharmaceuticals, agrochemicals, and specialty materials requiring cyclopropane motifs.

Safety and Hazards

GHS Hazard Statements

• H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• 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

• P210, P223, 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 (17.1%)
• Pyr. Liq. 1 (59.4%)
• Water-react. 1 (74.9%)
• Water-react. 2 (24.6%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (60.6%)

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