23719-80-4

Basic information

• Product Name: Cyclopropylmagnesium bromide
• Synonyms: CYCLOPROPYLMAGNESIUM BROMIDE;CYCLOPROPYLMAGNESIUM BROMIDE, 0.5 M IN THF;Cyclopropylmagnesium Bromide 0.75 M In Tetrahydrofuran;Cyclopropylmagnesium Bromide, 0.5 M in Tetrahydrofuran;cyclopropylmagnesium bromide solution;Cyclopropylmagnesium Bromide (15% in Tetrahydrofuran, ca. 1mol/L);Bromocyclopropylmagnesium;Cyclopropylbromomagnesium
• CAS NO: 23719-80-4
• Molecular Formula: C₃H₅BrMg
• Molecular Weight: 145.28
• EINECS: 472-500-0
• Product Categories: Cyclopropanes;Grignard Reagents;Grignard Reagents & Alkyl Metals;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Alkyl;Grignard Reagents;Organometallic Reagents;25mL Sure/Seal Reagents;Chemical Synthesis;Organometallic Reagents;Grignard Reagent
• Mol File: 23719-80-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 65 °C
• Flash Point: 65°C
• Appearance: Yellow to green/Turbid Liquid
• Density: 0.968 g/mL at 25 °C
• Vapor Pressure: 5350mmHg at 25°C
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water (17 mg/ml), (25°C). Soluble in organic solvents.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: Cyclopropylmagnesium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropylmagnesium bromide(23719-80-4)
• EPA Substance Registry System: Cyclopropylmagnesium bromide(23719-80-4)

Safety Data

• Hazard Codes: F,Xi,C
• Statements: 11-14-19-36/37/38-40-37-34
• Safety Statements: 16-26-45-36/37/39
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 1
• HazardClass: 4.3
• PackingGroup: II
• Hazardous Substances Data: 23719-80-4(Hazardous Substances Data)

Usage

Description

Cyclopropylmagnesium bromide is a clear, colorless solution that is an organometallic compound with the chemical formula C3H5BrMg. It is a Grignard reagent, which is a type of compound that contains a carbon-metal bond and is widely used in organic synthesis.

Uses

Used in Pharmaceutical Industry:
Cyclopropylmagnesium bromide is used as a key reagent for the preparation of aminopropylindenes, which are a chemotype of oxidosqualene cyclase (OSC) inhibitors. These inhibitors play a crucial role in the development of pharmaceuticals targeting various diseases.
Used in Chemical Synthesis:
Cyclopropylmagnesium bromide is used as a reagent in the Grignard reaction, which is an essential step in the synthesis of various organic compounds, including aminopropylindenes. This reaction allows the formation of cyclopropylboronic acid by reacting with trimethylborate, which can then undergo Suzuki-type coupling reactions with different aryl and heteroaryl bromides to form cyclopropyl adducts.
Used in Microbiology:
Cyclopropylmagnesium bromide is used as the starting nutrient mix for dropout studies, where fermentation conditions require the absence of one or more essential amino acids. This application is crucial for classifying yeasts based on their colonial characteristics and cell morphology.

InChI:InChI=1/C3H5.BrH.Mg/c1-2-3-1;;/h1H,2-3H2;1H;/q-1;;+2/p-1

Upstream product

• 60-29-7 diethyl ether 
• 4333-56-6 cyclopropyl bromide 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 

Downstream Products

• 4313-03-5 (2E,4E)-hepta-2,4-dienal 
• 52692-55-4 2-Cyclopropyl-3-phenyl-2-butanol 
• 52692-54-3 1,1-Dicyclopropyl-2,2-diphenyl-ethanol 
• 52692-22-5 2,2-diphenyl-1-cyclopropylethan-1-one 
• 14113-96-3 1,2-dicyclopropylethanone 
• 23719-88-2 tricyclopropylcarbinol 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 123751-93-9 1-((E)-Buta-1,3-dienyl)-4-cyclopropyl-benzene 
• 4165-81-5 1,1-diphenyl-1,3-butadiene 
• 116808-70-9 cyclopropyldiphenylsulfonium triflate 
• 19714-73-9 1-cyclopropyl-3-methylbenzene 
• 6921-43-3 1-cyclopropyl-4-methyl-benzene 
• 27546-46-9 2-methyl-1-cyclopropylbenzene 
• 106872-31-5 methyl 2-(N-benzyloxycarbonylamino)-2-cyclopropylacetate 

Relevant articles and documents

The surface nature of grignard reagent formation: Cyclopropylmagnesium bromide

The reaction of cyclopropyl bromide with managesium in diethyl directly ether yielded directly, during formation of the Grignard reagent, ～25-30% cyclopropane. Also formed in the reaction was ～25% cyclopropylmagnesium bromide. The reaction, when conducted in perdeuterated diethyl in diethyl ether in the presence of the radical trap deuterated dicyclohexylphosphine, showed that the cyclopropane is formed mainly by disproportionation of the cyclopropyl radicals on the magnesium surface (～85%) only a small amount (～15%) by reaction of a "freely radical" with the solvent. The reaction in methanol-O-d yielded almost exclusively 1-deuteriocyclopropane. These provide further experimental evidence that the basic assumption of the D-model "that all radicals leave the surface and diffuse freely in solution" is not valid.

Solvent attack in grignard reagent formation from bromocyclopropane and 1-bromohexane in diethyl ether

In the reaction of magnesium with bromocyclopropane in diethyl ether at reflux, intermediate cyclopropyl radicals attack the solvent, giving cyclopropane (20-30 mol/100 mol of bromocyclopropane consumed) and solvent-derived products. In contrast, the similar reaction of 1-bromohexane gives no more than 0.5 mol of hexane from solvent attack by hexyl radicals. These data are consistent with calculations based on a mechanism (D Model) with freely diffusing intermediate radicals, in which cyclopropyl and hexyl radicals have similar reactivities in their conversions to Grignard reagents, but the cyclopropyl radical is approximately 1000 times as reactive toward the solvent as the hexyl radical.