19451-11-7

Basic information

• Product Name: Cyclopropyl iodide
• Synonyms: 1-Iodocyclopropane;Cyclopropyl iodide;Iodocyclopropane
• CAS NO: 19451-11-7
• Molecular Formula: C₃H₅I
• Molecular Weight: 167.98
• Mol File: 19451-11-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropyl iodide(19451-11-7)
• EPA Substance Registry System: Cyclopropyl iodide(19451-11-7)

Safety Data

• Hazardous Substances Data: 19451-11-7(Hazardous Substances Data)

Usage

General Description

Cyclopropyl iodide is a chemical compound with the molecular formula C3H5I. It is a colorless to pale yellow liquid that is primarily used as a reagent in organic synthesis. Cyclopropyl iodide is commonly employed in the preparation of various cyclopropyl-substituted compounds, which are valuable intermediates in the pharmaceutical and agrochemical industries. It is also used in the synthesis of complex organic molecules and can act as a halogenating agent in certain reactions. Additionally, it is a valuable building block for the development of new materials and has potential applications in the field of materials science. However, due to its toxic and irritant properties, cyclopropyl iodide should be handled with caution and in accordance with proper safety protocols.

Upstream product

• 1607-29-0 bis((1-methylcyclopropyl)formyl)peroxide 
• 23511-78-6 1,1,3-trichloropropane 
• 4333-56-6 cyclopropyl bromide 

Downstream Products

• 1375405-22-3 C₁₆H₂₀O₄ 
• 35391-85-6 4-cyclopropyl-benzoic acid ethyl ester 
• 6746-94-7 Cyclopropylacetylene 
• 1401797-88-3 N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide 
• 1313028-09-9 ortho-(cyclopropylethynyl)benzoic acid 
• 14633-54-6 cyclopropylphenylsulfide 
• 174484-98-1 3-[Cyclopropyl-(3-nitro-phenyl)-methyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one 

Relevant articles and documents

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Direct Synthesis of Heavy Grignard Reagents: Challenges, Limitations, and Derivatization

The direct synthesis of organocalcium compounds (heavy Grignard reagents) by the reduction of organyl halides with activated calcium powder succeeded in a straightforward manner for organic bromides and iodides that are bound at sp2-hybridized carbon atoms. Extension of this strategy to alkyl halides was very limited, and only the reduction of trialkylsilylmethyl bromides and iodides with activated calcium allowed the isolation of the corresponding heavy Grignard reagents. Substitution of only one hydrogen atom of the methylene moiety by a phenyl or methyl group directed this reduction toward the Wurtz-type coupling and the formation of calcium halide and the corresponding C?C coupling product. The stability of the methylcalcium and benzylcalcium derivatives in ethereal solvents suggests an unexpected reaction behavior of the intermediate organyl halide radical anions. Quantum chemical calculations verify a dependency between the ease of preparative access to organocalcium complexes and the C?I bond lengths of the organyl iodides. The bulkiness of the trialkylsilyl group is of minor importance. Chloromethyltrimethylsilane did not react with activated calcium; however, halogen-exchange reactions allowed the isolation of [Ca(CH2SiMe3)(thf)3(μ-Cl)]2. Furthermore, the metathetical approach of reacting [Ca(CH2SiMe3)I(thf)4] with KN(SiMe3)2 and the addition of N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (pmdeta) allowed the isolation of heteroleptic [CaCH2SiMe3{N(SiMe3)2}(pmdeta)]. In the reaction of this derivative with phenylsilane, the trimethylsilylmethyl group proved to be more reactive than the bis(trimethylsilyl)amido substituent.