Cyclopropylzinc bromide, 0.50 M in THF

Base Information

• Chemical Name: Cyclopropylzinc bromide, 0.50 M in THF
• CAS No.: 126403-68-7
• Molecular Formula: C3H5BrZn
• Molecular Weight: 186.35600
• Hs Code.: 29319090
• European Community (EC) Number: 628-622-3
• DSSTox Substance ID: DTXSID601313676
• Mol file: 126403-68-7.mol

Synonyms:126403-68-7;Cyclopropylzinc bromide, 0.50 M in THF;Zinc, bromocyclopropyl-;bromozinc(1+);cyclopropane;MFCD08741505;DTXSID601313676;AKOS016017927;CyclopropylZinc bromide, 0.5M in THF, packaged under Argon in resealable bottles

Chemical Property of Cyclopropylzinc bromide, 0.50 M in THF

Chemical Property:

• Flash Point: -17oC
• PSA: 0.00000
• Density: 0.969 g/mL at 25oC
• LogP: 1.96110
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Miscible with tetrahydrofuran.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 183.88660
• Heavy Atom Count: 5
• Complexity: 14.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclopropylzinc bromide solution 0.5 M in THF ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi,Xn
• Statements: 11-15-19-36/37-40-36/37/38-14
• Safety Statements: 16-26-33-43-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[CH-]1.[Zn+]Br
• General Description: Cyclopropylzinc bromide solution (0.5M in THF or similar solvents) is a stable and highly reactive organometallic reagent widely used in Negishi cross-coupling reactions to introduce cyclopropyl groups into aryl and heteroaryl frameworks. It is efficiently prepared via Rieke zinc activation, exhibits long-term stability, and demonstrates excellent compatibility with diverse functional groups, including ketones, esters, and nitriles. The reagent enables high-yielding, scalable, and copper-free coupling reactions, making it a practical choice for synthesizing functionalized cyclopropanes in both academic and industrial settings.

Refernces

General and user-friendly protocol for the synthesis of functionalized aryl- and heteroaryl-cyclopropanes by Negishi cross-coupling reactions

10.1016/j.tetlet.2009.05.054

The research aims to develop an efficient and scalable method for introducing unsubstituted cyclopropyl moieties into functionalized aryl and heteroaryl compounds through Negishi cross-coupling reactions. The study focuses on using cyclopropylzinc bromide as the organometallic nucleophile, which is prepared via Rieke active zinc technology in a single step with high yields (80–90%) and demonstrated stability over six months. The key chemicals involved include cyclopropylzinc bromide, various aryl halides with sensitive functional groups (such as ketone, methyl ester, ether, nitrile, and nitro groups), and palladium catalysts like Pd(PPh3)4 and PEPPSI. The research concludes that cyclopropylzinc bromide is highly effective in cross-coupling reactions, achieving high yields and fast reaction rates without requiring copper salts as co-catalysts. The protocol is user-friendly, compatible with a broad substrate scope, and suitable for commercial applications due to its scalability and non-pyrophoric nature, making it a valuable advancement in the field of cyclopropane synthesis.