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Specifications
| Appearance: | Gray-black liquid |
| Content: | 0.5 mol in THF |
Transport Information
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Parameter |
Specification |
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UN Number |
3399 |
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Class |
4.3 |
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Packing Group |
II |
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H.S. Code |
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Stability & Reactivity |
The product is chemically stable under standard ambient conditions. |
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Storage |
Tightly closed. Store in a closed, dry, ventilated place |
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Condition to Avoid |
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Package |
Applications
1. Nucleophilic Cyclopropylation
Reacts with electrophiles such as aldehydes, ketones, esters, and acid chlorides to form cyclopropyl-substituted alcohols, ketones, and carboxylic acid derivatives.
Used to introduce cyclopropyl groups, which increase structural rigidity and modify biological activity in drug molecules.
2. Synthesis of Pharmaceuticals and Fine Chemicals
Cyclopropyl groups are often found in CNS-active drugs, antivirals, and enzyme inhibitors. This reagent enables direct introduction of the cyclopropyl moiety into complex molecules.
Employed in the synthesis of cyclopropyl-containing APIs (active pharmaceutical ingredients) such as Efavirenz, Rupatadine, and Vigabatrin intermediates.
3. Cross-Coupling Reactions
Participates in Kumada-type cross-coupling reactions with aryl or vinyl halides under palladium or nickel catalysis to generate aryl-cyclopropyl compounds, which are often biologically active.
4. Organometallic Synthesis
Used to form organometallic intermediates for further functionalization or ring expansion strategies.
Can serve as a starting point for ring-opening reactions under controlled conditions.
Benefits
1. Strained Ring Reactivity
The cyclopropyl ring is highly strained, which can confer unique reactivity patterns useful in complex synthesis and transformation pathways.
2. Efficient C–C Bond Formation
Enables the rapid and selective formation of carbon–carbon bonds with a wide range of electrophiles.
3. Biologically Relevant Functional Group
The cyclopropyl group imparts metabolic stability, lipophilicity, and conformational rigidity, improving drug-like properties of molecules.
4. Compatibility with Modern Catalysis
Well-suited for transition-metal-catalyzed cross-coupling reactions, expanding synthetic flexibility in medicinal chemistry.
5. Modular Building Block
Offers a compact and versatile scaffold that can be functionalized at the ring or appended positions for further chemical elaboration.
Conclusion
Cyclopropylmagnesium bromide (CAS 23719-80-4) is a valuable Grignard reagent for introducing the cyclopropyl group into organic molecules through nucleophilic addition and cross-coupling reactions. It plays a key role in the synthesis of pharmaceutical intermediates, agrochemicals, and specialty materials, offering a balance of chemical reactivity, structural rigidity, and biological relevance. Its use enhances access to complex and functionalized cyclopropyl-containing compounds in modern organic synthesis.
