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Here's a concise overview of 3-Cyclopentylacrylonitrile (≤100 words):
Chemical Identity
Formula: C₈H₁₁N
Structure: Unsaturated nitrile with cyclopentyl at C3:
N≡C−CH=CH−C₅H₉
Exists as E/Z isomers (trans preferred).
Key Properties
Liquid (colorless to yellow)
Reactive Sites:
Nitrile (-C≡N)
Activated alkene (Michael acceptor)
Insoluble in water; soluble in ethanol/DCM.
Primary Uses
Pharma Intermediate: Synthesize cyclopentyl-containing drugs (e.g., antivirals, kinase inhibitors).
Agrochemicals: Building block for lipophilic pesticides.
Polymer Modifier: Enhance nitrile rubber properties.
Handling
Toxic/Irritant: Use gloves & fume hood.
Storage: Cold (2–8°C), inert gas to prevent polymerization.
Suppliers: TCI Chemicals, Combi-Blocks.
3-Cyclopentylacrylonitrile (CAS 53684-49-6) is a specialty organic compound with the following key characteristics:
Molecular Formula: C₈H₁₁N
Structure:
Acrylonitrile backbone (CH₂=CH-C≡N)
Cyclopentyl group attached to the β-carbon (C3 position):
N≡C-CH=CH-C₅H₉
↑
Cyclopentyl substituent
Exists as E/Z isomers (trans/cis configuration around C=C bond).
| Property | Description |
|---|---|
| Appearance | Colorless to pale yellow liquid |
| Boiling Point | ~90–95°C (1 mmHg) |
| Solubility | Organic solvents (ethanol, DCM); insoluble in water |
| Reactivity | α,β-Unsaturated nitrile: Undergoes Michael additions, hydrogenation, cycloadditions |
Typically prepared via:
Knoevenagel Condensation:
Cyclopentanecarbaldehyde + Cyanoacetic acid → Dehydration
Cross-Coupling:
Cyclopentylmagnesium bromide + 3-Bromopropenenitrile
Pharmaceutical Intermediates:
Building block for cyclopentane-containing drugs (e.g., antiviral agents, kinase inhibitors).
Agrochemical Synthesis:
Precursor to herbicides/pesticides with lipophilic cyclopentyl motifs.
Material Chemistry:
Monomer for functionalized polymers (e.g., nitrile rubber modifiers).
Hazards: Irritant (skin/eyes), harmful if inhaled/swallowed.
Storage: 2–8°C under inert gas (sensitive to moisture/polymerization).
PPE Required: Gloves, goggles, fume hood.
Supplier Examples:
TCI Chemicals (Cat. C2629)
Combi-Blocks (Cat. ST-0969)
Why It Matters: Combines the reactivity of acrylonitrile with the steric/electronic effects of cyclopentyl – enabling tailored molecular design in drug discovery.
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