3-Cyclopentylacrylonitrile
[CAS# 591769-05-0]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 3-Cyclopentylacrylonitrile
• Synonyms: (2E)-3-Cyclopentylprop-2-enenitrile
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• CAS Registry Number: 591769-05-0
• EC Number: 630-363-6
• SMILES: C1CCC(C1)/C=C/C#N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.57, Calc.^*
• Boiling Point: 209.0±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 79.9±11.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS08;GHS09 Danger
• Risk Statements: H227-H301-H311-H314-H331-H351-H411-H412
• Safety Statements: P203-P210-P260-P261-P262-P264-P270-P271-P273-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P318-P321-P330-P361+P364-P363-P370+P378-P391-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

3-Cyclopentylacrylonitrile is an organic compound that consists of a cyclopentyl group attached to the acrylic acid backbone with a nitrile (CN) group at the terminal position. It belongs to the class of nitrile-containing compounds, which are of significant interest in both synthetic and industrial chemistry.

The discovery and synthesis of 3-cyclopentylacrylonitrile are rooted in the broader exploration of acrylonitrile derivatives, which have been studied for their versatility in organic synthesis. Acrylic acid derivatives, particularly those with nitrile groups, exhibit interesting reactivity patterns, which are valuable in a range of chemical transformations. The specific substitution pattern in 3-cyclopentylacrylonitrile, with the cyclopentyl group at the 3-position, contributes to its unique chemical and physical properties, making it a valuable building block for further synthetic applications.

3-Cyclopentylacrylonitrile is used primarily as an intermediate in organic synthesis. The presence of both a nitrile group and a double bond in the compound makes it highly reactive, particularly in reactions such as Michael additions and other nucleophilic addition processes. This reactivity is important for the synthesis of more complex molecules, such as polymers, pharmaceuticals, and fine chemicals. In particular, the nitrile functionality can undergo various transformations, such as hydrolysis to carboxylic acids, or can be used in the formation of amides or other derivatives.

One significant application of 3-cyclopentylacrylonitrile is in the synthesis of specialty polymers. Due to its conjugated system with the nitrile and double bond, it can be polymerized to form materials with unique properties. For example, copolymerization with other monomers, such as styrene or acrylates, allows the creation of polymers with enhanced thermal stability, chemical resistance, and mechanical properties. These polymers find uses in industries such as coatings, adhesives, and electronics.

In addition to its role in polymer chemistry, 3-cyclopentylacrylonitrile has been used in the synthesis of various biologically active compounds. Its reactivity allows for the incorporation of the cyclopentyl group into larger molecular frameworks, which can enhance the pharmacological properties of the resulting compounds. These derivatives may exhibit activity in fields such as anti-inflammatory, anticancer, or antimicrobial research. By modifying the nitrile group or the double bond, researchers can fine-tune the structure of these compounds to optimize their biological effects.

Furthermore, 3-cyclopentylacrylonitrile is also useful in the preparation of functionalized materials for applications in organic electronics. The unique combination of the nitrile group and conjugated double bond makes it a potential candidate for the development of organic semiconductors, which are used in electronic devices such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs). The properties of the cyclopentyl group may also be advantageous for tuning the solubility and stability of such materials.

In summary, 3-cyclopentylacrylonitrile is an important organic intermediate used in the synthesis of specialty polymers, biologically active compounds, and materials for organic electronics. Its chemical structure, which includes a nitrile group and conjugated double bond, provides it with significant reactivity, making it a valuable building block for a variety of synthetic applications. The well-established uses of 3-cyclopentylacrylonitrile highlight its importance in both academic research and industrial processes, particularly in materials science and pharmaceutical development.

References

2014. Ruxolitinib. Pharmaceutical Substances.