4,5-Dimethoxy-1-cyanobenzocyclobutane
[CAS# 35202-54-1]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 4,5-Dimethoxy-1-cyanobenzocyclobutane
• Synonyms: 1-Cyano-4,5-dimethoxybenzocyclobutene; 4,5-Dimethoxy-1-benzocyclobutenecarbonitrile; 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• CAS Registry Number: 35202-54-1
• EC Number: 609-091-7
• SMILES: COC1=C(C=C2C(CC2=C1)C#N)OC

Properties

• Density: 1.18±0.1 g/cm³, Calc.^*
• Melting point: 83-84 °C
• Index of Refraction: 1.557, Calc.^*
• Boiling Point: 345.9±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 140.6±21.1 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4,5-Dimethoxy-1-cyanobenzocyclobutane is a chemical compound that has garnered attention in the field of organic chemistry due to its unique molecular structure and potential applications in synthetic chemistry. This compound consists of a benzocyclobutane ring system, which is substituted with methoxy and cyanide functional groups at specific positions. The combination of the aromatic benzene ring, the cyclobutane ring, and the methoxy and cyanide groups contributes to the compound's interesting chemical properties and reactivity.

The discovery of 4,5-Dimethoxy-1-cyanobenzocyclobutane arose from research aimed at exploring the reactivity of substituted benzocyclobutane derivatives. The cyclobutane ring is known for its strained structure, which often leads to high reactivity, making these compounds valuable in organic synthesis. The methoxy and cyanide groups are electron-donating and electron-withdrawing, respectively, which affects the reactivity and stability of the compound. This makes 4,5-Dimethoxy-1-cyanobenzocyclobutane a versatile molecule for various synthetic applications.

The synthesis of 4,5-Dimethoxy-1-cyanobenzocyclobutane typically involves the cyclization of precursor compounds that incorporate the necessary functional groups. The cyanide group, being a good nucleophile, is often introduced under controlled conditions, while the methoxy groups are introduced through etherification reactions. The synthesis of this compound requires careful attention to reaction conditions, as the presence of multiple functional groups can lead to side reactions if not properly managed.

One of the primary applications of 4,5-Dimethoxy-1-cyanobenzocyclobutane lies in the field of medicinal chemistry. The unique structure of the compound makes it an attractive candidate for the development of new drug-like molecules. The methoxy and cyanide substituents can be used as handles for further chemical modifications, allowing for the synthesis of derivatives with potentially improved pharmacological properties. For example, such compounds could be designed to target specific enzymes or receptors involved in various diseases, including cancer and neurodegenerative disorders.

The compound also finds use in the development of novel materials. The unique structure and functional groups of 4,5-Dimethoxy-1-cyanobenzocyclobutane may be useful in the design of new polymers or materials with specific electronic or optical properties. Additionally, the ability to modify the chemical structure of the compound allows researchers to fine-tune its properties for specific applications in material science.

In conclusion, 4,5-Dimethoxy-1-cyanobenzocyclobutane is a valuable compound in both synthetic and medicinal chemistry. Its distinctive molecular structure, combined with the reactivity of its functional groups, makes it a useful building block for the development of new drugs and materials. As research into its properties and applications continues, this compound is likely to play an important role in the discovery of novel therapeutic agents and advanced materials.

References

2014. The new synthesis and characterization of SBA-15-Pr–NMe3OH: a tailored and reusable Bronsted base nanoreactor for the conversion of nitriles into amides using H2O2. Journal of Porous Materials, 22(2).
DOI: 10.1007/s10934-014-9887-3

2006. Ivabradine. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0081