7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one
[CAS# 5307-99-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one
• Synonyms: NSC 116987
• Molecular Formula: C₇H₆Cl₂O
• Molecular Weight: 177.03
• CAS Registry Number: 5307-99-3
• EC Number: 226-165-0
• SMILES: C1C=CC2C1C(=O)C2(Cl)Cl

Properties

• Solubility: Slightly soluble (4.1 g/L) (25 °C), Calc.^*
• Density: 1.44±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.515
• Boiling point: 60-65 °C (2.5 Torr)^**
• Flash point: 114.1±26.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Nee, Michael

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H315-H319
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P321-P330-P332+P317-P337+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one is an organic compound notable for its bicyclic structure and its significance in synthetic organic chemistry. The discovery of this compound can be traced back to studies focusing on bicyclic ketones, which were of interest due to their unique structural properties and potential applications in various chemical reactions. Its distinct configuration and the presence of chlorine substituents make it a valuable intermediate in the synthesis of more complex organic molecules.

The molecular structure of 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one features a bicyclic framework with two fused rings and a carbonyl group, providing a versatile platform for further chemical modifications. The introduction of chlorine atoms at the 7-position enhances the compound’s reactivity, making it suitable for a variety of synthetic transformations. Researchers have explored this compound in different chemical contexts, contributing to its recognition as an important building block in organic synthesis.

One of the primary applications of 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one lies in its role as an intermediate in the synthesis of biologically active compounds. Its ability to participate in various reactions, including nucleophilic additions and cycloadditions, allows chemists to construct more complex structures that may possess pharmaceutical properties. For example, this compound can be utilized to create derivatives that exhibit antimicrobial, antiviral, or anticancer activity, making it of interest in medicinal chemistry.

Additionally, the compound's unique structure lends itself to applications in the field of materials science. The reactivity of the dichloro-substituted bicyclic system can be exploited to develop new materials with specific properties, such as polymers or functionalized coatings. Researchers have investigated the potential of such materials in applications ranging from drug delivery systems to advanced coatings with enhanced durability and chemical resistance.

Moreover, 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one has found use in the development of synthetic methodologies. Its unique reactivity can facilitate the formation of various functional groups, contributing to the advancement of new synthetic routes in organic chemistry. For instance, its involvement in cycloaddition reactions can lead to the formation of cyclopropane derivatives, which are valuable intermediates in numerous organic transformations.

In summary, 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one is an important compound in synthetic organic chemistry, recognized for its distinctive structure and reactivity. Its applications span medicinal chemistry, materials science, and the development of synthetic methodologies, underscoring its significance as a versatile building block in organic synthesis. Ongoing research continues to explore its potential, enhancing our understanding of its chemical behavior and expanding its applications in various fields.

References

Jeremy Robertson and Thomas G. Fowler. Synthesis and Claisen rearrangement of bridged bicyclic enol ethers of relevance to the course of ketene s-cis-diene cycloaddition, Org. Biomol. Chem., 2006, 4, 4307.