1-Chloro-6,6-dimethyl-5-hept-2-en-4-yne
[CAS# 126764-17-8]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Chloro-6,6-dimethyl-5-hept-2-en-4-yne
• Synonyms: 1-Chloro-6,6-dimethyl-2-hepten-4-yne
• Molecular Formula: C₉H₁₃Cl
• Molecular Weight: 156.65
• CAS Registry Number: 126764-17-8
• EC Number: 603-158-4
• SMILES: CC(C)(C)C#C/C=C/CCl

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.475, Calc.^*
• Boiling Point: 207.5±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 74.7±18.0 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P302+P352-P305+P351+P338-P321-P405-P501

Discovery and Applications

1-Chloro-6,6-dimethyl-5-hept-2-en-4-yne is an organochlorine compound with a distinct molecular structure that includes both an alkyne and an alkene functional group. This dual functionality provides the compound with unique chemical reactivity, making it valuable in organic synthesis and specialized chemical applications.

The discovery and synthesis of structurally similar halogenated alkynes date back to early developments in alkyne chemistry. Researchers have explored such compounds for their potential in coupling reactions, selective halogenation, and transformations that lead to more complex molecular architectures. The presence of the chlorine atom in 1-chloro-6,6-dimethyl-5-hept-2-en-4-yne allows for further derivatization, making it a useful intermediate in organic synthesis.

One of the primary applications of this compound is in the field of synthetic chemistry, where it serves as a building block for the development of pharmaceuticals, agrochemicals, and materials with specialized properties. Its alkyne and alkene functionalities enable participation in a range of catalytic transformations, including Sonogashira and Heck coupling reactions. These reactions facilitate the construction of complex molecules with potential biological and industrial significance.

In addition to its role in synthesis, halogenated alkynes similar to 1-chloro-6,6-dimethyl-5-hept-2-en-4-yne have been investigated for their reactivity in polymerization and materials science. The combination of a reactive triple bond and a halogen substituent allows for controlled modifications in macromolecular structures, leading to polymers with tailored properties such as enhanced thermal stability and improved mechanical strength.

As chemical industries continue to seek new synthetic methodologies and functional materials, compounds like 1-chloro-6,6-dimethyl-5-hept-2-en-4-yne remain of interest for their versatility in organic transformations. Ongoing research focuses on optimizing reaction conditions and expanding the range of applications for these halogenated alkynes, further highlighting their relevance in modern chemistry.

References

2006. Identification of impurities in the production of terbinafine hydrochloride. Pharmaceutical Chemistry Journal, 40(8).
DOI: 10.1007/s11094-006-0150-3

2004. A Simple Method for Obtaining Terbinafine Hydrochloride. Pharmaceutical Chemistry Journal, 38(4).
DOI: 10.1023/b:phac.0000038420.81588.50