635708-74-6

Basic information

• Product Name: 1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE
• Synonyms: 2-HEPTEN-4-YNE, 1-CHLORO-6,6-DIMETHYL-, (2Z)-;1-Chloro-6,6-dimetnyl-2-heptene-4-yne;(Z)-1-chloro-6,6-diMethylhept-2-en-4-yne;Terbinafine Related Compound 3;(2Z)-1-Chloro-6,6-dimethyl-2-hepten-4-yne;(2E)-1-Chloro-6,6-dimethyl-2-hepten-4-yne
• CAS NO: 635708-74-6
• Molecular Formula: C₉H₁₃Cl
• Molecular Weight: 156.65
• Mol File: 635708-74-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 207.5±23.0 °C(Predicted)
• Appearance: /
• Density: 0.946±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE(635708-74-6)
• EPA Substance Registry System: 1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE(635708-74-6)

Safety Data

• Hazardous Substances Data: 635708-74-6(Hazardous Substances Data)

Usage

Uses

(2Z)-1-Chloro-6,6-dimethyl-2-hepten-4-yne is a byproduct in the synthesis of Terbinafine Hydrochloride (T107500); an orally active, antimycotic allylamine related to Naftifine. It is a specific inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Also antifungal.

Upstream product

• 78629-20-6 3-hydroxy-6,6-dimethylhept-1-ene-4-yne 

Downstream Products

• 78628-80-5 terbinafine hydrochloride 
• 176168-78-8 N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthylmethyl amine hydrochloride 
• 78628-81-6 (Z)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine 

Relevant articles and documents

A PROCESS FOR THE PURIFICATION OF 1-HALO-6,6-DIMETHYL-HEPT-2-ENE-4-YNE

The invention relates to a process for purification of 1-halo-6,6-dimethyl-hept-2-ene-4-yne of Formula (I), wherein X represents a halogen atom subjecting crude 1-halo-6,6-dimethyl-hept-2-ene-4-yne to distillation under reduced pressure to obtain pure 1-halo-6,6-dimethyl-hept-2-ene-4-yne. This compound is an important intermediate for the production of the widely used antifungal drug Terbinafine.

A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: A key intermediate for terbinafine

A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4- yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1(max)). The resulting (E)-1-halo-6,6- dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally related enyne alcohols have been studied likewise and shown similar versatility. (C) 2000 Elsevier Science Ltd.