60066-53-7

Basic information

• Product Name: ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate
• Synonyms: ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate;ethyl 4，6，6，6-tetrochloro-3，3-dimethyl hexanoate;4,6,6,6-Tetrachloro-3,3-dimethylhexanoic acid ethyl ester;Einecs 262-042-8;Hexanoic acid, 3,3-dimethyl-4,6,6,6-tetrachloro-, ethyl ester;Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl ester
• CAS NO: 60066-53-7
• Molecular Formula: C₁₀H₁₆Cl₄O₂
• Molecular Weight: 310.04484
• EINECS: 262-042-8
• Mol File: 60066-53-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 314.9°C at 760 mmHg
• Flash Point: 109.9°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 0.000454mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate(60066-53-7)
• EPA Substance Registry System: ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate(60066-53-7)

Safety Data

• Hazardous Substances Data: 60066-53-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16Cl4O2/c1-4-16-8(15)6-9(2,3)7(11)5-10(12,13)14/h7H,4-6H2,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 7796-72-7 ethyl 3,3-dimethylpent-4-enoate 
• 109-73-9 N-butylamine 

Downstream Products

• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 60066-84-4 ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)-cyclopropanecarboxylate 
• 63142-57-4 ethyl (+/-)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 60066-84-4 ethyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate 

Relevant articles and documents

Studies on sulfinatodehalogenation: The addition reaction of halocarbons with olefins initiated by sodium dithionite

Halocarbons such as carbon tetrachloride, CCl3Br, CF3CCl3, BrCF2CF2Br, BrCF2CFClBr and CF2Br2, reacted with olefins in the presence of the sulfinatodehalogenation reagent sodium dithionite under mild conditions to give the corresponding adducts. In the case of F113, CFCl2CF2CFCl2 and CF3Cl3, the polyfluoroalkylation product resulted.

A Convenient Synthesis of Ethyl 3-(2,2-Dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates and Its Modifications for cis-Isomer Enrichment

A synthesis of the title compounds 5 involves the reaction between 3-methyl-2-buten-1-ol and triethyl orthoacetate to produce ethyl 3,3-dimethyl-4-pentenoate, which is followed by the addition of various carbon tetrahalides to the double bond.The reaction of resulting adducts with a base affords 5 in high yields.Stereoselective preparation of the cis-isomer was achieved by the following two methods: First one involves selective transformation of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate to ethyl 6,6,6-trichloro-2,3-dimethyl-4-hexanoate (8a) with piperidine followed by the selective conversion of 8a to cis-2,2-dichloroethenyl compound (cis-5a).Second one is based on the stereoselective cyclization of ethyl 4,6,6,6-tetrachloro-3,3-dimethyl-hexanoate (t-BuONa/solvent/HMPA) to ethyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate which is transformed into cis-5a without cis-trans isomerisation.

Process for preparing dihalovinylcyclopropanecarboxylates

Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a γ-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.