63170-40-1

Basic information

• Product Name: 4-methyl-1-(1,1,1-trichloromethyl)but-2-enyl acetate
• Synonyms: 4-methyl-1-(1,1,1-trichloromethyl)but-2-enyl acetate;1,1,1-Trichloro-4-methyl-3-penten-2-ol acetate
• CAS NO: 63170-40-1
• Molecular Formula: C₈H₁₁Cl₃O₂
• Molecular Weight: 245.53074
• EINECS: 263-980-0
• Mol File: 63170-40-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 320.1°C at 760 mmHg
• Flash Point: 131.6°C
• Appearance: /
• Density: 1.277g/cm³
• Vapor Pressure: 0.000324mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: 4-methyl-1-(1,1,1-trichloromethyl)but-2-enyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-1-(1,1,1-trichloromethyl)but-2-enyl acetate(63170-40-1)
• EPA Substance Registry System: 4-methyl-1-(1,1,1-trichloromethyl)but-2-enyl acetate(63170-40-1)

Safety Data

• Hazardous Substances Data: 63170-40-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11Cl3O2/c1-3-4-5-7(8(9,10)11)13-6(2)12/h4-5,7H,3H2,1-2H3/b5-4+

Upstream product

• 72800-48-7 1,1,1-trichloro-4-methyl-3-penten-2-ol 
• 108-24-7 acetic anhydride 
• 73986-07-9 1,1,1-Trichloro-2-oxo-4-methyl-3-pentene 
• 67-66-3 chloroform 
• 56269-68-2 3-methylbut-2-enylidene diacetate 

Downstream Products

• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 52315-02-3 3t-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid-(3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester) 
• 55667-40-8 trans-permethrin acid 
• 59042-49-8 cis-permethrinic acid 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 72800-48-7 1,1,1-trichloro-4-methyl-3-penten-2-ol 
• 135638-44-7 (S)-1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene 

Relevant articles and documents

Practical chemo-enzymatic process for the preparation of (1R,cis)-2-(2,2-dihaloethenyl)-3,3-dimethylcyclopropane carboxylic acids

A practical chemo-enzymatic process for the preparation of optically active (1R,cis)-2-(2,2-dichloro (or dibromo)ethenyl)-3,3-dimethylcyclopropane carboxylic acids (permethrinic or deltamethrinic acids) from racemic 1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene is described. The key intermediate, enantiopure (R)-1,1,1-trichloro-2-hydroxy-4-methyl-3-pentene, is prepared by a lipase catalysed kinetic resolution of the racemic acetate. The reaction mixture, containing (R)-alcohol and the unreacted (S)-acetate, is directly acetylated by a haloacetyl halide, and the products are separated by distillation. The (S)-acetate is racemized, and the (R)-haloacetate is transformed to the corresponding glycinate hydrochloride, followed by diazotization to (R)-1,1,1-trichloro-4-methyl-3-penten-2-yl diazoacetate. The stereoselective carbenic dediazotization of the (R)-diazoacetate furnishes the optically active (1R,4R,5S)-6,6-dimethyl-4-trichloromethyl-3-oxobicyclo[3.2.0]hexan-2-one, which is transformed to the desired enantiopure (1R,cis)-permethrinic or deltamethrinic acid in high optical yield (>99% ee) and overall chemical yield of 10-15%.

AN UNUSUAL REACTION OF TRICHLOROMETHANE WITH ACYLALS IN THE INTERPHASE CATALYSIS CONDITIONS.

Aldehyde diacetates ract with trichloromethane in the standard interphase catalysis conditions to form α-trichloromethylcarbinols or their acetates depending on temperature and time of the reaction.

Electrochemical synthesis of insecticide intermediates

1,1,1-Trihalo-4-methylpentenes, carrying 2-substituents selected from those conjugate bases of Bronsted acids which are leaving groups in beta eliminations, are reduced electrochemically to 1,1-dihalo-4-methylpentadienes, intermediates in the synthesis of pyrethroid insecticides.