6111-14-4

Basic information

• Product Name: 4-Methyl-1,1,1-trichloropent-3-en-2-ol
• Synonyms: 4-Methyl-1,1,1-trichloropent-3-en-2-ol;1,1,1-Trichloro-4-methyl-3-penten-2-ol
• CAS NO: 6111-14-4
• Molecular Formula: C₆H₉Cl₃O
• Molecular Weight: 203.4941
• Mol File: 6111-14-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 238.3°Cat760mmHg
• Flash Point: 97.9°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 0.00757mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: 4-Methyl-1,1,1-trichloropent-3-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-1,1,1-trichloropent-3-en-2-ol(6111-14-4)
• EPA Substance Registry System: 4-Methyl-1,1,1-trichloropent-3-en-2-ol(6111-14-4)

Safety Data

• Hazardous Substances Data: 6111-14-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H9Cl3O/c1-4(2)3-5(10)6(7,8)9/h3,5,10H,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 25308-82-1 1,1,1-trichloro-4-methyl-4-penten-2-ol 
• 75-87-6 chloral 
• 115-11-7 isobutene 
• 650-51-1 sodium trichloroacetate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 76-03-9 trichloroacetic acid 
• 63170-40-1 1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene 
• 73986-07-9 1,1,1-Trichloro-2-oxo-4-methyl-3-pentene 
• 67-66-3 chloroform 
• 5936-98-1 trichloromethyltrimethylsilane 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 

Downstream Products

• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 62434-98-4 1,1-dichloro-4-methyl-1,4-pentadiene 
• 135583-14-1 4-Nitro-benzoic acid 3-methyl-1-trichloromethyl-but-2-enyl ester 
• 364633-86-3 malonic acid [(R)-(+)-1-phenylethylamide]-4-methyl-1,1,1-trichloro-3-penten-2-yl ester 
• 1191-99-7 2,3-dihydro-2H-furan 
• 67545-73-7 2,4,4-trimethyl-3-carbomethoxy-5-(β,β-dichlorovinyl)-4,5-dihydrofuran 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 63170-40-1 1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 85101-14-0 Benzoic acid 3-methyl-1-trichloromethyl-but-2-enyl ester 
• 59042-49-8 cis-permethrinic acid 
• 55667-40-8 trans-permethrin acid 
• 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) 
• 65731-84-2 (+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate 

Relevant articles and documents

One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction

(Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope. The method is step-economical, and it nicely complements established one-carbon homologation strategies. (Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope.

One-pot synthesis of trichloromethyl carbinols from primary alcohols

Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.

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%.