5333-82-4

Basic information

• Product Name: α-(Trichloromethyl)-4-chlorobenzenemethanol
• Synonyms: 1-(4-Chlorophenyl)-2,2,2-trichloroethanol;p-Chloro-α-(trichloromethyl)benzenemethanol;α-(Trichloromethyl)-4-chlorobenzenemethanol;BenzeneMethanol, 4-chloro-.alpha.-(trichloroMethyl)-
• CAS NO: 5333-82-4
• Molecular Formula: C₈H₆Cl₄O
• Molecular Weight: 259.94464
• Mol File: 5333-82-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 47-48 °C
• Boiling Point: 326.7°C at 760 mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 1.559g/cm³
• Vapor Pressure: 8.59E-05mmHg at 25°C
• Refractive Index: 1.596
• PKA: 11.72±0.20(Predicted)
• CAS DataBase Reference: α-(Trichloromethyl)-4-chlorobenzenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: α-(Trichloromethyl)-4-chlorobenzenemethanol(5333-82-4)
• EPA Substance Registry System: α-(Trichloromethyl)-4-chlorobenzenemethanol(5333-82-4)

Safety Data

• Hazardous Substances Data: 5333-82-4(Hazardous Substances Data)

Usage

General Description

α-(Trichloromethyl)-4-chlorobenzenemethanol is a chemical compound that is the active ingredient in the pesticide Chloropicrin. It is a potent soil fumigant and is primarily used to control and eliminate soil-borne pathogens, pests, and weeds in agricultural settings. This chemical is a highly toxic and corrosive substance that can cause severe irritation and damage to the skin, eyes, and respiratory system upon exposure. It is also considered a potential environmental hazard due to its persistence in soil and water. Proper handling, storage, and disposal of α-(Trichloromethyl)-4-chlorobenzenemethanol are essential to prevent harm to human health and the environment.

InChI:InChI=1/C8H6Cl4O/c9-6-3-1-5(2-4-6)7(13)8(10,11)12/h1-4,7,13H

Upstream product

• 67-66-3 chloroform 
• 104-88-1 4-chlorobenzaldehyde 
• 650-51-1 sodium trichloroacetate 
• 75-87-6 chloral 
• 75-62-7 Bromotrichloromethane 
• 56-23-5 tetrachloromethane 
• 13086-93-6 (acetyloxy)(4-chlorophenyl)methyl acetate 
• 108-90-7 chlorobenzene 
• 27704-37-6 2,2,2-trichloro-1-(4-chlorophenyl)ethanone 
• 555-31-7 aluminum isopropoxide 

Downstream Products

• 63253-06-5 2-benzoyloxy-1,1,1-trichloro-2-(4-chloro-phenyl)-ethane 
• 63252-99-3 2,2,2-trichloro-(4-chlorophenyl)ethyl acetate 
• 63253-13-4 1,1,1-trichloro-2-(4-chloro-phenyl)-2-hexanoyloxy-ethane 
• 63253-07-6 1,1,1-trichloro-2-(4-chloro-phenyl)-2-propionyloxy-ethane 
• 63253-09-8 1,1,1-trichloro-2-(4-chloro-phenyl)-2-isobutyryloxy-ethane 
• 63253-08-7 2-butyryloxy-1,1,1-trichloro-2-(4-chloro-phenyl)-ethane 
• 63253-00-9 1,1,1-trichloro-2-chloroacetoxy-2-(4-chloro-phenyl)-ethane 
• 66681-61-6 2-bromoacetoxy-1,1,1-trichloro-2-(2,4-dichloro-phenyl)-ethane 
• 50-29-3 p,p'-DDT 
• 17925-97-2 1,1,1-trichloro-2-(4-chloro-phenyl)-2-p-tolyl-ethane 
• 63253-15-6 1,1,1-trichloro-2-(4-chloro-phenyl)-2-octanoyloxy-ethane 
• 128348-58-3 2,2,2-trichloro-1-(4-chlorophenyl)ethyl methyl ether 
• 4329-01-5 1,1,1-trichloro-2-(4-chloro-phenyl)-2-phenyl-ethane 
• 63253-17-8 1,1,1-trichloro-2-(4-chloro-phenyl)-2-palmitoyloxy-ethane 

Relevant articles and documents

A novel β-(oxy)alkyl radical during copper(I)-mediated stereoselective synthesis of (Z)-ene-1,4-diones in a reaction of 2,2,2-trichloro-1-phenylethanone

A novel β-(oxy)alkyl radical derived from trichloro methyl compound containing neither a suitably located C-C multiple bond nor a leaving group or a H-atom at the β-position of the radical in a reaction of 2,2,2-trichloro-1-phenyl-ethanone with 2 mol equiv each of CuCl and bpy in refluxing DCE under a N2 atm underwent intramolecular heterolysis (just like formation of intact radical cation-anion pair) during stereoselective radical dimerization to Z-ene-1,4-dione along with small amount of reductive dechlorination product. The stereochemistry was established by X-ray diffraction spectroscopy of various solid crystalline products.

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Copper(I)-promoted synthesis of chloromethyl ketones from trichloromethyl carbinols

(Chemical Equation Presented) Reaction of several trichloromethyl carbinols with 2 equiv of CuCl/bpy in refluxing DCE for 3 h afforded chloromethyl ketones in excellent yield by 1,2-H shift in the copper-chlorocarbenoid intermediate.