7203-90-9

Basic information

• Product Name: 1-(4-chlorophenyl)-3,3-dimethyltriazene
• Synonyms: 1-(4-chlorophenyl)-3,3-dimethyltriazene
• CAS NO: 7203-90-9
• Molecular Formula: C₈H₁₀ClN₃
• Molecular Weight: 183.66
• Mol File: 7203-90-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 302.33°C (rough estimate)
• Flash Point: 101.2°C
• Appearance: /
• Density: 1.2295 (rough estimate)
• Vapor Pressure: 0.0315mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• CAS DataBase Reference: 1-(4-chlorophenyl)-3,3-dimethyltriazene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)-3,3-dimethyltriazene(7203-90-9)
• EPA Substance Registry System: 1-(4-chlorophenyl)-3,3-dimethyltriazene(7203-90-9)

Safety Data

• Hazardous Substances Data: 7203-90-9(Hazardous Substances Data)

Usage

General Description

1-(4-chlorophenyl)-3,3-dimethyltriazene, also known as chlordimeform, is a chemical compound primarily used as an insecticide and acaricide. It is a highly toxic and non-systemic substance that works by targeting the central nervous system of pests, ultimately leading to paralysis and death. Chlordimeform is commonly used in agriculture to control a variety of pests, including mites, aphids, and insects in crops such as apples, pears, cotton, and potatoes. Despite its efficacy as a pesticide, chlordimeform is also known to be harmful to humans and the environment, with potential health risks such as skin and eye irritation, respiratory issues and potential carcinogenic effects with prolonged exposure. As a result, its use has been restricted or banned in some countries.

InChI:InChI=1/C8H10ClN3/c1-12(2)11-10-8-5-3-7(9)4-6-8/h3-6H,1-2H3/b11-10+

Upstream product

• 124-40-3 dimethyl amine 
• 106-47-8 4-chloro-aniline 
• 2028-74-2 p-chlorobenzenediazonium chloride 

Downstream Products

• 17333-85-6 4-chlorophenyldiazonium salt 
• 124-40-3 dimethyl amine 
• 100-00-5 4-chlorobenzonitrile 
• 106-39-8 bromochlorobenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-46-7 para-dichlorobenzene 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 1309955-77-8 C₁₆H₁₅Cl₂NO₄S₂ 

Relevant articles and documents

Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes

A range of diazonium salts and their corresponding triazenes have been prepared in order to directly compare their relative thermal stabilities (via initial decomposition temperature) from differential scanning calorimetry (DSC) data. A structure-stability relationship has been explored to investigate trends in stability, depending on the aromatic substituent and the structure of the secondary amine component of the diazonium salts and triazenes. All of the triazenes investigated show significantly greater stability (many are stable above 200 °C) compared with the corresponding diazonium salts, which show varying stabilities.

Diazo reactions with unsaturated compounds: XII. Reaction of 1-(p-Carboxybenzenesulfonyl)-1,3-butadiene with aryldiazonium chlorides, 1-aryl-3,3-dimethyl-1-triazenes, and aryldiazonium tetrachlorocuprates(II)

1-(p-Carboxybenzenesulfonyl)-1,3-butadiene reacts in aqueous acetone with aryldiazonium chlorides and 1-aryl-3,3-dimethyl-1-triazenes in the presence of copper(II) chloride and with tetrachlorocuprates(II) to form 1-(p-carboxybenzenesulfonyl)-4-aryl-3-chloro-1-butenes. Nauka/Interperiodica 2007.

1-Aryl-3,3-dialkyltriazenes: A convenient synthesis from dry arenediazonium o-benzenedisulfonimides - A high yield break down to the starting dry salts and efficient conversions to aryl iodides, bromides and chlorides

This research comprises three parts. The first part regards the synthesis of 1-aryl-3,3-dialkyltriazenes 3 by reaction of dry arenediazonium o-benzenedisulfonimides 1, also coming from weakly basic aromatic amines with dimethylamine or diethylamine in aqueous solution at 0-5 °C. Yields were usually greater than 90% and there was the possibility of recovering the o-benzenedisulfonimide (5), which could be reused to prepare the salts 1. In the second part it was demonstrated that there is the possibility of reconverting the triazenes 3 into the starting stable dry salts 1 by using 5 as acid. The reactions were carried out in glacial acetic acid at 50-55 °C and normally afforded salts 1 in yields of around 90-99%. The third part concerns the setting up of two procedures for the conversion of 3 to aryl iodides 9, bromides 10 and chlorides 11. Procedure A used the corresponding aqueous hydrogen halides in acetonitrile at r.t. or 60 °C, sometimes in the presence of aqueous HBF4, sometimes Cu powder (25 examples, yields 65%-88%). Procedure B usually used anhydrous methanesulfonic acid and tetraalkylammonium halides in anhydrous acetonitrile at temperatures varying from r.t. to 80 °C, sometimes in the presence of Cu (16 examples, yields 65-88%).