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

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

Usage

Insecticide and acaricide

Target

Central nervous system of pests

Effect on Pests

Paralysis and death

Agricultural Applications

Control of mites, aphids, and insects in crops like apples, pears, cotton, and potatoes

Toxicity

Highly toxic

Systemic Nature

Non-systemic

Human Health Risks

Skin and eye irritation, respiratory issues, potential carcinogenic effects with prolonged exposure

Environmental Impact

Harmful to the environment

Regulatory Status

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

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

Downstream Products

• 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 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 124-40-3 dimethyl amine 

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.

Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis

A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative ortho-substituent, could be obtained in good to excellent yields by using 0.3 mol% palladium acetate as catalyst. Features of the protocol including cost-effectiveness of diarylborinic acids, efficacy to heteroatom ortho-substituted substrates and high chemoselectivity to aryl chlorides have been clearly demonstrated in practical synthesis of fungicide Boscalid.

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.

Antimalarial activity of 1-aryl-3,3-dialkyltriazenes

The antimalarial activity of 1-aryl-3,3-dialkyltriazenes to Plasmodium berghei NK-65 in infected mice was evaluated at an intraperitoneal dose of 100 mg/kgbw. Some of these compounds were found to possess potent antimalarial activity.

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%).

Waste-Free Quantitative Gas/Solid Diazotation Using Nitrogen Dioxide and Triazene Synthesis, Both Avoiding Liquid Phases

Solid diazonium nitrates (2a-j) are quantitatively obtained by reaction of crystalline anilines (1a-j) with gaseous nitrogen dioxide. Solid diazonium salts react quantitatively with dimethylamine to give the triazenes (4a-j). Wastes that are typical for the previous syntheses of these compounds in solution are avoided. Atomic force microscopic (AFM) investigations indicate long-range molecular movements due to phase rebuilding. The features thus formed are related to the known crystal structures of the starting anilines. The diazotations run to completion, because, after accumulation of product molecules, phase transformation to give the product lattices leads to crystal disintegration and thus to formation of fresh surface over and over.

AFM in organic solid state reactions

Organic solid-state reactions are probed with the atomic force microscope (AFM). In all cases phase rebuilding gives rise to characteristic submicroscopic features which change in shape due to phase transformation in later stages of the chemical reaction. Photo-(E/Z)-isomerization of olefin 1 occurs in the crystal, photodimerization of 9-chloroanthracene 3 is used as a probe for characterizing the luminosity distribution of SNOM-tips. Gas/solid imbibition in chiral host 5 proceeds enantiospecifically. Histidine crystals form the dihydrochloride with HCl, ammonia and methylamine react face-selectively with crystalline adipic acid 8, furane-2-carboxylic acid 10 and 2-mercaptobenzothiazole 12. Crystals of olefin 14 add chlorine. Solid-state diazotations and subsequent transformations of the solid diazonium nitrates into triazenes occur quantitatively. Solid/solid pinacol- and benzilic acid rearrangements are probed with the AFM. The features formed by long range molecular movements relate to the crystal packing and are thus different on different faces. Correlations with X-ray structural data are demonstrated. All reactions proceed to completion on a preparative scale and do not produce wastes as do their less selective counterparts if performed in solution. Organic solid-state reactions, AFM, SNOM-tip, imbibition, salt formations, chlorination, diazotations, triazene, gas/solid-reactions, solid/solid-reactions, crystal packing, waste-free reactions.