Chemical Properties
o-Chlorotoluene is a flammable, colorless liquid with an aromatic odor. Insoluble in water, easily soluble in benzene, ethanol, ether and chloroform.
Uses
3-Chlorotoluene was used as catalyst in the synthesis of glycidyl methacrylate grafted multi-walled carbon nanotubes/polypropylene nanocomposites. It was used to study paramagnetic contributions from dioxygen to solute proton spin-lattice relaxation rate constants for a series of aromatic hydrocarbons and drug molecule fragments.
Application
3-Chlorotoluene is used as a reagent to synthesize 4-Arylchromene derivatives, compounds that induce apoptosis and act as anti-cancer agents. 3-Chlorotoluene is also used as an ingredient in deodorant, and is suspected to cause allergic contact dermatitis in humans.
Preparation
3-Chlorotoluene is obtained from m-toluidine by diazotization and substitution. Add m-toluidine to water, slowly add concentrated hydrochloric acid, and add sodium nitrite solution dropwise at 0-5°C. Then the diazo solution is added to the cuprous chloride for replacement reaction. The crude product generated is distilled to obtain the finished product. If the diazo salt is made into a zinc chloride complex salt of m-toluidine diazo salt, it is decomposed by reflux in ether, and the reactants are cooled, washed and dried. After recovering the ether, it is distilled at atmospheric pressure and m-chlorotoluene is obtained by collecting 160-162°C fraction. The advantage of this method is that the diazonium salt is not easy to hydrolyze and generate phenols.
General Description
3-Chlorotoluene is a colorless liquid. Specific gravity 1.072. Denser than water, thus sinks in water. Flash point less than 141°F. Vapors irritating and narcotic in high concentrations. Used as solvents and as an intermediate for making other chemicals and dyes.
Air & Water Reactions
Flammable. Slightly soluble in water.
Reactivity Profile
3-Chlorotoluene is generally unreactive. May be incompatible with strong oxidizing and reducing agents. May be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
Hazard
Narcotic in high concentration. Avoid
inhalation.
Health Hazard
Inhalation causes upper respiratory irritation. Irritating to skin and eyes. May be absorbed through the skin. Prolonged exposure may result in systemic toxic effects. Harmful if swallowed.
Potential Exposure
o-Chlorotoluene is widely used as a solvent and intermediate in the synthesis of dyes, synthetic rubber; pharmaceuticals; and other organic chemicals. Used as an insecticide, bactericide.
Shipping
UN2238 Chlorotoluenes, Hazard Class: 3; Labels: 3-Flammable liquid.
Purification Methods
Purify it as for 2-chlorotoluene above. [Beilstein 5 IV 806.]
Incompatibilities
Incompatible with acids, alkalis, oxidizers, reducing materials; water
Waste Disposal
In accordance with 40CFR165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
