Cyanuric chloride

Description

Cyanuric chloride is a very cheap reagent due to the fact that it is the main precursor to the very common herbicide atrazine. The cost effectiveness of cyanuric chloride makes it an attractive option for some large scale applications.

Chemical properties

White Powder

The Uses of Cyanuric chloride

Cyanuric Chloride is extensively used in the preparation of the triazine-class pesticides and herbicides. Cyanuric chloride is also used as a precursor to dyes and crosslinking agents due to the react ive chlorine atoms towards nucleophilic substitution reactions. Cyanuric chloride derivatives possess a large spectrum of activities as antibacterial and anticancer agents.

The Uses of Cyanuric chloride

The SM (39.4 g, 149.98 mmol) and DIEA (51.69 mL, 300 mmol) were dissolved in THF (550 mL) and stirred at -10 C under N2. Then a solution of isobutylchloroformate in THF (50 mL) was added dropwise and stirring was continued for 1 h at -10 C, then 1 h at RT. NaBH4 (17.02 g, 450 mmol) was added portionwise at -10 C and stirred for 1 h. H2O (200 mL) was added cautiously to the reaction mixture and stirring was continued for another hour at RT under N2. The mixture was neutralized with 10% citric acid (aq) and then was extracted with EtOAc. The org layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (50:50:0 to 0:100:0 to 0:99:1 heptane/DCM/MeOH) to provide the product as a white powder. [23.9 g, 64%]

The Uses of Cyanuric chloride

Cyanurchloride is an intermediate to manufacture of agrochemicals (triazine herbicides), dyestuffs, optical brighteners, tanning agents, reactive dyes, UV-absorbing agent, softening agents and pharmaceuticals, as well as block-builders for plastics. Product Data Sheet

The Uses of Cyanuric chloride

Cyanurchloride is an intermediate to manufacture of agrochemicals, dyestuffs, optical brighteners, tanning agents, softening agents and pharmaceuticals, as well as block-builders for plastics.

The Uses of Cyanuric chloride

Reagent for the conversion of alcohols to chlorides and for the immobilization of microorganisms and enzymes.1

The Uses of Cyanuric chloride

Intermediate in the synthesis of active dyes, agricultural products, and drug substances. Reagent in organic synthesis. Coupling agent for nucleic acids and proteins; cyanuric chloride-activated paper is used in capillary and electroblotting applications, dot tests, and hybridization protocols.

Definition

ChEBI: A chloro-1,3,5-triazine in which the triazine ring is substituted on each carbon by chlorine. Its main use is in the preparation of the triazine-class pesticides.

Production Methods

Cyanuric chloride is obtained by the trimerization of cyanogen chloride in organic solvents, in the presence of acidic catalysts, and carried out in a gaseous phase at 200–500C. Cyanuric chloride is used as a chemical intermediate. It is the precursor to the herbicide atrazine.

General Description

A colorless crystalline solid with a pungent odor. Melting point 146°C. Density 1.32 g / cm3. Very slightly soluble in water. Toxic by ingestion and inhalation of vapors. Irritates skin and eyes. Used to make dyes.

Air & Water Reactions

Reacts exothermically with water, especially if catalyzed or heated, to generate fumes of hydrochloric acid. Very slightly soluble in water.

Reactivity Profile

Cyanuric chloride reacts rapidly and exothermically with water to generate hydrogen chloride. A mixture with water in an industrial reactor with refrigeration turned off developed pressure that blew gaskets and filled the building with flammable vapors. An explosion occurred when the vapors were ignited [MCA Case History 1869(1972)]. Runaway reactions have occurred with acetone/water; methanol/water, ethoxyethanol/water, allyl alcohol/sodium hydroxide/water, 2-butanone/sodium hydroxide/water, and methanol/sodium bicarbonate [Loss Prev. Bull., 1979, (25), 21]. Reacts with methanol to give gaseous methyl chloride. Reacts rapidly with bicarbonates to generate gaseous carbon dioxide. Reacts vigorously with dimethyl formamide (DMF) to form carbon dioxide after a deceptive induction period [BCISC Quart. Safety Summ., 1960, 35, 24]. Can react with reducing agents to generate heat and products that may be gaseous (causing pressurization of closed containers). The products may themselves be capable of further reactions (such as combustion in the air).

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Vapors may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Flammability and Explosibility

Non flammable

Safety Profile

Poison by ingestion, inhalation, and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Experimental reproductive effects. A corrosive. A skin and severe eye irritant. An allergen. Has been reported as causing irritation of mucous membranes and heart rhythm disturbances in humans. Violent reaction with water - (above 30°C), acetone + water, methanol, methanol + sodium hydrogen carbonate, 2- ethoxyethanol, dimethyl formamide, 3- butanone + sodium hydroxide + water, allyl alcohol + sodium hydroxide + water (at 28℃). When heated to decomposition it emits toxic fumes of Cland NOx. See also CHLORIDES.

Purification Methods

TCT crystallises from CCl4 or pet ether (b 90-100o) and is dried under vacuum. It has also been recrystallised twice from anhydrous *benzene immediately before use [Abuchowski et al. J Biol Chem 252 3582 1977]. [Beilstein 26 III/IV 66.]