Cyanuric chloride
[CAS# 108-77-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: Cyanuric chloride
• Synonyms: 2,4,6-Trichloro-1,3,5-triazine; 2,4,6-Trichloro-s-triazine
• Molecular Formula: C₃Cl₃N₃
• Molecular Weight: 184.41
• CAS Registry Number: 108-77-0
• EC Number: 203-614-9
• SMILES: C1(=NC(=NC(=N1)Cl)Cl)Cl

Properties

• Density: 1.92
• Melting point: 145-148 °C
• Boiling point: 190 °C
• Water solubility: reacts
• Flash point: 200 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H330-H302-H314-H317
• Safety Statements: P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P320-P321-P330-P333+P317-P342+P316-P362+P364-P363-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Respiratory sensitization	Resp. Sens.	1	H334
Skin sensitization	Skin Sens.	1A	H317
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 2670

Discovery and Applications

Cyanuric chloride (C3Cl3N3), also known as 2,4,6-trichloro-1,3,5-triazine, is a heterocyclic compound that was first synthesized in the 19th century. The compound consists of an s-triazine ring, which is a six-membered ring containing three carbon atoms and three nitrogen atoms, each of which is bonded to a chlorine atom. The discovery of cyanuric chloride is attributed to early chemical studies on the properties of triazines, which revealed its potential as a versatile intermediate in organic synthesis.

Cyanuric chloride is a white crystalline solid with a melting point of 146-147°C and a boiling point of 190°C. It is moderately soluble in water but highly soluble in organic solvents such as acetone, benzene, and chloroform. The presence of three chlorine atoms on the triazine ring makes cyanuric chloride highly reactive, especially towards nucleophiles, making it a valuable reagent in a variety of chemical reactions.

One of the main uses of cyanuric chloride is in the agrochemical industry, where it is a key intermediate in the synthesis of a number of herbicides and pesticides. It is used in the production of triazine-based herbicides such as atrazine and simazine, which are effective in controlling a wide range of weeds.

Cyanuric chloride is widely used in the dye and pigment industry, where it is used to produce reactive dyes that form covalent bonds with textile fibers to produce bright, long-lasting colors. These dyes are particularly important in the textile industry, where they are used to dye fabrics made from cotton, wool, and other natural fibers.

In the pharmaceutical industry, cyanuric chloride is an important building block used in the synthesis of a variety of pharmaceutical compounds, including antiviral, antibacterial, and anticancer agents. Its reactivity allows the introduction of functional groups that are critical to the biological activity of these drugs.

Cyanuric chloride plays a role in water treatment processes, where it is used to produce cyanuric acid, which is a stabilizer for chlorine in swimming pools. Cyanuric acid helps prevent chlorine from being rapidly degraded by sunlight, thereby maintaining its disinfecting properties for a longer period of time.

The polymer industry also benefits from the reactivity of cyanuric chloride, where it is used as a crosslinker in the production of high-performance polymers. These polymers exhibit improved thermal stability, chemical resistance, and mechanical properties, making them suitable for a variety of industrial applications.

Cyanuric chloride is a versatile organic synthesis reagent used to produce a variety of specialty chemicals, including intermediates for the synthesis of surfactants, lubricants, and plasticizers. Its ability to introduce triazine rings into molecules enhances the properties of the final product.

Cyanuric chloride is a hazardous substance that must be handled with care. It can cause severe irritation to the skin, eyes, and respiratory tract. Inhalation or ingestion of cyanuric chloride can cause serious health problems. When working with this compound, appropriate personal protective equipment (PPE), including gloves, goggles, and adequate ventilation, must be used to minimize the risk of exposure.

Cyanuric chloride can pose an environmental risk if not properly managed. It is important to control its release to the environment through appropriate control, handling, and disposal methods. Regulatory measures are in place to ensure safe handling and minimize its environmental footprint.

References

2024. Highly selective alcohol oxidation by polyvinyl cyanuric chloride in DMSO: a metal- and catalyst-free approach. Research on Chemical Intermediates.
DOI: 10.1007/s11164-024-05444-w

2019. Preparation of a stable and robust nanobiocatalyst by efficiently immobilizing of pectinase onto cyanuric chloride-functionalized chitosan grafted magnetic nanoparticles. Journal of Colloid and Interface Science.
DOI: 10.1016/j.jcis.2018.10.053

2009. Biosensor for luteolin based on silver or gold nanoparticles in ionic liquid and laccase immobilized in chitosan modified with cyanuric chloride. The Analyst.
DOI: 10.1039/b911952c