Tolyltriazole
[CAS# 29385-43-1]

Identification

• Classification: Catalysts and additives >> UV absorber
• Name: Tolyltriazole
• Synonyms: Methyl-1H-benzotriazole; 5-Methyl-1,2,3-benzotriazole; 5-Methylbenzotriazole; Tolutriazole
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• CAS Registry Number: 29385-43-1
• EC Number: 249-596-6
• SMILES: CC1=CC=CC2=NNN=C12

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.24 g/mL
• Melting point: 141-146 °C
• Index of Refraction: 1.680, Calc.^*
• Boiling Point: 360.6±11.0 °C (760 mmHg), Calc.^*, 160 °C
• Flash Point: 181.5±12.2 °C, Calc.^*
• Water solubility: <0.01 g/100 mL at 18 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319-H332-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P304+P340-P305+P351+P338-P317-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	2	H361d
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Tolyltriazole is a chemical compound belonging to the class of triazoles, which are five-membered heterocyclic compounds containing three nitrogen atoms. Specifically, tolyltriazole consists of a triazole ring substituted with a tolyl group, which is derived from toluene. The discovery of tolyltriazole can be traced back to the early 20th century, a period marked by significant advancements in organic chemistry and the exploration of nitrogen-containing compounds for various applications.

The synthesis of tolyltriazole typically involves the reaction of tolyl hydrazine with an appropriate carbonyl compound, followed by cyclization to form the triazole ring. This compound was initially studied for its potential as a corrosion inhibitor due to its ability to complex with metal ions, particularly copper and its alloys. Researchers soon recognized the compound's effectiveness in protecting metals from corrosion, leading to its adoption in various industrial applications.

One of the primary applications of tolyltriazole is in the field of corrosion protection. It is widely used in the formulation of protective coatings, paints, and varnishes, particularly for metal substrates. When applied to surfaces, tolyltriazole forms a thin film that acts as a barrier against moisture and aggressive environmental agents, thereby preventing rust and corrosion. This application is especially important in industries such as automotive, aerospace, and marine, where the integrity of metal components is critical for safety and performance.

In addition to its role as a corrosion inhibitor, tolyltriazole is employed as a biocide and antifouling agent. Its antimicrobial properties make it effective in controlling the growth of algae, bacteria, and fungi on surfaces, particularly in marine environments. This is particularly useful for marine coatings and antifouling paints, where the accumulation of marine organisms can hinder the performance of vessels and structures. By incorporating tolyltriazole into these formulations, manufacturers can enhance the longevity and effectiveness of marine coatings, reducing maintenance costs and improving overall performance.

Tolyltriazole also finds applications in the formulation of industrial fluids, including lubricants and hydraulic fluids. Its ability to provide corrosion resistance and thermal stability makes it an attractive additive for these products. In hydraulic systems, the presence of tolyltriazole helps to protect metal components from corrosion, extending the life of equipment and reducing the risk of failures.

Moreover, tolyltriazole has been explored for its potential use in agricultural applications. Research has indicated that it may serve as a growth regulator and antifungal agent in certain crops, promoting healthy growth while protecting against pathogenic organisms. This dual functionality makes tolyltriazole a valuable component in developing sustainable agricultural practices.

While tolyltriazole has demonstrated numerous beneficial properties, it is essential to consider the environmental and safety aspects associated with its use. Regulatory agencies are continually evaluating the impact of chemical substances on ecosystems, and guidelines have been established to ensure the safe handling and disposal of tolyltriazole. As with any chemical compound, proper safety measures must be implemented to minimize potential risks to human health and the environment.

In conclusion, tolyltriazole is a versatile chemical compound with significant applications in corrosion protection, biocidal formulations, industrial fluids, and agriculture. Its ability to inhibit corrosion and control microbial growth makes it an invaluable component across various industries. As research continues to evolve, tolyltriazole remains a key player in enhancing the performance and sustainability of materials and products exposed to harsh environmental conditions.

References

2023. Benzotriazole UV stabilizers (BUVs) as an emerging contaminant of concern: a review, _Environmental science and pollution research international_, 30(57)
DOI: https://doi.org/10.1007/s11356-023-30567-9

2023, Clustering micropollutants and estimating rate constants of sorption and biodegradation using machine learning approaches, _npj Clean Water_, 6(1)
DOI: https://doi.org/10.1038/s41545-023-00282-6

2022, A Review on Green Corrosion Inhibitors for Protection of Archeological Metal Artifacts, _Journal of Bio- and Tribo-Corrosion_, 8(2)
DOI: https://doi.org/10.1007/s40735-022-00636-6