Butyltin trichloride
[CAS# 1118-46-3]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organotin
• Name: Butyltin trichloride
• Synonyms: Butyltrichlorotin; Butyltrichlorostannane
• Molecular Formula: C₄H₉Cl₃Sn
• Molecular Weight: 282.16
• CAS Registry Number: 1118-46-3
• EC Number: 214-263-6
• SMILES: CCCC[Sn](Cl)(Cl)Cl

Properties

• Density: 1.693
• Boiling point: 93 ºC (10 mmHg)
• Refractive index: 1.5215-1.5245
• Flash point: 81 ºC
• Water solubility: SOLUBLE

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H314-H315-H318-H319-H332-H335-H341-H360-H372-H400-H410
• Precautionary Statements: P203-P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	1B	H360
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1	H314
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H312
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 3265

Discovory and Applicatios

Butyltin trichloride, also known as tributyltin chloride (TBTCl), is an organotin compound with the molecular formula C12H27Cl3Sn. It is a colorless to pale yellow liquid characterized by its strong, unpleasant odor. Butyltin trichloride was first synthesized in the early 20th century, but it gained commercial significance in the 1950s and 1960s as researchers began to explore its unique properties and potential applications.

The production of butyltin trichloride typically involves the reaction of tin(IV) chloride with butyl lithium or butyl magnesium halides. The resulting compound has significant industrial applications due to its excellent biocidal and antifouling properties. Butyltin trichloride is primarily used as a precursor for various organotin compounds, particularly in the manufacturing of antifouling paints for ships and marine structures. These paints help prevent the growth of marine organisms on vessel hulls, significantly improving fuel efficiency and reducing maintenance costs.

In addition to its application in marine coatings, butyltin trichloride is also utilized in the production of stabilizers for polyvinyl chloride (PVC) and other polymers. The compound acts as a heat stabilizer, preventing degradation during processing and extending the lifespan of the final product. This application is crucial in the plastics industry, where durability and resistance to environmental factors are essential.

Butyltin trichloride is employed in the synthesis of various other organotin compounds, which have diverse uses in agriculture, such as biocides and fungicides. These derivatives exhibit potent antifungal and antibacterial properties, making them valuable in protecting crops from pathogens and pests. However, the use of organotin compounds, including butyltin trichloride, has raised environmental and health concerns due to their toxicity and persistence in the environment.

Due to its potential hazards, the use of butyltin trichloride and its derivatives has come under scrutiny. The compound has been shown to be highly toxic to marine life, leading to the banning of TBT-based antifouling paints in many countries. As a result, researchers and manufacturers are now exploring alternative, less toxic materials for use in marine coatings and agricultural applications.

Despite the environmental concerns associated with butyltin trichloride, it remains an important compound in industrial chemistry. Ongoing research aims to develop safer alternatives while continuing to explore the potential applications of organotin chemistry in various fields. Regulatory agencies worldwide have established guidelines to ensure the safe handling and use of butyltin trichloride in industrial settings, balancing its benefits with necessary precautions to protect human health and the environment.

In conclusion, butyltin trichloride is a significant organotin compound with diverse applications in marine coatings, plastics, and agriculture. Discovered in the early 20th century and commercialized in the mid-20th century, it has played a crucial role in various industries. However, due to its toxicity and environmental impact, its use is increasingly regulated, leading to a search for safer alternatives in the industry.

References

2017. The importance of environmental factors and matrices in the adsorption, desorption, and toxicity of butyltins: a review. Environmental Science and Pollution Research International.
DOI: 10.1007/s11356-017-8449-z

2020. Synthesis of novel organotin(IV) complex for multiple applications: as biologically potent and single molecular precursor. Journal of the Iranian Chemical Society.
DOI: 10.1007/s13738-020-02027-5

2022. Accumulation and degradation of organotin compounds in cultivated sporophytes of the brown alga Undaria pinnatifida. Journal of Applied Phycology.
DOI: 10.1007/s10811-021-02670-2