Tributyltin Chloride: CAS 1461-22-9, Properties & Toxicity
Explore tributyltin chloride (CAS 1461-22-9), including its chemical structure, molecular formula, boiling point, InChI, toxicity and environmental effects.
Tributyltin Chloride: Structure, Properties, Toxicity and Scientific Applications
A scientific guide to tributyltin chloride (CAS 1461-22-9), covering its chemical identity, molecular structure, physical properties, biological effects, environmental impact and laboratory research significance.
1. What Is Tributyltin Chloride?
Tributyltin chloride, also known as tri-n-butyltin chloride or tributylchlorotin, belongs to the organotin family of compounds. These substances contain at least one carbon–tin chemical bond.
The chemical has attracted considerable scientific attention because of its toxic effects on organisms and its historical association with marine antifouling formulations.
Tributyltin compounds have also been investigated in toxicology, endocrine disruption, environmental chemistry and cell biology.
It is important to distinguish tributyltin chloride from other tributyltin derivatives, including tributyltin oxide and tributyltin acetate. Although related, these compounds have different chemical identities and may have different reported physical properties.
2. Chemical Structure, Formula and InChI
Tributyltin chloride has the general structural formula (C4H9)3SnCl. Its central tin atom is bonded to three n-butyl groups and one chlorine atom.
This arrangement gives the molecule a combination of organometallic and organic characteristics that influence its physicochemical behavior.
| Identifier | Value |
|---|---|
| Common name | Tributyltin chloride |
| IUPAC name | Tributyl(chloro)stannane |
| CAS number | 1461-22-9 |
| Molecular formula | C12H27ClSn |
| Linear formula | (CH3CH2CH2CH2)3SnCl |
| SMILES | CCCC[Sn](CCCC)(CCCC)Cl |
| InChIKey | GCTFWCDSFPMHHS-UHFFFAOYSA-M |
| EC Number | 215-958-7 |
| PubChem CID | 15096 |
What Is the InChI of Tributyltin Chloride?
The standard InChI is an internationally recognized representation of a chemical structure. It supports compound identification across scientific databases.
InChI=1S/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1
Researchers can use the CAS number, InChI, InChIKey and canonical SMILES to retrieve structural information from chemical databases.
3. Physical and Chemical Properties of Tributyltin Chloride
Physical and chemical properties influence the behavior, laboratory characterization and environmental fate of tributyltin chloride.
Published values may differ slightly depending on purity, temperature, pressure and the reference source.
| Property | Reported Value |
|---|---|
| Molecular formula | C12H27ClSn |
| Molecular weight | Approximately 325.5 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Boiling point | 171–173°C at 25 mmHg |
| Melting point | Approximately -9°C; reported value |
| Density | Approximately 1.20 g/mL |
| Water solubility | Limited; varies with conditions |
| Organic solvent solubility | Soluble in many common organic solvents |
What Is the Boiling Point of Tributyltin Chloride?
Does Tributyltin Chloride Dissolve in Water?
Tributyltin chloride has limited water solubility and exhibits strong affinity for organic phases and environmental particles. Its behavior in aquatic environments is influenced by pH, dissolved organic matter, and chemical speciation.
The compound's physical properties help explain why organotin contamination is relevant to sediments and marine ecosystems.
4. Historical Uses of Tributyltin Compounds
Tributyltin compounds were historically used because of their biological activity against microorganisms and marine fouling organisms.
Marine Antifouling Coatings
Tributyltin-based substances were historically incorporated into marine antifouling paints to reduce the accumulation of organisms on submerged ship surfaces.
However, their release into aquatic environments was associated with serious ecological effects, particularly in marine invertebrates.
Biocidal Applications
Certain organotin compounds were historically investigated or used in biocidal and material-protection applications.
These historical uses do not imply that tributyltin chloride is suitable or legally permitted for current commercial applications.
Scientific Research
Tributyltin chloride continues to be investigated in controlled scientific settings as a substance of interest in toxicology, environmental chemistry, and molecular research.
5. Biological Effects and Molecular Mechanisms
Tributyltin chloride has been studied for its effects on cellular signaling, metabolic regulation, immune function and endocrine systems.
Endocrine Disruption
Tributyltin is recognized in experimental research as an endocrine-disrupting organotin compound. It can interfere with signaling pathways involved in cellular differentiation and metabolic homeostasis.
PPAR-Gamma and RXR Signaling
Research has shown that tributyltin can influence peroxisome proliferator-activated receptor gamma (PPARγ) and retinoid X receptor (RXR) signaling.
These nuclear receptors participate in adipocyte differentiation, lipid metabolism and broader transcriptional regulation.
Adipogenesis and Metabolic Research
Tributyltin has been investigated as an experimental obesogenic substance because of its capacity to influence adipogenic pathways in cellular and animal models.
Findings from experimental studies should not automatically be interpreted as direct evidence of equivalent health outcomes in humans.
Immune and Cellular Effects
Organotin exposure has also been associated with changes in immune responses, mitochondrial function, oxidative stress and cellular viability in experimental research.
6. Tributyltin Chloride Toxicity and LD50 in Mice
Tributyltin chloride is a hazardous chemical that requires careful occupational and environmental risk management.
Toxicological studies have investigated acute toxicity, repeated-exposure effects, endocrine disruption and adverse effects on biological systems.
What Is the LD50 of Tributyltin Chloride in Mice?
LD50 refers to the median lethal dose estimated to cause death in 50% of a specified test population under defined experimental conditions.
LD50 is not a safe exposure level, an occupational exposure limit, or a clinical dosing recommendation.
| Study Endpoint | Reported Value | Context |
|---|---|---|
| Mouse oral LD50 | 60 mg/kg | Historical experimental reference |
| Rat oral LD50 | 129 mg/kg | Historical experimental reference |
Potential Toxicological Effects
Depending on the exposure route and duration, tributyltin chloride may present hazards involving acute toxicity, irritation, organ toxicity and reproductive effects.
Its exact hazard classification should be obtained from the current safety data sheet for the supplied material and applicable regulatory classifications.
7. Environmental Impact and Ecotoxicity
Tributyltin compounds are widely studied because of their toxicity to aquatic organisms and their environmental persistence.
Marine Ecosystem Effects
Historically, tributyltin-based antifouling systems introduced organotin substances into marine environments.
These compounds have been associated with adverse effects in molluscs, including reproductive abnormalities and altered development.
Imposex in Gastropods
Imposex is a condition in which female gastropod molluscs develop male sexual characteristics. It is a well-documented biological effect associated with environmental exposure to tributyltin.
Environmental Persistence
Tributyltin species can associate with suspended particles and sediments, influencing their distribution and environmental residence time.
Environmental degradation depends on conditions such as oxygen availability, light exposure, microbial activity, temperature and sediment properties.
Bioaccumulation
Tributyltin can accumulate in aquatic organisms and enter food webs. Its behavior depends on chemical speciation and environmental conditions.
Why Is Tributyltin Environmentally Important?
Tributyltin compounds demonstrate how chemicals developed for effective industrial applications can produce substantial unintended ecological effects. Their environmental history remains important in pollution control, ecotoxicology and chemical regulation.
8. Laboratory and Research Applications
Tributyltin chloride is relevant primarily as a subject of scientific investigation, rather than as a general-purpose laboratory reagent.
Toxicological Research
Investigation of chemical toxicity, biological responses and mechanisms of cellular injury.
Endocrine Disruption
Study of nuclear receptor signaling, metabolic regulation and endocrine-related biological effects.
Environmental Monitoring
Investigation of organotin residues and contamination in environmental samples and ecosystems.
Cellular Mechanisms
Research involving cellular signaling, viability, differentiation and molecular responses to chemical exposure.
Analytical Chemistry
Method development and validation for detecting organotin compounds in appropriate analytical matrices.
Aquatic Toxicology
Investigation of toxic effects associated with organotin exposure in aquatic organisms.
The relevance of tributyltin chloride to these research areas does not remove the need for institutional approvals, controlled laboratory procedures and appropriate hazardous chemical management.
9. Safety, Handling and Regulatory Considerations
Tributyltin chloride should be treated as a hazardous substance because of its toxicological and environmental properties.
Laboratory Safety
- Consult the current supplier-specific safety data sheet before any handling.
- Follow institutional hazardous chemical procedures and exposure controls.
- Use suitable protective equipment selected through a laboratory risk assessment.
- Prevent uncontrolled environmental release.
- Segregate and dispose of contaminated materials as hazardous waste.
International Antifouling Restrictions
The International Convention on the Control of Harmful Anti-fouling Systems on Ships entered into force on 17 September 2008.
It establishes restrictions on harmful organotin compounds used as biocides in ship antifouling systems.
Restrictions on the manufacture, supply, use, transport and disposal of tributyltin chloride may vary across jurisdictions.
10. Frequently Asked Questions About Tributyltin Chloride
What is tributyltin chloride?
Tributyltin chloride is an organotin compound with the molecular formula C12H27ClSn. It is studied in toxicology, environmental chemistry and related scientific disciplines.
What is the CAS number of tributyltin chloride?
The CAS Registry Number of tributyltin chloride is 1461-22-9.
What is the molecular formula of tributyltin chloride?
Its molecular formula is C12H27ClSn and its molecular weight is approximately 325.5 g/mol.
What is the boiling point of tributyltin chloride?
A commonly reported boiling point is 171–173°C at 25 mmHg. This value is measured under reduced pressure.
What is the InChIKey of tributyltin chloride?
The standard InChIKey is GCTFWCDSFPMHHS-UHFFFAOYSA-M.
What is tributyltin chloride LD50 in mice?
Historical toxicological sources report an oral LD50 of approximately 60 mg/kg in mice. This is an experimental toxicity measure, not a safe exposure level.
Is tributyltin chloride toxic?
Yes. Tributyltin chloride is hazardous and is associated with significant toxicological and environmental risks. Its handling requires appropriate safety controls.
What is tributyltin chloride used for?
Tributyltin chloride is investigated in research involving chemical toxicity, environmental contamination, endocrine disruption and organotin chemistry.
Why are tributyltin compounds restricted?
Their historical use in marine antifouling coatings caused serious ecological concerns, particularly toxicity to aquatic organisms and reproductive effects in molluscs.
Conclusion
Tributyltin chloride (CAS 1461-22-9) is an organotin compound of continuing interest in chemical science, toxicology and environmental research.
Its chemical structure, physicochemical properties and biological activity help explain its importance in scientific investigations.
Understanding its toxicological characteristics and environmental impact is essential for interpreting published research and applying appropriate laboratory safety and regulatory practices.
Scientific Sources and Further Reading
- National Institute of Standards and Technology. Stannane, tributylchloro-. Chemistry WebBook. NIST chemical record .
- National Center for Biotechnology Information. PubChem Compound Summary for Tributyltin Chloride, CID 15096. PubChem record .
- International Maritime Organization. International Convention on the Control of Harmful Anti-fouling Systems on Ships. IMO reference .
- The environmental obesogen tributyltin chloride acts via peroxisome proliferator activated receptor gamma to induce adipogenesis in murine 3T3-L1 preadipocytes. Peer-reviewed article .