What are “organotin” compounds?
Organotin compounds are chemicals that contain at least one carbon–tin (C–Sn) bond in the molecule. By combining the tunability of organic substituents with the reactivity of the tin center, organotins are widely used in organic synthesis, materials chemistry, polymer science, and analytical testing.
A key point for understanding organotin chemistry is:
the organic group (alkyl/aryl/heteroaryl) determines what fragment is carried, while the tin center and its ligands (Cl, H, OAc, OR, etc.) determine how the compound reacts.
How are organotin compounds classified?
Organotins are commonly categorized along two main axes: degree of substitution and functional group/ligand type.
1. Classified by the number of organic groups attached to tin (number of R groups)
- Mono-organotin: RSnX₃ Often behaves like an “organotin salt/precursor,” commonly used to prepare di-/tri-organotin derivatives or as coordination/material precursors.
- Di-organotin: R₂SnX₂, R₂SnO, R₂Sn(OOCR)₂ Very common in materials and catalysis (e.g., di-organotin carboxylates and oxides).
- Tri-organotin: R₃SnX, R₃SnH, R₃SnOOCR Frequently used as synthetic reagents and in organometallic reactions (couplings, radical chemistry, etc.), but many members require greater attention due to toxicity and environmental risk.
- Tetra-organotin: R₄Sn Relatively stable and often encountered as research reagents or intermediates.
2. Classified by ligands/functional groups on tin (which largely determine use)
- Halides: R₃SnCl / Br / I, R₂SnCl₂, etc. → common synthetic precursors
- Hydrides: R₃SnH → classic reagents for radical chemistry (reductions, dehalogenation, etc.)
- Oxides/hydroxides: R₂SnO, R₃SnOH → pronounced Lewis acidity; intermediates and catalysis-related species
- Alkoxides: R₃SnOR, R₂Sn(OR)₂ → convenient for further transformations or condensation/coordination chemistry
- Carboxylates: R₂Sn(OOCR)₂, R₃SnOAc → widely used in materials curing catalysis and additive systems
- Sulfur ligands (e.g., thiolates): R₂Sn(SR)₂ → commonly used in additive applications such as PVC stabilization (with additional compliance and safety considerations)
- Distannanes (R₃Sn–SnR₃): e.g., hexamethylditin → often used to prepare stannyl building blocks or as intermediates in methodology development
Core Applications of Organotin Compounds in Laboratory Chemistry and Research
1. As “carriers of organic fragments”: cross-coupling and building-block chemistry
Many researchers first encounter organotin compounds because they can transfer aryl, alkenyl, heteroaryl, and alkynyl fragments into target molecules—most notably in Stille coupling.
Common classes of organotin building blocks include:
- Alkenyl stannanes (e.g., vinyl/substituted alkenyl trialkylstannanes): for introducing alkenyl motifs
- Allyl stannanes: for constructing allyl-containing frameworks
- Aryl stannanes: general-purpose introduction of aryl fragments
- Heteroaryl stannanes (thiophene, fused thiophenes, pyridine, thiazole, etc.): widely used in materials science, medicinal chemistry, and ligand/backbone design
- Alkynyl stannanes: for introducing alkynyl/aryne-related structural fragments
Why are organotin building blocks still used?
- Broad building-block availability and well-established reaction platforms
- Good compatibility with certain functional-group patterns
- Particularly suitable for constructing conjugated backbones and complex, modular syntheses
A key practical issue that requires special attention:
- Tin residues: organotin species or tin salts may remain in the product and affect downstream performance—especially in materials, bioassays, and device-related applications.
- Common mitigation strategies include adsorption/silica treatment, recrystallization, optimization of chromatographic conditions, and, when necessary, dedicated scavengers (selected case-by-case).
2. As “radical hydrogen sources/chain-transfer reagents”: classic radical chemistry
R₃SnH (e.g., tributyltin hydride) is a classic family of reagents in radical chemistry and can be used for:
- Reduction/dehalogenation of certain organohalides
- Radical cyclizations and mechanistic studies
- Method development (frequently seen in teaching and in classic literature examples)
However, these reagents typically require stricter safety control, and many modern synthetic routes consider alternative systems. In teaching and research, it is worth emphasizing: “can be used” does not mean “should be used casually.”
3. Materials and polymers: from “building blocks” to “catalysts”
In materials science, organotin compounds mainly appear in two roles:
(1) Building blocks for conjugated-material monomers and polymerization
Stannylated aryl/heteroaryl monomers (for example, “bis-stannylated” monomers featuring thienothiophene or benzo[1,2-b:4,5-b']dithiophene scaffolds) are commonly used for:
- Stille polymerization to construct conjugated polymers
- Building and tuning the backbones of organic semiconductors and optoelectronic functional materials
Such monomers are often difunctional (two tin groups per molecule), which facilitates polymer chain growth.
(2) Di-organotin carboxylates/oxides as catalytic or additive components
For example, di-organotin carboxylates can promote, in certain systems:
- Curing of silicone rubbers/sealants
- Polyurethane-related reactions (catalysis, crosslinking/curing, etc.)
- Certain condensation, transesterification, and polymerization processes
Different ligands (e.g., laurate, acetate, 2-ethylhexanoate, etc.) can significantly affect solubility, catalytic activity, and formulation compatibility.
Materials systems are often sensitive to catalyst identity, loading, impurities, and moisture. It is recommended to validate changes within the formulation and process window, rather than substituting purely based on chemical intuition.
4. Analytical testing and environmental relevance: why “organotin” is not one-size-fits-all
Within the organotin family, different forms (methyltin, butyltin, aryltin; mono-/di-/tri-substituted; different ligands) show:
- Different physicochemical properties (volatility, hydrophobicity, stability)
- Markedly different biological and environmental behavior
- Therefore, in applications such as environmental monitoring, pesticide residue testing, and materials migration studies, analytical standards are often required for method development and quality control.
Frequently Asked Question: How do I choose the “right type” of organotin?
Practical selection guidance:
1. To attach a fragment to a molecule (construct a C–C bond)
Also consider: whether downstream workup and purification can effectively remove tin residues.
2. For radical reduction/dehalogenation or other classic radical transformations
→ You may use: R₃SnH (pay close attention to safety controls and waste handling).
3. For materials curing/condensation/polymerization (catalyst or additive applications)
→ Common choices: R₂SnO, R₂Sn(OOCR)₂, and related intermediates (e.g., halides, alkoxides, etc.)
Key considerations: system compatibility, regulatory compliance, and process validation.
4. For standards and quality control (QC)
→ Select: analytical standard grades directly (clear purity specification and intended use).
Laboratory Safety and Handling Notes (Very Important)
In laboratory management, organotin compounds should be treated as toxic/hazardous chemicals, and many also pose environmental risks.
Compliance note: Certain tri-substituted organotin compounds (especially TBT/TPT types) were historically used in antifouling coatings and have been subject to strict international restrictions/bans due to environmental concerns (e.g., requirements under the IMO AFS Convention). In addition, regulations such as EU REACH specify limits and applicable scopes for certain organotin substances (including tri-substituted, dibutyltin, and dioctyltin species) in some consumer products/articles. For materials/additive uses, verify target-market requirements and the customer’s application scenario in advance.
1. Exposure risks and basic principles
- Common exposure routes: inhalation, skin contact, accidental ingestion/contamination
- Some tri-organotin species present higher risks; strengthen protective measures and waste management accordingly.
- Principle: any step that can be performed in a fume hood should never be done openly on the bench.
2. Operational key points
- Fume hood: weighing, transfer, charging, and quenching should be performed in the hood whenever possible
- Personal protection: nitrile gloves (double-gloving when necessary), safety goggles, lab coat; avoid skin exposure. Glove material selection, permeation time, and specific hazard classification should follow the product SDS (organotin species vary widely).
- Avoid cross-contamination: use dedicated pipettes/syringes; wipe bench surfaces promptly; collect contaminated consumables separately
- Storage: keep tightly sealed, cool, and protected from light; segregate from oxidizers/acids/bases as specified in the SDS
- Moisture/air sensitivity: many organotin compounds (especially halides/alkoxides/some building blocks) can be moisture sensitive; dry solvents, inert atmosphere, and/or rapid handling are often more reliable
- Waste: tin-containing liquid/solid waste should generally be collected as organometallic/heavy-metal hazardous waste, clearly labeled “tin-containing”; do not mix with general organic waste (follow institutional requirements)
Aladdin Organotin Product Table (Selection Reference)
To help translate the classification framework into practical selection, an organotin product reference table has been compiled. Following the logic above, products are grouped into:
- Organotin building blocks / coupling monomers (aryl, heteroaryl, alkenyl, alkynyl, and “difunctional bis-stannylated monomers” commonly used in materials)
- Common synthetic precursors / derivatizable intermediates (tri-organotin halides such as R₃SnCl/I/F [and some Br], mono-/di-organotin halides, tri-organotin alkoxides, tri-/di-organotin carboxylates, hydroxides, etc.)
- Radical reagents (typically R₃SnH, including common formats such as standard-concentration solutions and stabilized grades)
- Di-organotin systems for materials and polymer processing (e.g., R₂SnO, R₂Sn(OOCR)₂, commonly used in curing catalysis, condensation/transesterification, etc.)
- Stabilizers / formulation-type products (e.g., sulfur-ligand organotins, maleate esters and other products specified by Sn content)
- Basic organotin intermediates / reference substances (e.g., tetra-organotins R₄Sn, distannanes R₃Sn–SnR₃, etc.)
- Analytical standards (for method development and QC verification)
Product Category | CAS No. | Aladdin Cat. No. | Name | Specification/Purity | Application Highlights / Key Features |
Conjugated materials/polymer monomer building block (bis(trimethylstannyl)) | 2376193-84-7 | (4,8-Bis(4-chloro-5-(2-butyloctyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) | – | Conjugated-material monomer; difunctional building block for Stille coupling/polymerization | |
Conjugated materials/polymer monomer building block (bis(trimethylstannyl)) | 2131164-64-0 | (4,8-Bis(5-(2-butyloctyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) | – | Conjugated-material monomer; difunctional building block for Stille coupling/polymerization (fluorinated) | |
Conjugated materials/polymer monomer building block (bis(trimethylstannyl)) | 1402460-13-2 | (4,8-Bis(5-(2-butyloctyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) | – | Conjugated-material monomer; difunctional building block for Stille coupling/polymerization | |
Conjugated materials/polymer monomer building block (bis(trimethylstannyl)) | 1449302-74-2 | 1,1'-[(2,3,5,6-Tetrafluoro-1,4-phenylene)bis(5,2-thiophenediyl)]B bis[1,1,1-trimethylstann- | – | Difunctional building block for Stille coupling/polymerization; tetrafluorophenyl motif enhances electron-accepting character | |
Conjugated materials/polymer monomer building block (bis(trimethylstannyl)) | 2100300-07-8 | 1,1'-[(1E)-1,2-Ethenediylbis(4-fluoro-5,2-thiophenediyl)]bis[1,1,1-trimethylstann- | – | Difunctional building block for Stille coupling/polymerization; vinyl-bridged (extended conjugation) | |
Heteroaryl SnBu3 building block (thiophene-type) | 54663-78-4 | 2-(Tributylstannyl)thiophene | ≥97% | Stille coupling building block; thiophene fragment introduction (materials/medchem general use) | |
Heteroaryl SnBu3 building block (common in Stille) | 160032-41-7 | (Thieno[3,2-b]thiophen-2-yl)tributylstannane | – | Stille coupling building block; commonly used in conjugated backbones/materials | |
Heteroaryl SnBu3 building block (common in Stille) | 2453212-69-4 | (Selenopheno[3,2-b]thiophen-2-yl)tributylstannane | – | Stille coupling building block; Se-containing heterocycle for conjugated backbone construction | |
Alkenyl SnBu3 building block (common in Stille) | 7486-35-3 | Tributyl(vinyl)tin | ≥98% | Introduces vinyl group via Stille coupling; widely used in materials and methodology | |
Alkenyl SnBu3 building block (common in Stille) | 7486-35-3 | Tributyl(vinyl)tin | ≥97% | Introduces vinyl group via Stille coupling; widely used in materials and methodology | |
Allyl/alkenyl SnBu3 building block | 24850-33-7 | Allyltributyltin | ≥97% | Allyl/alkenyl transfer; commonly used in coupling and methodology studies | |
Allyl/alkenyl SnBu3 building block | 67883-62-9 | (Methylallyl)tributyltin | ≥95% | Allyl/substituted-allyl introduction; organic synthesis building block | |
Alkynyl SnBu3 building block (ethynyl-type) | 3757-88-8 | T752249 | Tributyl(phenylethynyl)tin | ≥60% | Alkynyl fragment introduction; coupling/methodology building block (lower-grade specification) |
Alkynyl SnBu3 building block (ethynyl-type) | 3757-88-8 | Tributyl(phenylethynyl)tin | ≥95% | Alkynyl fragment introduction; coupling/methodology building block (high purity) | |
Aryl SnBu3 building block (phenyl) | 960-16-7 | Tributyl(phenyl)tin | ≥95% | Aryl building block for Stille coupling; phenyl fragment introduction | |
Fluorinated alkenyl trimethylstannane building block | 51583-40-5 | Fluoroalkenyltrimethylstannane | - | Fluorinated alkenyl introduction; building block for coupling/methodology/materials | |
Allyl tri-organotin (Ph3Sn–allyl) | 76-63-1 | Allyltriphenyltin | ≥95% | Allyl transfer/coupling-related; organometallic methodology intermediate | |
Mono-organotin halide (RSnCl3) | 1118-46-3 | Butyltin trichloride | Analytical standard | Organotin precursor/intermediate; also used as analytical standard/QC | |
Mono-organotin halide (RSnCl3) | 1118-46-3 | Butyltin trichloride | ≥95% | Organotin precursor/intermediate (for preparing di-/tri-organotin derivatives) | |
Tri-organotin halide (R3SnCl) | 1461-22-9 | Tributyltin chloride | ≥96% | Common organotin precursor; for preparing R3SnX/R3SnH/carboxylates, etc. | |
Tri-organotin halide (R3SnCl) | 1461-22-9 | Tributyltin chloride | Analytical standard | Common organotin precursor; analytical standard/QC | |
Tri-organotin halide (R3SnI) | 7342-47-4 | Tributyltin iodide | – | Organotin halide; intermediate for synthesis/transformations | |
Tri-organotin halide (R3SnF) | 1983-10-4 | Tributyltin fluoride | ≥95% (W) | Organotin reagent form; intermediate for synthesis/transformations | |
Tri-organotin halide (Me3SnCl) | 1066-45-1 | Trimethyltin chloride | Analytical standard | Tin source/synthetic precursor; analytical standard/QC | |
Tri-organotin halide (Me3SnCl) | 1066-45-1 | Trimethyltin chloride | ≥97% | Tin source/synthetic precursor; often used to prepare Me3Sn derivatives | |
Tri-organotin halide solution (Me3SnCl) | 1066-45-1 | Trimethyltin chloride solution | 1.0 M in THF | Convenient dosing; for synthesis/transformations | |
Tri-organotin halide solution (Me3SnCl) | 1066-45-1 | Trimethyltin chloride solution | 1.0 M in hexanes | Convenient dosing; for synthesis/transformations | |
Tri-organotin halide (Me3SnBr) | 1066-44-0 | Trimethyltin bromide | ≥98% | Tin source/synthetic precursor; for other Me3Sn derivatives | |
Tri-organotin halide (Et3SnBr) | 2767-54-6 | Triethyltin bromide | ≥95% | Organotin reagent; synthetic intermediate (control toxicity/exposure) | |
Tri-organotin halide (Ph3SnCl) | 639-58-7 | Triphenyltin chloride | Analytical standard | Aryl organotin precursor; analytical standard/QC | |
Tri-organotin halide (Ph3SnCl) | 639-58-7 | Triphenyltin chloride | ≥96% | Aryl organotin precursor; intermediate for synthesis/materials research | |
Tri-organotin alkoxide (R3SnOR) | 1067-52-3 | Tributyltin methoxide | ≥97% | Organotin alkoxide intermediate; alcoholysis/transformations/coordination chemistry | |
Tri-organotin carboxylate (R3SnOAc) | 56-36-0 | T283450 | Tributyltin acetate | ≥98% | Organotin acetate intermediate; synthesis/coordination/materials applications |
Tri-organotin hydroxide (Me3SnOH) | 56-24-6 | Trimethyltin hydroxide | ≥98% | Synthetic intermediate; for preparing other Me3Sn derivatives/salts | |
Tri-organotin oxide / bis(tributyltin) oxide | 56-35-9 | Tributyltin oxide | Analytical standard | Organotin oxide; analytical standard/QC (also used as synthesis/materials intermediate) | |
Tri-organotin oxide / bis(tributyltin) oxide | 56-35-9 | Tributyltin oxide | ≥96% | Organotin oxide; synthesis/materials intermediate (historically also linked to antifouling use) | |
Tri-organotin hydride (R3SnH, radical reagent) | 688-73-3 | Tributyltin hydride solution | 1 M in cyclohexane | Radical reduction/dehalogenation; solution form for convenient dosing/scale-up | |
Tri-organotin hydride (R3SnH, radical reagent) | 688-73-3 | T684458 | Tributyltin hydride (with BHT stabilizer) | ≥96%, containing BHT stabilizer | Radical reduction/dehalogenation; BHT helps reduce auto-oxidation |
Tri-organotin hydride (R3SnH, radical reagent) | 688-73-3 | Tri-n-butyltin hydride | ≥97%, contains 0.05% BHT stabilizer | Radical reduction/dehalogenation; stabilized (high purity) | |
Tri-organotin hydride (R3SnH, radical reagent) | 688-73-3 | T731793 | Tri-n-butyltin hydride | ≥90%, contains 0.05% BHT stabilizer | Radical reduction/dehalogenation; stabilized (economy grade) |
Di-organotin halide (R2SnCl2) | 683-18-1 | D114139 | Dibutyltin dichloride | Analytical standard | Di-organotin precursor; analytical standard/QC |
Di-organotin halide (R2SnCl2) | 683-18-1 | D137748 | Dibutyltin dichloride | ≥97% (T) | Di-organotin precursor; synthesis/materials intermediate |
Di-organotin halide (same substance, different naming) | 683-18-1 | D433318 | Dibutyltin dichloride | Suitable for synthesis | Di-organotin precursor; synthesis/materials intermediate (same as “dibutyltin dichloride”) |
Di-organotin halide (sterically hindered) | 19429-30-2 | Di-tert-butyltin dichloride | ≥98% | Bulky; intermediate for organic synthesis/coordination chemistry | |
Di-organotin halide (Me2SnCl2) | 753-73-1 | Dimethyltin dichloride | ≥98% | Methyltin precursor; materials/stabilizer intermediate | |
Di-organotin halide (Me2SnCl2) | 753-73-1 | Dimethyltin dichloride | Analytical standard | Methyltin precursor; analytical standard/QC | |
Di-organotin halide (octyl) | 3542-36-7 | D189118 | Dioctyltin dichloride | ≥97% | Intermediate for materials/stabilizers; highly hydrophobic |
Di-organotin alkoxide (R2Sn(OR)2) | 1067-55-6 | Dibutyltin dimethoxide | ≥95% | Sol–gel/organic synthesis intermediate; for further coordination/condensation | |
Di-organotin oxide (R2SnO) | 818-08-6 | Dibutyltin oxide | Suitable for synthesis | Lewis acid catalysis/condensation; materials and synthesis intermediate | |
Di-organotin oxide (R2SnO) | 818-08-6 | Dibutyltin oxide | ≥98% | Lewis acid catalysis/condensation; high-purity grade | |
Di-organotin oxide (R2SnO) | 818-08-6 | Dibutyltin oxide | Analytical standard | Analytical standard/QC; also used as synthesis reference | |
Di-organotin carboxylate (R2Sn(OAc)2) | 1067-33-0 | Dibutyltin diacetate | ≥95% (W) | Catalyst/intermediate; transesterification/silanol condensation/materials systems | |
Di-organotin carboxylate (DBTDL, catalyst) | 77-58-7 | Dibutyltin dilaurate (DBTDL) | ≥95% | PU/silicone curing catalyst; widely used high-efficiency tin catalyst | |
Di-organotin carboxylate (dioctyltin dilaurate) | 3648-18-8 | Dioctyltin dilaurate | ≥98% | PVC stabilization/material additive (depends on regulations and use scenario); also seen in materials systems | |
Di-organotin carboxylate (2-ethylhexanoate) | 2781-10-4 | Dibutyltin diisooctanoate | – | Common in PU/silicone catalyst formulations | |
Di-organotin halide (R₂SnCl₂) | 867-36-7 | Di-n-propyltin dichloride | Analytical standard | Organotin intermediate; analytical standard/QC | |
Organotin thiolate/stabilizer (R2Sn(SR)2) | 1185-81-5 | Dibutyltin bis(dodecylthiolate) | ≥95% | Thiolate stabilizer for PVC heat stability/anti-aging (additives) | |
Organotin thiolate stabilizer (methyltin mercaptide) | 57583-35-4 | Methyltin mercaptide | Sn: 19% | PVC heat stability/processing stabilizer additive | |
Di-organotin carboxylate (maleate/fumarate type) | 78-04-6 | Dibutyltin maleate | ≥95% | PVC stabilization/material additive; carboxylate-type organotin | |
Organotin stabilizer (octyltin maleate ester; specified by Sn content) | 16091-18-2 | Octyltin maleate ester | Sn: 25%–27% | PVC stabilization/material additive; formulation-type product defined by Sn content | |
Dioctyltin (octyl, standard) | 3542-36-7 | Dioctyltin, analytical standard | Analytical standard | Analytical standard/QC | |
Distannane (dual-tin reagent) | 661-69-8 | Hexamethylditin | ≥98% (GC) | Methyl stannylation/precursor for Me3Sn building blocks; coupling and methodology intermediate | |
Distannane (dual-tin reagent) | 661-69-8 | Hexamethylditin | ≥97% | Same as above; building-block precursor | |
Tetra-organotin (R4Sn) | 594-27-4 | Tetramethyltin | ≥98% | Common tetra-organotin; research reagent/reference | |
Tetra-organotin (R4Sn) | 594-27-4 | Tetramethyltin | Suitable for synthesis | Tetra-organotin intermediate for synthesis | |
Tetra-organotin (R4Sn) | 1461-25-2 | Tetrabutyltin | ≥95% | Tetra-organotin intermediate/research reagent; hydrophobic and stable | |
Tetra-organotin (R4Sn) | 1461-25-2 | Tetrabutyltin | Analytical standard | Analytical standard/QC; also used as research reference | |
Tetra-organotin (R4Sn) | 1461-25-2 | T432129 | Tetra-n-butyltin | Suitable for synthesis | Tetra-organotin intermediate for synthesis |
Tetra-organotin (R4Sn) | 2176-98-9 | Tetrapropyltin | ≥95% | Tetra-organotin intermediate/research reagent | |
Tetra-organotin (R4Sn) | 1449-55-4 | Tetracyclohexyltin | ≥99% | Bulky, highly hydrophobic; organometallic research/intermediate | |
Tetra-organotin (R4Sn) | 595-90-4 | Tetraphenyltin | ≥97% | Aryl tetra-organotin; research reagent/intermediate | |
Tetra-organotin (R4Sn) | 595-90-4 | Tetraphenyltin | Analytical standard | Analytical standard/QC; also used as reference | |
Tetra-organotin (R4Sn) | 3590-84-9 | Tetraoctyltin | Suitable for synthesis | Highly hydrophobic; materials/intermediate | |
Mixed-substituted tetra-organotin (R4Sn) | 1080-43-9 | Dimethyldiphenyltin | ≥95% | Organometallic research/synthesis intermediate; mixed aryl/methyl substitution | |
Tetra-organotin (alkenyl tin) | 1112-56-7 | Tetra(vinyl)tin | ≥97% | Alkenyl tin monomer; polymerization/coupling/materials intermediate | |
Tetra-organotin (R4Sn) | 2949-42-0 | Tetraisopropyltin | ≥98% | Tetra-organotin intermediate/research reagent | |
Tetra-organotin (allyl tin) | 7393-43-3 | Tetra(allyl)tin | ≥97% | Allyl tin intermediate; potential allyl functionalization/materials research | |
Pesticide/biocide (organotin) analytical standard | 900-95-8 | Fentin (organotin) | Analytical standard | Analytical standard for pesticide/environment/residue testing (organotin class) |
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