2,2-Dibutyl-[1,3,2]dioxastannolane: Properties & Lab Use Guide

2,2-Dibutyl-[1,3,2]dioxastannolane is a five-membered cyclic organotin compound widely used as a Lewis acid catalyst and versatile reagent in synthetic organic chemistry, particularly for transesterification, esterification, and selective functionalization of diols and carbohydrate derivatives.

Chemical Name

2,2-Dibutyl-[1,3,2]dioxastannolane

SKU / Product Code

D468142

Compound Class

Cyclic organotin(IV) ester (five-membered 1,3,2-dioxastannolane ring)

Primary Application

Lewis acid catalyst for transesterification, esterification, and regioselective functionalization of polyols

Tin Oxidation State

Sn(IV)

Ring System

Five-membered cyclic dioxastannolane formed from dibutyltin oxide and ethylene glycol

Handling Requirement

Moisture-sensitive; handle under inert atmosphere or in dry conditions

Chemical Identity and Structure

2,2-Dibutyl-[1,3,2]dioxastannolane (SKU: D468142) is a cyclic organotin(IV) compound featuring a five-membered ring in which a tin atom bearing two n-butyl substituents is coordinated by two oxygen atoms derived from ethylene glycol. This dioxastannolane ring system is formally the condensation product of dibutyltin oxide (Bu₂SnO) with ethylene glycol (HOCH₂CH₂OH), with concomitant loss of water. The resulting compound is often described as a cyclic dibutyltin ethylene glycolate. The Sn(IV) center adopts a tetrahedral geometry in the monomeric form, although organotin cyclic esters of this type are known to associate into oligomeric or polymeric structures in the solid state via Sn–O bridging interactions. The Lewis acidic tin center and the strained ring geometry together confer upon this molecule its characteristic reactivity as both a catalyst and an activated acyl-transfer or stannylation reagent.

Synthetic Applications and Reactivity

2,2-Dibutyl-[1,3,2]dioxastannolane is a versatile reagent in synthetic organic chemistry. Its principal applications include:

• Transesterification and esterification: The compound acts as a mild Lewis acid catalyst or a stoichiometric tin alkoxide-type reagent to promote transesterification reactions, often under mild thermal conditions and without requiring strong acids or bases. This is particularly valuable for acid- or base-sensitive substrates.
• Regioselective functionalization of diols and polyols: By forming cyclic stannylene acetals with vicinal or 1,3-diols, dibutyltin-based reagents enable highly regioselective monoprotection, monoalkylation, monoacylation, or monosulfonylation of diol substrates. This strategy is extensively used in carbohydrate chemistry for the selective manipulation of hydroxyl groups in sugars and nucleosides.
• Activation of carbonyl compounds: The Lewis acidic tin center can coordinate to carbonyl oxygen, activating esters, anhydrides, and lactones toward nucleophilic acyl substitution.
• Ring-opening polymerization: Organotin cyclic esters of this class have been explored as initiators or catalysts for the ring-opening polymerization of cyclic esters such as lactides and caprolactone to afford polyesters.

Reactions are typically conducted in aprotic organic solvents such as toluene, THF, DMF, or dichloromethane, often with mild heating to promote turnover.

Safe Handling, Storage, and Waste Disposal

General hazard profile: As an organotin compound, 2,2-Dibutyl-[1,3,2]dioxastannolane should be treated as a potentially toxic substance. Organotin compounds are known to exhibit varying degrees of mammalian toxicity depending on the nature and number of organic substituents; dialkyltin species are generally less acutely toxic than trialkyltin species but should nonetheless be handled with appropriate precautions. Specific toxicological data for this compound should be verified against the current Safety Data Sheet (SDS) prior to use.

Personal protective equipment (PPE): Wear chemically resistant gloves (e.g., nitrile or neoprene), laboratory coat, and safety goggles. Work in a well-ventilated fume hood to avoid inhalation of dusts or vapors.

Moisture sensitivity: The compound is moisture-sensitive. Store under an inert atmosphere (nitrogen or argon) in a tightly sealed container. Keep away from water, protic solvents, and strong oxidizing or reducing agents.

Storage conditions: Store at room temperature or as specified on the product label in a cool, dry location away from incompatible materials. Confirm specific storage temperature requirements with the current product specification sheet.

Waste disposal: Organotin-containing waste must be disposed of as hazardous chemical waste in accordance with local, national, and institutional regulations. Do not pour down the drain. Consult your institution's environmental health and safety (EHS) office for approved disposal procedures.

Procurement, Specifications, and Quality

2,2-Dibutyl-[1,3,2]dioxastannolane is available from Aladdin Scientific under SKU D468142. This product is cross-referenced with Sigma-Aldrich catalog number 725374. Researchers are advised to consult the current Aladdin Scientific product page for up-to-date information on:

• Available pack sizes and pricing
• Current purity grade and analytical specification (e.g., purity by GC or NMR)
• Lot-specific Certificate of Analysis (CoA)
• Safety Data Sheet (SDS) in the required language

When ordering, specify the SKU D468142 to ensure correct product identification. For bulk quantities or custom purity requirements, contact Aladdin Scientific technical sales. Proper documentation including CoA and SDS should be reviewed before use in regulated research environments (e.g., GMP or ISO-accredited laboratories).

Frequently asked questions

What is 2,2-Dibutyl-[1,3,2]dioxastannolane used for in organic synthesis?

It is primarily used as a Lewis acid catalyst and reagent for transesterification, esterification, and the regioselective mono-functionalization of diols and polyols—especially in carbohydrate and nucleoside chemistry. It can also serve as an initiator or catalyst for ring-opening polymerization of cyclic esters.

How should 2,2-Dibutyl-[1,3,2]dioxastannolane be stored to maintain stability?

The compound is moisture-sensitive and should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon), in a cool and dry location. Consult the current product specification sheet and SDS for exact storage temperature requirements.

Is 2,2-Dibutyl-[1,3,2]dioxastannolane hazardous, and what precautions are needed?

As an organotin compound, it should be considered potentially toxic and handled with appropriate PPE including nitrile gloves, lab coat, and safety goggles, and used exclusively in a ventilated fume hood. Organotin waste must be disposed of as hazardous chemical waste per institutional and regulatory guidelines. Always review the current SDS before handling.

What solvents are compatible with 2,2-Dibutyl-[1,3,2]dioxastannolane in typical reactions?

This compound is typically used in aprotic organic solvents such as toluene, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or dichloromethane. Protic solvents such as water or alcohols should generally be avoided due to the compound's moisture sensitivity and potential hydrolysis.

Where can I find the Certificate of Analysis and Safety Data Sheet for SKU D468142?

The Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for SKU D468142 are available on the Aladdin Scientific product page. Search by SKU or product name on the Aladdin Scientific website, or contact customer service directly for lot-specific documentation.

References

1. Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, 2004.
2. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987.
3. Boons, G.-J.; Hale, K. J. Organic Synthesis with Carbohydrates; Sheffield Academic Press: Sheffield, 2000. (Chapter on tin-mediated regioselective functionalization of diols.)
4. Sigma-Aldrich/Merck product page for 2,2-Dibutyl-1,3,2-dioxastannolane, catalog no. 725374. https://www.sigmaaldrich.com/

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.