1,3-Diallyltetrakis(trimethylsiloxy)disiloxane: Lab Use Guide

1,3-Diallyltetrakis(trimethylsiloxy)disiloxane is a bifunctional organosilicon monomer featuring two reactive allyl groups and a tetrakis(trimethylsiloxy)disiloxane backbone, making it a versatile building block for siloxane polymer synthesis and crosslinking applications.

Product SKU

D942648

Chemical Class

Organosilicon disiloxane monomer with allyl functional groups

Key Functional Groups

Two allyl (–CH₂–CH=CH₂) groups; four trimethylsiloxy (–OSi(CH₃)₃) groups

Primary Applications

Siloxane polymer crosslinking, hydrosilylation substrates, silicone material synthesis

Recommended Storage

Cool, dry, well-ventilated area; away from heat sources, oxidizers, and open flame

Handling Precaution

Use in a fume hood with appropriate PPE; avoid prolonged skin or vapor contact

Chemical Identity and Structure

1,3-Diallyltetrakis(trimethylsiloxy)disiloxane is an organosilicon compound consisting of a central disiloxane (Si–O–Si) unit in which each silicon atom bears one allyl substituent and two trimethylsiloxy (TMS-oxy) groups. The allyl groups confer olefinic reactivity, enabling participation in radical, anionic, and transition-metal-catalyzed reactions such as hydrosilylation. The four flanking trimethylsiloxy groups impart hydrophobicity and contribute to the characteristic low surface energy of siloxane-based materials.

The molecule belongs to the broader class of alkenyl-functional siloxane monomers widely employed as chain extenders or crosslinkers in polydimethylsiloxane (PDMS) networks and specialty silicone elastomers. Its symmetric bifunctional architecture allows predictable incorporation into polymer backbones or networks.

Key Research Applications

Hydrosilylation Crosslinking: The allyl double bonds in 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane react efficiently with Si–H functional polysiloxanes in the presence of platinum or rhodium catalysts (e.g., Karstedt's catalyst). This makes the compound a useful difunctional crosslinker for forming well-defined PDMS or hybrid siloxane elastomeric networks under mild conditions.

Silicone Polymer Synthesis: The compound serves as a bifunctional monomer or chain-end-capping agent in ring-opening polymerization and equilibration reactions of cyclosiloxanes, enabling tailored incorporation of allyl functionality at defined positions along the siloxane chain.

Surface Modification and Coating Research: Allyl-terminated siloxane segments derived from or incorporating this compound are used to introduce siloxane character into organic polymer matrices, improving surface hydrophobicity, flexibility, and thermal stability of composite coatings.

Precursor for Further Functionalization: The allyl groups can be transformed via thiol-ene click chemistry, epoxidation, or hydroformylation, making this compound a platform intermediate for synthesizing more complex siloxane architectures with diverse terminal functionality.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): When handling 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane, wear chemically resistant gloves (e.g., nitrile or neoprene), safety goggles, and a lab coat. Work in a well-ventilated fume hood to minimize inhalation of vapors.

Storage Conditions: Store the reagent in a tightly sealed container in a cool, dry, well-ventilated area away from heat sources, direct sunlight, and incompatible materials such as strong oxidizing agents. Maintain storage temperature as specified on the product label. Prolonged storage may necessitate quality re-verification before use.

Spill and Waste Management: In the event of a spill, contain with inert absorbent material and dispose of in accordance with local regulations governing organosilicon waste. Do not allow the compound to enter drains, waterways, or soil.

Incompatibilities: Strong oxidizers and strong acids may react adversely with this compound. Avoid exposure to ignition sources given the presence of reactive olefinic groups and the flammable nature of organosilicon liquids.

Always consult the current Safety Data Sheet (SDS) for product D942648 before beginning experimental work.

Quality, Purity, and Verification

Research-grade 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane (SKU D942648) from Aladdin Scientific is supplied with a certificate of analysis (CoA) specifying purity and key physical parameters. Researchers should verify the CoA upon receipt and confirm the product meets the requirements of their specific application before use.

Analytical Verification Methods: Purity is typically assessed by gas chromatography (GC) or GC-mass spectrometry (GC-MS). Structural confirmation may be performed by ¹H NMR (characteristic allyl resonances at δ ~5.8–6.0 and ~5.0–5.2 ppm; Si–CH₂ at ~1.6 ppm) and ²⁹Si NMR. Infrared spectroscopy (IR) can confirm Si–O–Si stretching bands (~1000–1100 cm⁻¹) and vinyl C=C stretching (~1630 cm⁻¹).

Lot-to-Lot Consistency: For sensitive polymerization or crosslinking experiments, it is advisable to record the lot number and store unused portions under inert atmosphere (e.g., argon or nitrogen) to prevent premature oxidation or moisture-mediated side reactions.

Ordering and Technical Support

1,3-Diallyltetrakis(trimethylsiloxy)disiloxane is available from Aladdin Scientific under SKU D942648. To place an order, visit the Aladdin Scientific website or contact your regional sales representative. Bulk quantities and custom packaging may be available upon request.

For technical inquiries regarding application protocols, compatibility with specific polymerization systems, or analytical data interpretation, contact the Aladdin Scientific technical support team. When submitting an inquiry, please reference the product SKU (D942648) and your specific experimental context to enable prompt and accurate assistance.

Returns and refunds are handled in accordance with Aladdin Scientific's standard returns policy. Please refer to the website or contact customer service for details on return eligibility and procedures.

Frequently asked questions

What is the primary use of 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane in polymer research?

It is primarily used as a bifunctional crosslinker or monomer in siloxane polymer synthesis. Its two allyl groups react with Si–H-functional polysiloxanes via platinum-catalyzed hydrosilylation to form crosslinked silicone elastomeric networks, and it can also serve as a precursor for thiol-ene and other click-chemistry-based functionalization.

How should 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane be stored to maintain reagent quality?

Store the compound in a tightly sealed container in a cool, dry, well-ventilated location away from heat, light, and strong oxidizing agents. For long-term storage, keeping the reagent under an inert atmosphere such as nitrogen or argon is recommended to prevent oxidation or moisture-induced degradation of the allyl groups.

Which analytical techniques can confirm the identity and purity of D942648?

Gas chromatography (GC) or GC-MS is typically used for purity determination. Structural identity can be confirmed by ¹H NMR (allyl proton signals ~5.0–6.0 ppm), ²⁹Si NMR, and IR spectroscopy (Si–O–Si bands ~1000–1100 cm⁻¹; C=C stretch ~1630 cm⁻¹). Always cross-reference results with the certificate of analysis provided with each lot.

Can 1,3-Diallyltetrakis(trimethylsiloxy)disiloxane be used in thiol-ene click chemistry?

Yes. The allyl groups on this compound are reactive toward thiol-ene radical additions, making it suitable as an ene component in thiol-ene click chemistry. This approach allows straightforward attachment of thiol-bearing molecules to the siloxane scaffold under UV or thermal initiation, enabling further diversification of the siloxane architecture.

References

1. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry. Wiley, 2000. (General reference for organosilicon chemistry and siloxane crosslinking.)
2. Marciniec, B. (Ed.) Hydrosilylation: A Comprehensive Review on Recent Advances. Springer, 2009. (Reference for platinum-catalyzed hydrosilylation of allyl-functional siloxanes.)
3. Hoyle, C. E.; Bowman, C. N. Thiol-Ene Click Chemistry. Angew. Chem. Int. Ed. 2010, 49, 1540–1573. (Reference for thiol-ene functionalization of allyl groups.) doi:10.1002/anie.200903924

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