Tetraethyl P-Xylylenediphosphonate
CAS4546-04-7
Tetraethyl p-xylylenediphosphonate (CAS 4546-04-7) is a bis-phosphonate Horner-Wadsworth-Emmons reagent carrying a diethyl phosphonate group on each benzylic carbon of p-xylene. With two equivalents of an aromatic aldehyde it builds 1,4-distyrylbenzene and oligo(p-phenylene vinylene) frameworks with predominantly E-configured double bonds. KingPharm supplies tetraethyl p-xylylenediphosphonate for research and manufacturing, with a batch-specific certificate of analysis.
- CAS No.
- 4546-04-7
- Formula
- C16H28O6P2
- Mol. weight
- 378.34 g/mol
- Appearance
- White Crystalline Powder
Product Description
Tetraethyl p-xylylenediphosphonate, also named 1,4-bis(diethoxyphosphorylmethyl)benzene, is a symmetrical bis-phosphonate used as a two-sided Horner-Wadsworth-Emmons (HWE) olefination reagent. It is a white to off-white crystalline solid with a melting point of about 76 °C.
Under basic conditions, each benzylic CH2 next to a phosphonate group is deprotonated to a stabilised carbanion, which adds to an aldehyde carbonyl. Elimination of diethyl phosphate then forms a C=C bond. Because both ends react, one molecule joins two aldehydes and gives a 1,4-distyrylbenzene core; with dialdehydes it can be used for HWE polycondensation to poly(p-phenylene vinylene) (PPV) type materials.
Compared with the corresponding Wittig bis-phosphonium salts, the HWE route generally gives higher E-selectivity, and the water-soluble phosphate by-product is removed by aqueous work-up instead of separating triphenylphosphine oxide. This matters for conjugated materials, where geometric purity and residual impurities affect optical and electronic properties.
When evaluating tetraethyl p-xylylenediphosphonate, buyers usually check the assay, the melting range, the content of mono-phosphonate and other Arbuzov-related by-products, the water content, and batch-to-batch consistency.
Chemical Specifications
Identifiers
| CAS number | 4546-04-7 |
|---|---|
| Product name | Tetraethyl P-Xylylenediphosphonate |
| Chinese name | 对苯二甲基二磷酸四乙酯 |
| IUPAC name | 1,4-bis(diethoxyphosphorylmethyl)benzene |
| Synonyms | Phosphonic acid, P,P'-[1,4-phenylenebis(methylene)]bis-, P,P,P',P'-tetraethyl ester; Phosphonic acid, (p-phenylenedimethylene)di-, tetraethyl ester Phosphonic acid, [1,4-phenylenebis(methylene)]bis-, tetraethyl ester; 1,4-Bis(diethoxyphosphinylmethyl)benzene; 1,4-Xylenebis(diethylphosphonate) |
| Chinese synonyms | 对二甲苯二磷酸四乙酯; 对二苄二亚磷酸四乙酯; 对亚二甲苯二磷酸四乙酯; 对苯二甲双膦酸四乙基酯; 对苯二甲基二磷酸四乙酯; [4-(二乙氧基磷酰甲基)-苄基]-磷酸二乙酯; [4-(二乙氧基磷酰甲基)-苄基]-磷酸二乙酯,对二甲苯二磷酸四乙酯; 1,4-二甲苯亚基双(二乙基膦酸酯) |
| Molecular formula | C16H28O6P2 |
| Molecular weight | 378.34 g/mol |
| EC number | 224-902-0 |
| MDL number | MFCD00671576 |
| PubChem CID | 78303 |
| InChIKey | XTKQUBKFKSHRPS-UHFFFAOYSA-N |
| SMILES | CCOP(=O)(CC1=CC=C(C=C1)CP(=O)(OCC)OCC)OCC |
Physical and chemical properties
| Appearance | White Crystalline Powder |
|---|---|
| Melting Point | 73.0-78.0 ( ℃ ) |
Applications
Tetraethyl p-xylylenediphosphonate is used as a bidirectional HWE reagent to introduce a p-phenylene divinylene unit into conjugated molecules and polymers.
Distyrylbenzene fluorophores
Double HWE olefination with substituted benzaldehydes gives 1,4-distyrylbenzene derivatives used as fluorescent dyes, optical brighteners and luminescent probes.
PPV oligomers and polymers
Stepwise coupling or HWE polycondensation with aromatic dialdehydes builds oligo- and poly(p-phenylene vinylene) materials for organic light-emitting and photovoltaic research.
Functional conjugated building blocks
Aldehydes bearing amino, pyridyl or long-chain groups are coupled to give self-assembling amphiphiles, ligands and sensor molecules with a rigid trans-stilbene core.
Quality Documentation
The following documents can be provided for Tetraethyl P-Xylylenediphosphonate to support technical evaluation and purchasing. Documents are issued for the specific grade and batch supplied.
-
Certificate of Analysis (COA) Batch-specific test results against the specification.
-
Safety Data Sheet (SDS) Hazard identification, safe handling, storage and transport information.
-
Product specification The release specification with test items, limits and methods.
-
Method of Analysis (MOA) Detailed analytical procedures for the test methods listed in the specification.
Packaging, Storage & Transport
| Storage Temp | 室温, 干燥通风，密闭容器 ( ℃ ) |
|---|---|
| Available pack sizes | 25 g, 100 g, 500 g, 1 kg, 10kg, 25kg |
Read the current safety data sheet before handling. Packaging can be adapted to the order quantity and destination.
Frequently Asked Questions
How does tetraethyl p-xylylenediphosphonate compare with a Wittig bis-phosphonium salt?
Both introduce a p-phenylene divinylene unit, but the HWE reagent generally gives higher E-selectivity, and its phosphate by-product is water-soluble, so purification avoids separating triphenylphosphine oxide.
What conditions are typically used for the olefination?
The reagent is usually deprotonated with a strong base such as sodium hydride or potassium tert-butoxide in an anhydrous solvent such as THF or DMF, then treated with at least two equivalents of aldehyde. Moisture should be excluded because it consumes the base.
How should tetraethyl p-xylylenediphosphonate be stored?
Keep the container tightly sealed in a dry place at room temperature, away from moisture.
What is the CAS number of Tetraethyl P-Xylylenediphosphonate?
The CAS Registry Number of Tetraethyl P-Xylylenediphosphonate is 4546-04-7. Tetraethyl P-Xylylenediphosphonate is also known as Phosphonic acid, P,P'-[1,4-phenylenebis(methylene)]bis-, P,P,P',P'-tetraethyl ester; Phosphonic acid, (p-phenylenedimethylene)di-, tetraethyl ester Phosphonic acid, [1,4-phenylenebis(methylene)]bis-, tetraethyl ester; 1,4-Bis(diethoxyphosphinylmethyl)benzene.
What is the molecular formula and molecular weight of Tetraethyl P-Xylylenediphosphonate?
The molecular formula of Tetraethyl P-Xylylenediphosphonate is C16H28O6P2, and its molecular weight is 378.34 g/mol.
What is Tetraethyl P-Xylylenediphosphonate used for?
Tetraethyl p-xylylenediphosphonate is used as a bidirectional HWE reagent to introduce a p-phenylene divinylene unit into conjugated molecules and polymers.
Which quality documents are available for Tetraethyl P-Xylylenediphosphonate?
The following documents are available for Tetraethyl P-Xylylenediphosphonate: Certificate of Analysis (COA); Safety Data Sheet (SDS); Product specification; Method of Analysis (MOA). Contact KingPharm to request the documents for a specific batch.
How can I request a quotation for Tetraethyl P-Xylylenediphosphonate?
Send an inquiry for Tetraethyl P-Xylylenediphosphonate (CAS 4546-04-7) with the required quantity, target specification, destination country and any documentation requirements. KingPharm will confirm availability, packaging, lead time and price.
Related Products
Request a Quote for Tetraethyl P-Xylylenediphosphonate
Tell us the required quantity, target specification, destination country and any documentation requirements. We will confirm availability, packaging, lead time and price.
Page last reviewed on by Leo Xiao.