Diethyl (1-cyanoethyl)phosphonate
Diethyl (1-cyanoethyl)phosphonate (CAS 29668-61-9), with the molecular formula CH3CH(CN)P(O)(OC2H5)2 and a molecular weight of 191.16, is a versatile reagent used in organic synthesis. It is particularly valuable for C-C bond formation and olefination reactions, notably through the Horner-Wadsworth-Emmons reaction. This compound facilitates the stereoselective synthesis of complex molecules, including pharmaceutical intermediates.
- IUPAC
- (1-Cyanoethyl)phosphonic acid diethyl ester,NSC 135193
Horner-Wadsworth-Emmons Olefination
Diethyl (1-cyanoethyl)phosphonate serves as a key reagent in the Horner-Wadsworth-Emmons olefination reaction, enabling the synthesis of various unsaturated compounds.
Preparation of Pharmaceutical Intermediates
This phosphonate is utilised in the preparation of diverse pharmaceutical intermediates, including sphingosine phosphate receptor agonists and HIV-1 reverse transcriptase inhibitors.
Stereoselective Synthesis
It facilitates the stereoselective preparation of cyano(trifluoromethyl)pentenenitriles and other complex molecules through alkylation and elimination reactions.
Synthesis of Antibacterial Agents
The compound is employed in the synthesis of novel antibacterial agents such as [(methylenepiperidinyl) or (methylenepyrrolidinyl)fluorophenyl]oxazolidinones.
| Molecular weight | 191.16 |
|---|---|
| Linear formula | CH3CH(CN)P(O)(OC2H5)2 |
| Assay | 97% |
| Boiling point | 140-141 °C/11 mmHg(lit.) |
| Density | 1.085 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.432(lit.) |
| Application | Reacant for:• Preparation of sphingosine phosphate receptor (S1P) agonists with N-cinnamyl-ß-alanine moiety1• Preparation of benzyl- and benzoyldimethylaminopyridinones as HIV-1 reverse transcriptase inhibitors2• Stereoselective preparation of cyano(trifluoromethyl)pentenenitriles via alkylation, followed by elimination reaction3• Synthesis of [(methylenepiperidinyl) or (methylenepyrrolidinyl)fluorophenyl]oxazolidinone antibacterial agents4• Horner-Wadsworth-Emmons olefination5 |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 113 °C / 235.4 °F |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Diethyl (1-cyanoethyl)phosphonate used for?
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Diethyl (1-cyanoethyl)phosphonate is primarily used as a reagent in organic synthesis, particularly for C-C bond formation and Horner-Wadsworth-Emmons olefination reactions to prepare various unsaturated compounds and complex intermediates for pharmaceuticals.
What are the CAS number and formula for Diethyl (1-cyanoethyl)phosphonate?
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The CAS number is 29668-61-9 and the linear formula is CH3CH(CN)P(O)(OC2H5)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Diethyl (1-cyanoethyl)phosphonate with an assay of 97%. This product is intended for research and synthesis purposes and is not represented as USP, BP, EP, or pharmaceutical grade.
What are the safety considerations when handling Diethyl (1-cyanoethyl)phosphonate?
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Diethyl (1-cyanoethyl)phosphonate is classified as a Warning substance, with hazards including skin irritation (H315), eye irritation (H319), and respiratory irritation (H335). Appropriate personal protective equipment, such as eyeshields, gloves, and suitable respirators, should be used. Handle in a well-ventilated area.
How is Diethyl (1-cyanoethyl)phosphonate shipped and exported?
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As a global supplier and exporter of fine chemicals, Tech Serve Solutions adheres to all relevant shipping regulations for hazardous materials, ensuring safe and compliant packing and export worldwide.
How can I request a sample or quote for Diethyl (1-cyanoethyl)phosphonate?
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To request a sample or a quote for Diethyl (1-cyanoethyl)phosphonate, please contact our sales team through the website or by telephone.
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