Triethyl 4-phosphonocrotonate, mixture of isomers
Triethyl 4-phosphonocrotonate, mixture of isomers (CAS: 10236-14-3) is an organophosphorus compound with the linear formula (C2H5O)2P(O)CH2CH=CHCO2C2H5 and a molecular weight of 250.23 g/mol. This reagent is primarily utilized in organic synthesis for C-C bond formation, particularly in olefination reactions via the Horner-Wadsworth-Emmons methodology. Its applications span the synthesis of complex molecules including pharmaceutical intermediates and natural products.
- IUPAC
- 4-(Diethoxyphosphinyl)-2-butenoic acid ethyl ester,4-Phosphonocrotonic acid triethyl ester
- Synonyms
- (C2H5O)2P(O)CH2CH=CHCO2C2H54-(Diethoxyphosphinyl)-2-butenoic acid ethyl ester4-Phosphonocrotonic acid triethyl ester
Intermediate in Complex Molecule Synthesis
Utilised in the stereoselective preparation of fragments for macrolide antibiotics such as aplyronine A, employing diastereoselective Nozaki-Hiyama-Kishi coupling reactions.
Synthesis of Bioactive Compounds
Serves as a key reactant in the synthesis of orally bioavailable GPR40 agonists and fluoroketone inhibitors of calcium-independent phospholipase A2 (iPLA2).
Reagent for Olefination
Acts as a Wittig-type reagent in the Horner-Wadsworth-Emmons reaction, facilitating the formation of carbon-carbon double bonds with high stereoselectivity.
Building Block for Pharmaceutical Research
Employed in the preparation of mGlu4R agonists and as a leaving group component in DNA polymerization studies.
| Molecular weight | 250.23 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH2CH=CHCO2C2H5 |
| Assay | 90% |
| Boiling point | 135 °C/0.4 mmHg(lit.) |
| Density | 1.128 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.455(lit.) |
| Application | Reactant for: • Iminodipropionic acid as a leaving group for DNA polymerization by HIV-1 reverse transcriptase1• Stereoselective preparation of C1-C19 fragment of macrolide antibiotic aplyronine A using diastereoselective Nozaki-Hiyama-Kishi coupling reactions2• Orally bioavailable GPR40 agonist synthesis3• Synthesis of fluoroketone inhibitors of group VIA calcium-independent phospholipase A24• Preaparation of mGlu4R agonists5• Dearomatizing cyclization of nicotinyl-substituted esters and ketones6 |
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) | 26-37/39 |
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 Triethyl 4-phosphonocrotonate used for?
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Triethyl 4-phosphonocrotonate (CAS: 10236-14-3) is a reagent used in organic synthesis, notably for C-C bond formation and olefination reactions (Horner-Wadsworth-Emmons). It serves as a building block in the synthesis of complex molecules, including pharmaceutical intermediates and bioactive compounds.
What are the CAS number and formula for Triethyl 4-phosphonocrotonate?
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The CAS number is 10236-14-3. The linear formula is (C2H5O)2P(O)CH2CH=CHCO2C2H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Triethyl 4-phosphonocrotonate with an assay of 90%. This is typically considered a technical or research grade. TSS does not represent this product as USP, BP, or EP grade.
How should Triethyl 4-phosphonocrotonate be handled safely?
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This compound is a Warning substance, classified with H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Appropriate personal protective equipment, including eyeshields, gloves, and respiratory protection (e.g., ABEK respirator filter), should be used when handling. Ensure good ventilation.
Is this chemical controlled or scheduled?
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The provided data does not indicate that Triethyl 4-phosphonocrotonate is a controlled or scheduled substance.
How can I request a quote or sample?
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To request a quote or a sample of Triethyl 4-phosphonocrotonate, please contact the Tech Serve Solutions sales department via our website or direct inquiry channels.
How is this chemical packed and shipped?
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While specific packing details vary, Tech Serve Solutions exports fine chemicals globally. Standard industry packaging is used to ensure safe transport and compliance with international shipping regulations.
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