Ethyl (diethoxymethyl)phosphinate
- CAS No.
- 65600-74-0
- Chemical Name:
- Ethyl (diethoxymethyl)phosphinate
- Synonyms
- Ethyl (diethoxymethyl)phosphinate;diethoxymethyl-ethoxy-oxophosphonium;(Diethoxymethyl)phosphinic acid ethyl ester;ethyl (diethoxyMethyl) hydrogenophosphinate;Phosphinic acid, (diethoxymethyl)-, ethyl ester;Phosphinic acid, P-(diethoxymethyl)-, ethyl ester
- CBNumber:
- CB52582477
- Molecular Formula:
- C7H17O4P
- Molecular Weight:
- 196.18
- MDL Number:
- MFCD00460154
- MOL File:
- 65600-74-0.mol
- MSDS File:
- SDS
| Boiling point | 224℃ |
|---|---|
| Flash point | 107℃ |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| Appearance | Colorless to light yellow Liquid |
| InChI | InChI=1S/C7H17O4P/c1-4-9-7(10-5-2)12(8)11-6-3/h7,12H,4-6H2,1-3H3 |
| InChIKey | PJXJOBPJYXVTDE-UHFFFAOYSA-N |
| SMILES | P(C(OCC)OCC)(OCC)=O |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H332-H335 |
| Precautionary statements | P261-P280-P305+P351+P338 |
Ethyl (diethoxymethyl)phosphinate price
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Matrix Scientific | 095001 | Ethyl (diethoxymethyl)phosphinate | 65600-74-0 | 250.00mg | $435 | 2026-05-18 | Buy |
| Matrix Scientific | 095001 | Ethyl (diethoxymethyl)phosphinate | 65600-74-0 | 1.00g | $975 | 2026-05-18 | Buy |
| aablocks | AA00EJQT | Ethyl (diethoxymethyl)phosphinate 97% | 65600-74-0 | 100mg | $51 | 2026-05-28 | Buy |
| aablocks | AA00EJQT | Ethyl (diethoxymethyl)phosphinate 97% | 65600-74-0 | 250mg | $85 | 2026-05-28 | Buy |
| ACHEMBLOCK | S86804 | Ethyl (diethoxymethyl)phosphinate 95% | 65600-74-0 | 1G | $215 | 2026-05-27 | Buy |
Ethyl (diethoxymethyl)phosphinate Chemical Properties, Uses, Production
Synthesis
122-51-0
65600-74-0
General procedure for the synthesis of ethyl (diethoxymethyl)phosphonate from triethyl orthoformate: 1. Synthesis of ethyl (diethoxymethyl)hypophosphite from methanesulfonic acid: under nitrogen protection, triethyl orthoformate (42.1 mL, 253 mmol, 2.1 eq.) was slowly added to a mixture of finely ground ammonium hypophosphite (10 g, 120 mmol, 1.0 eq.), toluene (50 mL), and ethanol (3.5 mL) that had been cooled to 0 °C. The slurry was inerted and maintained at a temperature of about 0 °C. The mixture was then purified by a liquid bath. The slurry was inerted and the temperature was maintained at about 0°C. Methane sulfonic acid (8.4 mL, 127 mmol, 1.05 eq.) was added dropwise over 4 minutes, taking care to control the reaction temperature below 10°C. After the slurry was stirred at 0 °C for 1 h, GC analysis showed 93% conversion of ethyl ester to the target product. After 2 hours of reaction, the reaction was quenched with saturated aqueous sodium bicarbonate (37 mL). The organic phase was separated and concentrated under reduced pressure to 40 °C to give a colorless liquid containing about 50% toluene (28.0 g, GC purity 95%, assayed content 51.2%). Ethyl (diethoxymethyl)hypophosphite was obtained (14.3 g, 73.1 mmol, 61% yield). 2. Scale-up to 2-L scale: Triethyl orthoformate (632 mL, 3.80 mol, 2.1 eq.) was added to a mixture of ammonium hypophosphite (150 g, 1.81 mol, 1.0 eq.), toluene (750 mL), and ethanol (75 mL) cooled to 0 °C under nitrogen protection. The slurry was inerted and the temperature was maintained at about 0°C. Methane sulfonic acid (126 mL, 1.90 mol, 1.05 eq.) was added dropwise over 8 minutes, controlling the temperature below 10°C. After the slurry was stirred at 0 °C for 1 h, GC analysis showed 90% conversion. After 1.5 hours of reaction, the reaction was quenched with saturated aqueous sodium bicarbonate (600 mL). The organic phase was separated and concentrated under reduced pressure to 40°C to give a colorless liquid containing about 65% toluene (579 g, 88% GC purity, 34.4% assay). Ethyl (diethoxymethyl)hypophosphite was obtained (199.2 g, 1.02 mol, 56% yield). 3. Scale-up to 500-L scale: Under nitrogen protection, triethyl orthoformate (133.6 kg, 901.4 mol, 2.1 eq.) was added to a mixture of ammonium hypophosphite (35.6 kg, 429.2 mol, 1.0 eq.), toluene (107 L), and ethanol (11 L) that had been cooled to 0 °C and vigorously stirred. The slurry was inerted and cooled to -0 °C while continuously purged with nitrogen to reduce oxidation by-products. Methane sulfonic acid (43.3 kg, 450.7 mol, 1.05 eq.) was added dropwise over 30 min, controlling the temperature below 10 °C. The slurry was stirred at 0 °C for 2.5 h. After stirring, the reaction was quenched with a mixture of sodium bicarbonate (14.4 kg, 171.7 mol, 0.4 eq.) and water (128 L) to control the temperature below 10 °C. The charge vessel was rinsed with 14 L of water and the reaction mixture was stirred vigorously for 10 minutes. The organic phase was separated and concentrated under reduced pressure to 1/3 of the original volume (82 L, density 0.991 kg/L, 81.3 kg, GC purity 89.6%, assay 61%). Ethyl (diethoxymethyl)hypophosphite was obtained (49.6 kg, 252.7 mol, 58.9% yield).
References
[1] European Journal of Organic Chemistry, 2009, # 34, p. 6048 - 6054
[2] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8987 - 8991
[3] Chemistry - A European Journal, 2008, vol. 14, # 20, p. 6049 - 6052
[4] Tetrahedron, 1999, vol. 55, # 3, p. 771 - 780
[5] Patent: WO2006/31180, 2006, A1. Location in patent: Page/Page column 3-5
Ethyl (diethoxymethyl)phosphinate Preparation Products And Raw materials
Raw materials
Preparation Products
Ethyl (diethoxymethyl)phosphinate Suppliers
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