ChemicalBook > CAS DataBase List > ETHYL (DIETHOXYMETHYL)PHOSPHINATE

ETHYL (DIETHOXYMETHYL)PHOSPHINATE

Product Name: 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
Formula Weight: 196.18
MOL File: 65600-74-0.mol

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ETHYL (DIETHOXYMETHYL)PHOSPHINATE Property

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

AK Scientific

Product number: 0060AC
Product name: Ethyl(diethoxymethyl)phosphinate
Packaging: 250mg
Price: $135
Updated: 2021/12/16

Matrix Scientific

Product number: 095001
Product name: Ethyl (diethoxymethyl)phosphinate
Purity: 95+%
Packaging: 250mg
Price: $435
Updated: 2021/12/16

Ark Pharm

Product number: AK101523
Product name: Ethyl(diethoxymethyl)phosphinate
Purity: 95+%
Packaging: 5g
Price: $555
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0079361
Product name: ETHYL (DIETHOXYMETHYL)PHOSPHINATE
Purity: 95.00%
Packaging: 5G
Price: $909.56
Updated: 2021/12/16

Matrix Scientific

Product number: 095001
Product name: Ethyl (diethoxymethyl)phosphinate
Purity: 95+%
Packaging: 1g
Price: $975
Updated: 2021/12/16

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ETHYL (DIETHOXYMETHYL)PHOSPHINATE Chemical Properties,Usage,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

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65600-74-0, ETHYL (DIETHOXYMETHYL)PHOSPHINATERelated Search:

DIETHYL PHOSPHATE ETHYL (METHYLTHIO)ACETATE

ETHYL (DIETHOXYMETHYL)PHOSPHINATE

ethyl (diethoxyMethyl) hydrogenophosphinate

(Diethoxymethyl)phosphinic acid ethyl ester

Phosphinic acid, (diethoxymethyl)-, ethyl ester

diethoxymethyl-ethoxy-oxophosphonium

Phosphinic acid, P-(diethoxymethyl)-, ethyl ester

65600-74-0