ДИЭТИЛ (ФЕНИЛОКСОМЕТИЛ) ФОСФОНАТ

Identification

Diethyl(phenyloxomethyl)phosphonate, diethylbenzoylphosphonate, CAS 3277-27-8) is an acylphosphonate, formula C11H15O4P. Synonyms: AURORAKA-1431, diethylbenzoylphosphonate, diethoxyphosphoryl(phenyl)methanone, benzoylphosphonic acid diethyl ether. The catalog classification section is phosphines.

Basic Attributes

• Molecular weight: 242.21
• Exact weight: 242.071
• NSC Number: 2669
• DSSTox ID: DTXSID30277506
• HS code: 2931900090
• PSA: 52.6
• XLogP3: 3.0929

Physico-chemical properties

• Density: 1.156 g/ml at 25 °C (lit.)
• Boiling point: 186 °C (lit.)
• Flash point: >230°F
• Refractive index: n20/D 1.508 (lit.)

Substance class and purpose

Diethylbenzoylphosphonate belongs to the class of acylphosphonates - compounds in which the carbonyl group is directly bonded to a pentavalent phosphorus atom bearing two ethoxy substituents. This structure combines the electrophilicity of the ketone with the electron-withdrawing properties of the phosphonate group, which makes acylphosphonates valuable reagents in the Abramov reaction and Horner-Wadsworth-Emmons modifications for building the C=C bond, as well as substrates for the preparation of α-hydroxyphosphonic acids by adding nucleophiles to the carbonyl group.

α-Hydroxyphosphonates and related derivatives derived from diethylbenzoylphosphonate have a wide range of biological activities and are used as herbicides and fungicides, and the acylphosphonate itself is used as a building block in organic synthesis and as a component of photoinitiator UV-curing systems, where the acylphosphonate group is involved in photochemical homolytic cleavage to form radicals.

In terms of chemical behavior, acylphosphonates are close to α-ketoesters, but the phosphonate group more strongly polarizes the carbonyl, increasing its electrophilicity and facilitating the addition of amines, alcohols and other nucleophiles; this property is used in the design of phosphorus-containing analogues of amino acids and peptidomimetics in medicinal chemistry.

Safety Information

• Transport codes: NONH (does not apply to dangerous goods for all modes of transport)
• WGK Germany: 3

Storage and transportation

Store in a tightly closed container in a cool, dry place, protected from direct light due to the photochemical activity of the acylphosphonate group. NONH transport status simplifies supply logistics. When working, use gloves and safety glasses, avoid prolonged exposure to UV radiation on the substance.

The NSC number 2669 secures the substance in the sample catalog of the US National Cancer Institute, the DSSTox identifier DTXSID30277506 is used in toxicological databases, the HS code 2931900090 determines the product group during customs clearance of reagent batches. The PSA values ​​of 52.6 and XLogP3 of 3.0929 reflect the combination of a polar carbonyl phosphonate group and a lipophilic aromatic substituent.