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Thermo Scientific Chemicals
Diethyl benzylphosphonate, 99%
CAS: 1080-32-6 | C11H17O3P | 228.228 g/mol
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Catalog number A10645.18
also known as A10645-18
Price (EUR)
95,50
Each
Quantity:
50 g
Price (EUR)
95,50
Each
Chemical Identifiers
CAS1080-32-6
IUPAC Namediethyl benzylphosphonate
Molecular FormulaC11H17O3P
InChI KeyAIPRAPZUGUTQKX-UHFFFAOYSA-N
SMILESCCOP(=O)(CC1=CC=CC=C1)OCC
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Specifications
Specification Sheet
Specification SheetAssay (GC)≥98.5%
Appearance (Color)Clear colorless to pale yellow
Refractive Index1.4950-1.4980 @ 20?C
FormLiquid
Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs.
Solubility
Insoluble in water.
Notes
Stable under recommended storage conditions. Incompatible with oxidizing agents.
Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs.
Solubility
Insoluble in water.
Notes
Stable under recommended storage conditions. Incompatible with oxidizing agents.
RUO – Research Use Only
General References:
- Stefan Lis; Zbigniew Piskuła; Zbigniew Hnatejko. Spectroscopic studies of lanthanides complexes with diethyl benzylphosphonate and diethylphosphonoacetic acid. Journal of Alloys and Compounds. 2008, 451, (1-2),388-394
- Tekla Bottin-Strzalko; Jacqueline Seyden-Penne; Marie-Jose Pouet; Marie Paule Simonnin. Structural studies of carbanionic species formed from phosphonates: anions of diethyl benzyl- and cyanomethylphosphonates. J. Org. Chem. 1978, 43, (22),4346-4351
- Horner-Wadsworth-Emmons reaction (see Appendix 1) with aromatic aldehydes gives stilbenes, almost exclusively trans: J. Org. Chem., 30, 680 (1965); J. Am. Chem. Soc., 83, 1733 (1961); 96, 1459 (1974). NaH + 15-crown-5 in THF promotes reaction with aldehydes and ketones at room temperature in excellent yields: Synthesis, 117 (1981). Phase-transfer reaction with cinnamaldehydes, using tetra-n-butylammonium iodide and NaOH gives diarylbutadienes: Synthesis, 187 (1976).
- See also 15-Crown-5, A12265.