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A10645 Diethyl benzylphosphonate, 99%

CAS Number
1080-32-6
Synonyms
Benzylphosphonic acid diethyl ester
Diethyl alpha-toluenephosphonate

Stock No. Size Price ($) Quantity Availability
A10645-18 50g 72.70
A10645-30 250g 337.00
A10645-0B 1000g 1153.00
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Diethyl benzylphosphonate, 99%

MDL
MFCD00009078
EINECS
214-097-4

Chemical Properties

Formula
C11H17O3P
Formula Weight
228.23
Boiling Point
106-108°/1mm
Flash Point
>110°(230°F)
Density
1.094
Refractive Index
1.4975
Storage & Sensitivity
Ambient temperatures.
Solubility
Insoluble in water.

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.

Notes

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
2580931
Harmonized Tariff Code
2931.39
TSCA
Yes
RTECS
SZ6600000

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