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Sigma-Aldrich

Ethyl phenylphosphinate

94%

Synonim(y):

Ethoxyphenylphosphine oxide, O-Ethyl phenylphosphinate, Phenylphosphinic acid ethyl ester

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About This Item

Wzór liniowy:
C6H5P(O)H(OC2H5)
Numer CAS:
2511-09-3
Masa cząsteczkowa:
170.15
Numer MDL:
MFCD11505905
Kod UNSPSC:
12352100
Identyfikator substancji w PubChem:
24866017
NACRES:
NA.22

Próba

94%

Postać

liquid

współczynnik refrakcji

n20/D 1.526 (lit.)

tw

94-95 °C/1 mmHg (lit.)

gęstość

1.129 g/mL at 25 °C (lit.)

ciąg SMILES

CCO[PH](=O)c1ccccc1

InChI

1S/C8H11O2P/c1-2-10-11(9)8-6-4-3-5-7-8/h3-7,11H,2H2,1H3

Klucz InChI

UNUJZVUJPIOMGH-UHFFFAOYSA-N

Opis ogólny

Ethyl phenylphosphinate is an organophosphorous compound. It undergoes regioselective Markovnikov addition reaction with terminal alkynes in the presence of palladium-1,2-bis(diphenylphosphino)ethane complex (catalyst). Ethyl phenylphosphinate is the photodecomposition product of Inezin (S-benzyl O-ethyl phenylphosphonothiolate) on the ultraviolet irradiation. It can be prepared by the reaction of phosphinic acid with ethyl chloroformate in the presence of pyridine. Its ethylation using ethyl trimethylsilyl phenylphosphonite or the corresponding trimethylstannyl ester has been described. Its free-radical addition to ethylene has been reported to proceed with the retention of configuration.

Zastosowanie

Ethyl phenylphosphinate may be used in the preparation of the following diethyl imidazol-2-yl-(amino) methylphosphonates and phosphinates:
  • imidazol-2-yl-methyl(N-butylamino)phosphonate diethyl ester
  • imidazol-2-yl-methyl(N-benzylamino)phosphonate diethyl ester
  • imidazol-2-yl-methyl(N-butylamino)phenylphosphinate ethyl ester
  • imidazol-2-yl-methyl(N-benzylamino)phenylphosphinate ethyl ester
This page may contain text that has been machine translated.

Kod klasy składowania

10 - Combustible liquids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

235.4 °F - closed cup

Temperatura zapłonu (°C)

113 °C - closed cup

Środki ochrony indywidualnej

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certyfikaty analizy (CoA)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Organophosphorus compounds. II. Ethyl phenylphosphinate.
Hewitt DG.
Australian Journal of Chemistry, 32(2), 463-464 (1979)
Satish Kumar Nune et al.
Chemical communications (Cambridge, England), (27)(27), 2858-2860 (2007-07-05)
Palladium-1,2-bis(diphenylphosphino)ethane complex catalyses regioselective Markovnikov addition of ethyl phenylphosphinate to terminal alkynes in toluene, while the use of tri-tert-butylphosphine as the ligand or ethanol as the solvent leads to regioselectivity reversal.
Preparation of new imidazol-2-yl-(amino) methylphosphonates, phosphinates and phosphine oxides and their unexpected cleavage under acidic conditions.
Boduszek B, et al.
Tetrahedron, 68(4), 1223-1229 (2012)
T Murai et al.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 11(2), 185-197 (1976-01-01)
The photodecomposition of Inezin (S-benzyl O-ethyl phenylphosphonothiolate) in n-hexane under the ultraviiolet irradiation was investigated by gas liquid chromatography, thin layer chromatography, mass spectrometry, and infrared spectroscopy. Two main steps of photodecomposition were observed at the initial stage of irradiation.
Stereochemistry of a Michaelis-Arbusov reaction: alkylation of optically active ethyl trimethylsilyl phenylphosphonite with retention of configuration.
Van den Berg GR, et al.
Journal of the Chemical Society. Chemical Communications, 12, 606-607 (1971)

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