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415642

Sigma-Aldrich

Ethyl phenylphosphinate

94%

Synonyme(s) :

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

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About This Item

Formule linéaire :
C6H5P(O)H(OC2H5)
Numéro CAS:
2511-09-3
Poids moléculaire :
170.15
Numéro MDL:
MFCD11505905
Code UNSPSC :
12352100
ID de substance PubChem :
24866017
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

94%

Forme

liquid

Indice de réfraction

n20/D 1.526 (lit.)

Point d'ébullition

94-95 °C/1 mmHg (lit.)

Densité

1.129 g/mL at 25 °C (lit.)

Chaîne 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

Clé InChI

UNUJZVUJPIOMGH-UHFFFAOYSA-N

Description générale

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.

Application

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

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

235.4 °F - closed cup

Point d'éclair (°C)

113 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCS9345
MKCN5235
MKCN0262
MKCC6599
MKBW4101V

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Consulter la Bibliothèque de documents

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.
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.
Organophosphorus compounds. II. Ethyl phenylphosphinate.
Hewitt DG.
Australian Journal of Chemistry, 32(2), 463-464 (1979)
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)
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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