415642
Ethyl phenylphosphinate
94%
Synonym(s):
Ethoxyphenylphosphine oxide, O-Ethyl phenylphosphinate, Phenylphosphinic acid ethyl ester
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About This Item
Linear Formula:
C6H5P(O)H(OC2H5)
CAS Number:
Molecular Weight:
170.15
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
94%
form
liquid
refractive index
n20/D 1.526 (lit.)
bp
94-95 °C/1 mmHg (lit.)
density
1.129 g/mL at 25 °C (lit.)
SMILES string
CCO[PH](=O)c1ccccc1
InChI
1S/C8H11O2P/c1-2-10-11(9)8-6-4-3-5-7-8/h3-7,11H,2H2,1H3
InChI key
UNUJZVUJPIOMGH-UHFFFAOYSA-N
General description
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
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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)
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.
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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