Ethyl phenylphosphinate

Name: Ethyl phenylphosphinate
Brand: ALDRICH
Price: 78.1 USD
Availability: InStock

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:

2511-09-3

Molecular Weight:

170.15

MDL number:

MFCD11505905

UNSPSC Code:

12352100

PubChem Substance ID:

24866017

NACRES:

NA.22

Key Documents

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Quality Level

100

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

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1 of 4

This Item	543055	418080	365270
Sigma-Aldrich 415642 Ethyl phenylphosphinate	Sigma-Aldrich 543055 Ethyl 1-cyano-1-cyclopropanecarboxylate	Sigma-Aldrich 418080 Pentafluorophenyl diphenylphosphinate	Sigma-Aldrich 365270 Methyl α-bromophenylacetate
assay 94%	assay 96%	assay -	assay 97%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 200
density 1.129 g/mL at 25 °C (lit.)	density 1.077 g/mL at 25 °C (lit.)	density -	density 1.455 g/mL at 25 °C (lit.)
form liquid	form -	form solid	form liquid
bp 94-95 °C/1 mmHg (lit.)	bp 217 °C (lit.)	bp -	bp 113 °C/3 mmHg (lit.)
refractive index n20/D 1.526 (lit.)	refractive index n20/D 1.445 (lit.)	refractive index -	refractive index n20/D 1.553 (lit.)

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).[1] Ethyl phenylphosphinate is the photodecomposition product of Inezin (S-benzyl O-ethyl phenylphosphonothiolate) on the ultraviolet irradiation.[2] It can be prepared by the reaction of phosphinic acid with ethyl chloroformate in the presence of pyridine.[3] 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.[4]

Application

Ethyl phenylphosphinate may be used in the preparation of the following diethyl imidazol-2-yl-(amino) methylphosphonates and phosphinates:[5]

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Organophosphorus compounds. II. Ethyl phenylphosphinate.

Hewitt DG.

Australian Journal of Chemistry, 32(2), 463-464 (1979)

Palladium-catalysed regioselective addition reaction of ethyl phenylphosphinate with terminal acetylenes: ligand- and solvent-dependent regioselectivity.

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.

Chemical transformation of S-benzyl O-ethyl phenylphosphonothiolate (Inezin) by ultraviolet light.

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)

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)

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Ethyl phenylphosphinate