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415642 Sigma-Aldrich

Ethyl phenylphosphinate

94%

  • CAS Number 2511-09-3

  • Linear Formula C6H5P(O)H(OC2H5)

  • Molecular Weight 170.15

  •  MDL number MFCD11505905

  •  PubChem Substance ID 24866017

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Organic Building Blocks, Phosphonates/Phosphinates, Phosphorus Compounds More...
Quality Level   100
assay   94%
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

Description

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

Packaging

5, 25 mL in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
SZ5600000
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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