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Triethylphosphine

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Triethylphosphine
Names
Preferred IUPAC name Triethylphosphane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.245 Edit this at Wikidata
EC Number
  • 209-068-8
Gmelin Reference 2485
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H15P/c1-4-7(5-2)6-3/h4-6H2,1-3H3Key: RXJKFRMDXUJTEX-UHFFFAOYSA-N
SMILES
  • CCP(CC)CC
Properties
Chemical formula C6H15P
Molar mass 118.160 g·mol
Appearance colorless liquid
Density 0.802 g/cm
Boiling point 127–128 °C (261–262 °F; 400–401 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H224, H225, H250, H314
Precautionary statements P210, P222, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P422, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Triethylphosphine is the organophosphorus compound with the formula P(CH2CH3)3, commonly abbreviated as PEt3. It is a colorless liquid with an unpleasant odor characteristic of alkylphosphines. The compound is a common ligand in organometallic chemistry, such as in auranofin.

Structure and simple reactions

It is a pyramidal molecule with approximate C3v symmetry.

PEt3 is usually prepared using Grignard reagents:

3 CH3CH2MgCl + P(OC6H5)3 → P(CH2CH3)3 + 3 C6H5OMgCl

PEt3 reacts with strong acids to give salts X. This reaction is reversible. Similarly, it is also easily alkylated to give phosphonium derivatives. PEt3 is easily oxidised to the phosphine oxide with oxygen.

Coordination chemistry

Triethylphosphine is a highly basic ligand that forms coordination complexes with many metals. As a ligand, triethylphosphine's Tolman cone angle is 132°. Being a relatively compact phosphine, several can bind to a single transition metal, as illustrated by the existence of Pt(PEt3)4. As a phosphine ligand, triethylphosphine gained acceptance earlier than did the simpler trimethylphosphine, as illustrated by the preparation of the hydride complex trans-PtHCl(PEt3)2.

Structure of Pt(PEt3)4.

Safety

PEt3 is toxic. It converts to a low toxicity phosphine oxide upon treatment with sodium hypochlorite or hydrogen peroxide.

References

  1. Bruckmann, J.; Krüger, C. (1995). "Trimethylphosphine and Triethylphosphine in the Solid State". Acta Crystallogr. C. 51 (6): 1155–1158. Bibcode:1995AcCrC..51.1155B. doi:10.1107/S0108270194014368.
  2. Annette Schier and Hubert Schmidbaur "P-Donor Ligands" in Encyclopedia of Inorganic Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/0470862106.ia177
  3. G. L. Miessler and D. A. Tarr Inorganic Chemistry, 3rd Ed, Pearson/Prentice Hall publisher, ISBN 0-13-035471-6.
  4. Yoshida, T.; Matsuda, T.; Otsuka, S. (1990). "Tetrakis(Triethylphosphine)Platinum(0)". Inorganic Syntheses. Vol. 28. p. 122. doi:10.1002/9780470132593.ch32. ISBN 978-0-470-13259-3.
  5. Joseph Chatt (1968). "Hydride Complexes". Science. 160 (3829): 723–729. Bibcode:1968Sci...160..723C. doi:10.1126/science.160.3829.723. PMID 17784306. S2CID 22350909.
  6. Pospiech, S.; Bolte, M.; Lerner, H.-W.; Wagner, M. (2014). "Insertion Reactions into the Boron–Boron Bonds of Barrelene-Type 1,2-Diaminodiboranes(4)". Organometallics. 33 (23): 6967–6974. doi:10.1021/om501087u.
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