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Sigma-Aldrich

Trimethylphosphine solution

1.0 M in THF

Synonym(s):

PMe3, Trimethylphosphorus

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About This Item

Linear Formula:
(CH3)3P
CAS Number:
594-09-2
Molecular Weight:
76.08
Beilstein:
969138
MDL number:
MFCD00008510
UNSPSC Code:
12352128
PubChem Substance ID:
24859423
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: ligand
reaction type: Mitsunobu Reaction
reagent type: ligand
reaction type: Wittig Reaction

concentration

1.0 M in THF

density

0.872 g/mL at 25 °C

functional group

phosphine

SMILES string

CP(C)C

InChI

1S/C3H9P/c1-4(2)3/h1-3H3

InChI key

YWWDBCBWQNCYNR-UHFFFAOYSA-N

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General description

Trimethylphosphine is the reagent used in Mitsunobu reaction. It participates in the transformation of azides into carbamates, aziridines from azidoalcohols, iminophosphoranes and aza-Wittig reaction. Electron diffraction study of trimethylphosphine has been reported.

Application

Trimethylphosphine (PMe3) solution is the suitable reagent used in the synthesis of Fe/Te cluster type complex, Fe6Te8(PMe3)6. It may be employed as a probe to investigate the acid sites in Y-zeolite. It may be used for the synthesis of hexakis(trimethylphosphine)tris-μ-methylene-diruthenium(III).

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Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-22.0 °F - closed cup

Flash Point(C)

-30 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Acid sites in zeolite Y: a solid-state NMR and infrared study using trimethylphosphine as a probe molecule.
Lunsford JH, et al.
Journal of the American Chemical Society, 107(6), 1540-1547 (1985)
Electron diffraction study of the structure of trimethylphosphine.
Bartell LS and Brockway LO.
J. Chem. Phys., 32(2), 512-515 (1960)
Synthesis and x-ray crystal structures of hexakis (trimethylphosphine) tris-. mu.-methylene-diruthenium (III) and its mono-and dicationic derivatives.
Hursthouse MB, et al.
Journal of the American Chemical Society, 101(15), 4128-4139 (1979)
Effect of Diverse Ligands on the Course of a Molecules-to-Solids Process and Properties of Its Intermediates.
Steigerwald ML, et al.
Inorganic Chemistry, 33(15), 3389-3395 (1994)
Joey L Methot et al.
Organic letters, 5(22), 4223-4226 (2003-10-24)
[reaction: see text]. The intramolecular vinylogous Morita-Baylis-Hillman reaction was explored to access the central cyclopentane ring of FR182877. The reaction manifold and product distribution is strikingly solvent and substrate dependent.
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