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323322

Sigma-Aldrich

Trimethylphosphine

97%

Synonym(s):
PMe3
Linear Formula:
(CH3)3P
CAS Number:
Molecular Weight:
76.08
Beilstein:
969138
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

vapor pressure

7.24 psi ( 20 °C)

assay

97%

form

liquid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Mitsunobu Reaction

reagent type: ligand
reaction type: Wittig Reaction

refractive index

n20/D 1.428 (lit.)

bp

38-40 °C (lit.)

mp

−86 °C (lit.)

density

0.738 g/mL at 20 °C (lit.)

functional group

phosphine

storage temp.

2-8°C

SMILES string

CP(C)C

InChI

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

InChI key

YWWDBCBWQNCYNR-UHFFFAOYSA-N

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Application

Trimethylphosphine (PMe3) is an electron-rich phosphine ligand used as a reagent in Mitsunobu reaction.
It can be used:
  • In transformation of azides into carbamates; aziridines to azidoalcohols; and ketoximes to ketones with 2,2′-dipyridyl diselenide.
  • In Aza-Wittig reaction;, C-H bond activation of imines; cross-coupling reactions.
  • In the preparation of (cyanomethylene) trimethylphosphorane (CMMP) which is used as a reagent in Mitsunobu type reaction.
  • As a reagent in the synthesis of ruthenium trimethylphosphine complexes, which in turn are used as catalysts for hydrogenation of CO2 to formic acid.

Packaging

25 g in Sure/Seal™

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-2.2 °F - closed cup

Flash Point(C)

-19 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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