323322

Sigma-Aldrich

Trimethylphosphine

97%

Synonym(s):
PMe3
Linear Formula:
(CH3)3P
CAS Number:
Molecular Weight:
76.08
Beilstein/REAXYS Number:
969138
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

vapor pressure

7.24 psi ( 20 °C)

assay

97%

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

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1993BE 3 / PGII

WGK Germany

WGK 3

Flash Point(F)

-2.2 °F - closed cup

Flash Point(C)

-19 °C - closed cup

Hydrogenation of carbon dioxide catalyzed by ruthenium trimethylphosphine complexes: the accelerating effect of certain alcohols and amines
Munshi P, et al.
Journal of the American Chemical Society, 124(27), 7963-7971 (2002)
Synthesis of trifluoromethyl ketones by palladium-catalyzed cross-coupling reaction of phenyl trifluoroacetate with organoboron compounds
Kakino R, et al.
Bulletin of the Chemical Society of Japan, 74(2), 371-376 (2001)
Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate. Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates
Palacios F, et al.
Tetrahedron, 59(15), 2617-2623 (2003)
The synthetic-technical development of oseltamivir phosphate [TM="Tamiflu"]: A race against time
Abrecht S, et al.
Chimia, 61(3), 93-99 (2007)
C- H Activation of Imines by Trimethylphosphine-Supported Iron Complexes and Their Reactivities
Camadanli S, et al.
Organometallics, 28(7), 2300-2310 (2009)

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