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323322

Trimethylphosphine

97%, liquid

Synonym(s):

PMe3

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About This Item

Linear Formula:
(CH3)3P
CAS Number:
594-09-2
Molecular Weight:
76.08
NACRES:
NA.22
PubChem Substance ID:
24859357
UNSPSC Code:
12352128
EC Number:
209-823-1
MDL number:
MFCD00008510
Beilstein/REAXYS Number:
969138
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Product Name

Trimethylphosphine, 97%

vapor pressure

7.24 psi ( 20 °C)

Quality Segment

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

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class

3 - Flammable liquids

WGK

WGK 3

Flash Point (°F)

-2.2 °F - closed cup

Flash Point (°C)

-19 °C - closed cup

PPE (personal protective equipment)

Eyeshields, Faceshields, Gloves

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