323322

Trimethylphosphine

97%

• Synonym(s): PMe₃
• Linear Formula: (CH₃)₃P
• CAS Number: 594-09-2
• Molecular Weight: 76.08
• Beilstein: 969138
• EC Number: 209-823-1
• MDL number: MFCD00008510
• UNSPSC Code: 12352128
• PubChem Substance ID: 24859357
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H315,H319,H335
• Precautionary Statements: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• 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