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Merck
CN

323322

Trimethylphosphine

97%, liquid

Synonym(s):

PMe3

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About This Item

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

Trimethylphosphine, 97%

vapor pressure

7.24 psi ( 20 °C)

Quality Level

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

signalword

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

Eyeshields, Faceshields, Gloves

Regulatory Information

监管及禁止进口产品

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Related Content

Phosphine Ligand Application Guide


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)
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)



Global Trade Item Number

SKUGTIN
323322-25G04061826708491