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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:
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

Key Documents

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Product Name

Trimethylphosphine, 97%

InChI key

YWWDBCBWQNCYNR-UHFFFAOYSA-N

InChI

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

SMILES string

CP(C)C

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

Quality Level

200

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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.

pictograms

FlameExclamation mark
GHS02,GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBS8671
SHBS8977
SHBR6878
SHBR6879
SHBR6880

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Conversion of ketoximes to ketones with trimethylphosphine and 2, 2′-dipyridyl diselenide
Martin M, et al.
Tetrahedron Letters, 45(29), 5559-5561 (2004)
C- H Activation of Imines by Trimethylphosphine-Supported Iron Complexes and Their Reactivities
Camadanli S, et al.
Organometallics, 28(7), 2300-2310 (2009)
The synthetic-technical development of oseltamivir phosphate [TM="Tamiflu"]: A race against time
Abrecht S, et al.
Chimia, 61(3), 93-99 (2007)
One-pot conversion of azides to Boc-protected amines with trimethylphosphine and Boc-ON
Ariza X, et al.
Tetrahedron Letters, 39(49), 9101-9102 (1998)
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)
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