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324116

Sigma-Aldrich

Trimethylphosphine solution

1.0 M in toluene

Synonym(s):

PMe3, Trimethylphosphorus

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About This Item

Linear Formula:
(CH3)3P
CAS Number:
594-09-2
Molecular Weight:
76.08
Beilstein/REAXYS Number:
969138
MDL number:
MFCD00008510
UNSPSC Code:
12352128
PubChem Substance ID:
24859424
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: ligand
reaction type: Mitsunobu Reaction
reagent type: ligand
reaction type: Wittig Reaction

concentration

1.0 M in toluene

density

0.854 g/mL at 25 °C

functional group

phosphine

SMILES string

CP(C)C

InChI

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

InChI key

YWWDBCBWQNCYNR-UHFFFAOYSA-N

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Application

Reagent used in Mitsunobu reaction; transformation of azides into carbamates, aziridines from azidoalcohols; iminophosphoranes and aza-Wittig reaction.

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Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-4.0 °F

flash_point_c

-20 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ6518
STBK4240
BCBB3812V
SHBC3834V
60496TM

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Nathalie Merceron et al.
Chemical communications (Cambridge, England), (19), 2250-2251 (2002-10-26)
C-Phosphanyl-C-chloroiminium salts formally react as phosphonio(amino)carbenes with tert-butyl isocyanide and trimethylphosphine, and as R2NC+ with vinyl ether and diisopropylamine.
Hughes, D. L.; Reamer, R. A. et al.
Journal of the American Chemical Society, 110, 6487-6487 (110)
Alessandro A Boezio et al.
The Journal of organic chemistry, 68(8), 3241-3245 (2003-04-12)
A new class of orthoacylimine-derived chiral auxiliaries has been synthesized and tested in the nucleophilic addition of organolithium reagents to imines. The precursors can be prepared by an aza-Wittig reaction between the corresponding orthoacyl azide and a variety of aldehydes
Raúl García-Rodríguez et al.
Journal of the American Chemical Society, 134(3), 1400-1403 (2012-01-10)
We outline a reaction pathway for the cleavage of the P═Se bond in trialkylphosphine selenide during the synthesis of CdSe nanocrystals. The reaction between cadmium carboxylate and trimethylphosphine selenide in the presence of an alcohol produces alkoxytrimethylphosphonium (2). Control experiments
G Simonneaux et al.
Biochimica et biophysica acta, 1038(2), 199-203 (1990-04-19)
1H-NMR saturation transfer spectroscopy and nuclear Overhauser effect (NOE) have been utilized to assign several heme resonances in the low-spin trimethyl phosphine complex of sperm whale metmyoglobin. The two methods permit the location of the heme methyl resonances and the
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