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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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signalword

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
STBK4240
BCBB3812V
SHBC3834V
60496TM
BCBB3812

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Hughes, D. L.; Reamer, R. A. et al.
Journal of the American Chemical Society, 110, 6487-6487 (110)
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.
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
Joey L Methot et al.
Organic letters, 5(22), 4223-4226 (2003-10-24)
[reaction: see text]. The intramolecular vinylogous Morita-Baylis-Hillman reaction was explored to access the central cyclopentane ring of FR182877. The reaction manifold and product distribution is strikingly solvent and substrate dependent.
William Levason et al.
Dalton transactions (Cambridge, England : 2003), 43(25), 9557-9566 (2014-05-16)
The reactions of the soft diphosphines o-C6H4(PMe2)2, Me2P(CH2)2PMe2, Et2P(CH2)2PEt2 or o-C6H4(PPh2)2 with NbF5 or TaF5 in anhydrous MeCN solution produce [MF4(diphosphine)2][MF6] (M = Nb or Ta), which have been characterised by microanalysis, IR, (1)H, (19)F{(1)H}, (31)P{(1)H} and (93)Nb NMR spectroscopy.
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