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Key Documents

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:
Molecular Weight:
76.08
Beilstein:
969138
MDL number:
UNSPSC Code:
12352128
PubChem Substance ID:
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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Related Categories

Application

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

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Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-4.0 °F

Flash Point(C)

-20 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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.
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.
A Bondon et al.
Biochimica et biophysica acta, 914(3), 289-293 (1987-08-21)
Binding of trimethylphosphine to myoglobins and hemoglobins from a variety of sources has been examined by 1H-nuclear magnetic resonance. The hemoglobins exhibit two resonances at high field (approx. -3.5 ppm) which have been assigned to PMe3 bound to alpha or

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