324116

Sigma-Aldrich

Trimethylphosphine solution

1.0 M in toluene

Synonym(s):
PMe3, Trimethylphosphorus
Linear Formula:
(CH3)3P
CAS Number:
Molecular Weight:
76.08
Beilstein/REAXYS Number:
969138
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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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Packaging

100 mL in Sure/Seal™

Application

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

Signal Word

Danger

Target Organs

Central nervous system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN1993 - class 3 - PG 2 - RQ - VP <= 110kPa - Flammable liquids, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

-4.0 °F

Flash Point(C)

-20 °C

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...
A Bondon et al.
Biochimica et biophysica acta, 872(1-2), 163-166 (1986-07-25)
A 31P-NMR study of trimethyl phosphine bound to the heme iron(II) atom in natural myoglobins, hemoglobins and synthetic porphyrin iron(II) shows that the iron-bound trimethylphosphine 31P chemical shifts are sensitive to the presence of globin:separated NMR signals can be observed...
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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