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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:
969138
MDL number:
MFCD00008510
UNSPSC Code:
12352128
PubChem Substance ID:
24859424
NACRES:
NA.22

form

liquid

Quality Level

100

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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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.
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
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, 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
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