| Identification | More | [Name]
Trimethylphosphine | [CAS]
594-09-2 | [Synonyms]
PHOSPHORUS TRIMETHYL
TRIMETHYLPHOSPHINE
(CH3)3P
Trimethyl-phosphane
Trimethylphosphorus
Trimethylphosphine solution
Trimethylphosphineminampouled
TrimethylphosphineSureSealbottlecolorlessliquid
Methyl phosphine
TRIMETHYLPHOSPHINE, 1.0M SOLUTION IN TOL UENE
TRIMETHYLPHOSPHINE, 1.0M SOLUTION IN TET RAHYDROFURAN
TRIMETHYLPHOSPHINE SOLUTION, ~1 M IN TOL UENE
TRIMETHYLPHOSPHINE SOLUTION, ~1 M IN THF
Trimethylphosphine,99%
Trimethylphosphine,min.99%
Trimethylphosphine,min.99%(Sure/Sealbottle)
Trimethylphosphine,min. 99% | [EINECS(EC#)]
209-823-1 | [Molecular Formula]
C3H9P | [MDL Number]
MFCD00008510 | [Molecular Weight]
76.08 | [MOL File]
594-09-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
-86 °C (lit.) | [Boiling point ]
38-40 °C (lit.) | [density ]
0.872 g/mL at 25 °C
| [vapor pressure ]
7.24 psi ( 20 °C)
| [refractive index ]
n20/D 1.428(lit.)
| [Fp ]
−4 °F
| [storage temp. ]
2-8°C
| [form ]
liquid | [color ]
colorless | [Specific Gravity]
0.748 | [Water Solubility ]
Soluble in water. | [Sensitive ]
Air & Moisture Sensitive | [BRN ]
969138 | [InChIKey]
YWWDBCBWQNCYNR-UHFFFAOYSA-N | [CAS DataBase Reference]
594-09-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Phosphine, trimethyl-(594-09-2) |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xn,Xi | [Risk Statements ]
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R63:Possible risk of harm to the unborn child.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R38:Irritating to the skin.
R17:Spontaneously flammable in air. | [Safety Statements ]
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S7/9:Keep container tightly closed and in a well-ventilated place .
S33:Take precautionary measures against static discharges . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [F ]
10-13-23 | [HazardClass ]
4.2 | [PackingGroup ]
I | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [Uses]
Trimethylphosphine (PMe3) is an electron-rich phosphine ligand used as a reagent in Mitsunobu reaction.
It can be used:
- In transformation of azides into carbamates; aziridines to azidoalcohols; and ketoximes to ketones with 2,2′-dipyridyl diselenide.
- In Aza-Wittig reaction;, C-H bond activation of imines; cross-coupling reactions.
- In the preparation of (cyanomethylene) trimethylphosphorane (CMMP) which is used as a reagent in Mitsunobu type reaction.
- As a reagent in the synthesis of ruthenium trimethylphosphine complexes, which in turn are used as catalysts for hydrogenation of CO2 to formic acid.
| [Definition]
ChEBI: Trimethylphosphine is a tertiary phosphine. | [General Description]
Trimethylphosphine is the reagent used in Mitsunobu reaction. It participates in the transformation of azides into carbamates, aziridines from azidoalcohols, iminophosphoranes and aza-Wittig reaction. Electron diffraction study of trimethylphosphine has been reported. | [Purification Methods]
All operations should be carried out in an efficient fume cupboard because it is flammable, toxic and has a foul odor. Distil trimethylphosphine at atmospheric pressure in a stream of dry N2 (apparatus should be held together with springs to avoid loss of gas from increased pressure in the system) and the distillate run into a solution of AgI in aqueous KI whereby the silver complex [Me3PAgI]4 separates steadily. Filter off the complex, wash it with saturated aqueous KI solution, then H2O and dry it in a vacuum desiccator over P2O5. The dry complex is heated in a flask (in a stream of dry N2) in an oil bath at 140o, when pure Me3P distils off (bath temperature can be raised up to 260o). The vapour pressure of Me3P at 20o is 466mm and the b is 37.8o [Thomas & Eriks Inorg Synth IX 59 1967]. Alternatively, freshly distilled Me3P (6g) is shaken with a solution of AgI (13.2g, 1.1mol) in saturated aqueous KI solution (50mL) for 2hours. A white solid, not wetted with H2O, separates rapidly. It is collected, washed with the KI solution, H2O, and dried [Mann et al. J Chem Soc 1829 1937]. The silver complex is stable if kept dry in the dark, in which state it can be kept indefinitely. Me3P can be generated from the complex when required. Store it under N2 in a sealed container. It has been distilled in a vacuum line at -78o in vacuo and condensed at -96o [IR and NMR: Crosbie & Sheldrick J Inorg Nucl Chem 31 3684 1969]. The pK2 2 by NMR was 8.80 [Silver & Lutz J Am Chem Soc 83 786 1961, pK2 5 8.65: Henderson & Strueuli J Am Chem Soc 82 5791 1960]. |
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