752940
(Trimethylphosphoranylidene)acetonitrile solution
0.5 M in THF
Synonym(s):
CMMP, Cyanomethylenetrimethylphosphorane solution
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About This Item
Empirical Formula (Hill Notation):
C5H10NP
CAS Number:
Molecular Weight:
115.11
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
liquid
concentration
0.5 M in THF
density
0.896 g/mL at 25 °C
functional group
nitrile
phosphine
storage temp.
2-8°C
SMILES string
CP(C)(C)=CC#N
InChI
1S/C5H10NP/c1-7(2,3)5-4-6/h5H,1-3H3
InChI key
KJFJIEHJCVSAKJ-UHFFFAOYSA-N
General description
(Trimethylphosphoranylidene)acetonitrile is a reagent generally employed in the Wittig olefination of less reactive carboxylic acid compounds like esters, N-Boc lactams, lactones, and imides to give α,β-unsaturated nitriles. It is also used as an alternate reagent for Mitsonobu reaction by replacing DEAD/PPh3 for the alkylation of C-H and N-H bonds.
Other Notes
If precipitate is observed, warm gently to resolubilize
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
Target Organs
Respiratory system
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
-5.8 °F - closed cup
Flash Point(C)
-21.0 °C - closed cup
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Cyanomethylenetrimethylphosphorane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2003)
Cyanomethylenetrimethylphosphorane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2003)
Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
Tsunoda T, et al.
Tetrahedron Letters, 41(2), 235-237 (2000)
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