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752940

Sigma-Aldrich

(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:
176325-83-0
Molecular Weight:
115.11
MDL number:
MFCD17013403
UNSPSC Code:
12352000
PubChem Substance ID:
329766326
NACRES:
NA.22

form

liquid

concentration

0.5 M in THF

density

0.896 g/mL at 25 °C

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 Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cyanomethylenetrimethylphosphorane
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Cyanomethylenetrimethylphosphorane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2003)
Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
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Tetrahedron Letters, 41(2), 235-237 (2000)
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