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(Trimethylphosphoranylidene)acetonitrile solution

0.5 M in THF

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Synonym(s):
CMMP, Cyanomethylenetrimethylphosphorane solution
Empirical Formula (Hill Notation):
C5H10NP
CAS Number:
Molecular Weight:
115.11
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

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This Item
431303L010000245585
Acetonitrile

L010000

Acetonitrile

form

liquid

form

liquid

form

liquid

form

liquid

density

0.896 g/mL at 25 °C

density

1.069 g/mL at 25 °C

density

0.786 g/mL at 25 °C (lit.)

density

0.904 g/mL at 25 °C

concentration

0.5 M in THF

concentration

≥50 wt. % in ethyl acetate

concentration

-

concentration

1.0 M in THF

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

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

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)
Junnan Tang et al.
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Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
Tsunoda T, et al.
Tetrahedron Letters, 41(2), 235-237 (2000)
Siomara Hernandez et al.
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