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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

Quality Level

100

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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

752940-5ML:4548173314983
752940-10ML:4548173314976
752940-VAR:
752940-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR1781
MKCR9368
MKCL4884
SHBK3551
SHBH6696

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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)
Junnan Tang et al.
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