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N-Formylpiperidine

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N-Formylpiperidine
Skeletal formula of N-formylpiperidine
Names
Preferred IUPAC name Piperidine-1-carbaldehyde
Other names 1-Formylpiperidine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 107697
ChemSpider
DrugBank
ECHA InfoCard 100.018.170 Edit this at Wikidata
EC Number
  • 219-986-0
MeSH N-Formylpiperidine
PubChem CID
RTECS number
  • TN0380000
UNII
UN number 2810
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2Key: FEWLNYSYJNLUOO-UHFFFAOYSA-N
  • InChI=1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2Key: FEWLNYSYJNLUOO-UHFFFAOYAJ
SMILES
  • O=CN1CCCCC1
Properties
Chemical formula C6H11NO
Molar mass 113.160 g·mol
Density 1.019 g cm
Boiling point 222 °C (432 °F; 495 K)
Vapor pressure 0.01 kPa
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H311, H315, H319, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Flash point 102 °C (216 °F; 375 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

N-Formylpiperidine is an organic compound with the formula C6H11NO. It is the amide of formic acid and piperidine. It can be used as a polar aprotic solvent, with better hydrocarbon solubility than other amide solvents such as dimethylformamide (DMF). It has also been used to transfer the formyl group to a Grignard reagent:

PhCH2CH2MgCl + C6H11NO → PhCH2CH2CHO

In some formylation reaction of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.

References

  1. Eric F. V. Scriven & Ramiah Murugan (2005). "Pyridine and Pyridine Derivatives". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley. doi:10.1002/0471238961.1625180919031809.a01.pub2. ISBN 0471238961.
  2. George Andrew Olah and Massoud Arvanaghi. "Formyl Transfer to Grignard Reagents with N-Formylpiperidine: 3-Phenylpropionaldehyde". Organic Syntheses; Collected Volumes, vol. 7, p. 451.
  3. Lidija Bondarenko; Ina Dix; Heino Hinrichs; Henning Hopf (2004). "Cyclophanes. Part LII:1 Ethynylparacyclophanes – New Building Blocks for Molecular Scaffolding". Synthesis. 2004 (16): 2751–2759. doi:10.1055/s-2004-834872.
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