N-Formylpiperidine

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).[1] It has also been used to transfer the formyl group to a Grignard reagent:[2]

PhCH2CH2MgCl + C6H11NO → PhCH2CH2CHO
N-Formylpiperidine
Names
Preferred IUPAC name
Piperidine-1-carbaldehyde
Other names
1-Formylpiperidine
Identifiers
3D model (JSmol)
107697
ChemSpider
DrugBank
ECHA InfoCard 100.018.170
EC Number
  • 219-986-0
MeSH N-Formylpiperidine
RTECS number
  • TN0380000
UNII
UN number 2810
Properties
C6H11NO
Molar mass 113.160 g·mol−1
Density 1.019 g cm−3
Boiling point 222 °C (432 °F; 495 K)
Vapor pressure 0.01 kPa
Hazards
Xn
R-phrases (outdated) R21/22, R36/37/38
S-phrases (outdated) S26, S36/37
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
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 [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

In some formylation reaction of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.[3]

References
  1. Eric F. V. Scriven & Ramiah Murugan. "Pyridine and Pyridine Derivatives". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley. doi:10.1002/0471238961.1625180919031809.a01.pub2.
  2. George Andrew Olah and Massoud Arvanaghi. "Formyl Transfer to Grignard Reagents with N-Formylpiperidine: 3-Phenylpropionaldehyde". Organic Syntheses.; Collective Volume, 7, p. 451
  3. Lidija Bondarenko; Ina Dix; Heino Hinrichs; Henning Hopf (2004). "Cyclophanes. Part LII:1 Ethynyl[2.2]paracyclophanes – New Building Blocks for Molecular Scaffolding". Synthesis. 2004 (16): 2751–2759. doi:10.1055/s-2004-834872.
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