N-Formylpiperidine

N-Formylpiperidine
Names
Preferred IUPAC name
Piperidine-1-carbaldehyde
Other names
1-Formylpiperidine
Identifiers
2591-86-8 YesY
3D model (Jmol) Interactive image
107697
ChemSpider 16486 YesY
DrugBank DB04113 YesY
ECHA InfoCard 100.018.170
EC Number 219-986-0
MeSH N-Formylpiperidine
PubChem 17429
RTECS number TN0380000
UN number 2810
Properties
C6H11NO
Molar mass 113.16 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 R21/22, R36/37/38
S-phrases S26, S36/37
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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).
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Infobox references

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

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". Org. Synth.; Coll. Vol., 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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