 | |
| 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 |
|
| MeSH | N-Formylpiperidine |
PubChem CID |
|
| RTECS number |
|
| UNII | |
| UN number | 2810 |
CompTox Dashboard (EPA) |
|
| |
| |
| 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 | |
| GHS labelling: | |
  | |
| Danger | |
| H302, H311, H315, H319, H335 | |
| 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) | |
| 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).
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
- ↑ 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.
- ↑ George Andrew Olah and Massoud Arvanaghi. "Formyl Transfer to Grignard Reagents with N-Formylpiperidine: 3-Phenylpropionaldehyde". Organic Syntheses.; Collective Volume, vol. 7, p. 451
- ↑ 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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