N-Formylpiperidine

N-Formylpiperidine
	Skeletal formula of N-formylpiperidine
Names
	Preferred IUPAC name Piperidine-1-carbaldehyde
	Other names 1-Formylpiperidine
Identifiers
CAS Number	2591-86-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	107697
ChemSpider	16486 ;
DrugBank	DB04113 ;
ECHA InfoCard	100.018.170
EC Number	219-986-0;
MeSH	N-Formylpiperidine
PubChem CID	17429;
RTECS number	TN0380000;
UNII	ZIQ29H6CZG ;
UN number	2810
CompTox Dashboard (EPA)	DTXSID8043941 ;
	InChI InChI=1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2 Key: FEWLNYSYJNLUOO-UHFFFAOYSA-N ; InChI=1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2 Key: FEWLNYSYJNLUOO-UHFFFAOYAJ;
	SMILES O=CN1CCCCC1;
Properties
Chemical formula	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:
Pictograms
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)	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 [77 °F], 100 kPa). verify (what is ?) 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; Collected Volumes, 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.

[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 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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References