N-Formylpiperidine

N-Formylpiperidine
Systematic name Piperidine-1-carbaldehyde[1]
Other names 1-Formylpiperidine
Identifiers
CAS number	2591-86-8
PubChem	17429
ChemSpider	16486 Y
EC number	219-986-0
UN number	2810
DrugBank	DB04113
MeSH	N-Formylpiperidine
RTECS number	TN0380000
Beilstein Reference	107697
Jmol-3D images	Image 1
SMILES O=CN1CCCCC1
InChI InChI=1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2 Y Key: FEWLNYSYJNLUOO-UHFFFAOYSA-N Y InChI=1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2 Key: FEWLNYSYJNLUOO-UHFFFAOYAJ
Properties
Molecular formula	C6H11NO
Molar mass	113.16 g mol−1
Exact mass	113.084063979 g mol-1
Density	1.019 g cm-3
Boiling point	222 °C, 495 K, 432 °F
Vapor pressure	0.01 kPa
Hazards
EU classification	Xn
R-phrases	R21/22, R36/37/38
S-phrases	S26, S36/37
NFPA 704	1 2 0
Flash point	102 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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).^[2] It has also been used to transfer the formyl group to a Grignard reagent:^[3]

PhCH₂CH₂MgCl + C₆H₁₁NO → PhCH₂CH₂CHO

In some formylation reaction of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.^[4]

References

1. ^ "N-Formylpiperidine - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=17429&loc=ec_rcs. 
2. ^ Eric F. V. Scriven and Ramiah Murugan. "Pyridine and Pyridine Derivatives". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley. doi:10.1002/0471238961.1625180919031809.a01.pub2. 
3. ^ George Andrew Olah and Massoud Arvanaghi, "Formyl Transfer to Grignard Reagents with N-Formylpiperidine: 3-Phenylpropionaldehyde", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0451 ; Coll. Vol. 7: 451 
4. ^ >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.