N-Formylpiperidine
{{DISPLAYTITLE:N-Formylpiperidine}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 419200108
| Name = N-Formylpiperidine
| ImageFile = N-Formylpiperidine.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 121
| ImageName = Skeletal formula of N-formylpiperidine
| PIN = Piperidine-1-carbaldehyde
| OtherNames = 1-Formylpiperidine
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2591-86-8
| Beilstein = 107697
| PubChem = 17429
| ChemSpiderID = 16486
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 219-986-0
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04113
| MeSHName = N-Formylpiperidine
| RTECS = TN0380000
| UNNumber = 2810
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZIQ29H6CZG
| SMILES = O=CN1CCCCC1
| StdInChI = 1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
| StdInChIKey = FEWLNYSYJNLUOO-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = FEWLNYSYJNLUOO-UHFFFAOYAJ
}}
|Section2={{Chembox Properties
| C=6 | H=11 | N=1 | O=1
| Density = 1.019 g cm−3
| BoilingPtC = 222
| VaporPressure = 0.01 kPa
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|311|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|322|330|332+313|337+313|361|362|363|403+233|405|501}}
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPtC = 102
}}
}}
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).{{cite book |title=Kirk‑Othmer Encyclopedia of Chemical Technology |chapter=Pyridine and Pyridine Derivatives |author1=Eric F. V. Scriven |author2=Ramiah Murugan |year=2005 |name-list-style=amp |publisher=Wiley |doi=10.1002/0471238961.1625180919031809.a01.pub2|isbn=0471238961 }} It has also been used to transfer the formyl group to a Grignard reagent:{{OrgSynth | collvol = 7 | collvolpages = 451 | prep = cv7p0451 | title = Formyl Transfer to Grignard Reagents with N-Formylpiperidine: 3-Phenylpropionaldehyde | author = George Andrew Olah and Massoud Arvanaghi}}
: PhCH2CH2MgCl + C6H11NO → PhCH2CH2CHO
In some formylation reaction of alkyllithium compounds, N-formylpiperidine gives higher yields than the DMF.{{cite journal |author1=Lidija Bondarenko |author2=Ina Dix |author3=Heino Hinrichs |author4=Henning Hopf | title = Cyclophanes. Part LII:1 Ethynyl[2.2]paracyclophanes – New Building Blocks for Molecular Scaffolding | journal = Synthesis | volume = 2004| issue = 16 | pages = 2751–2759 | year = 2004 | doi = 10.1055/s-2004-834872}}