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N-Formylpiperidine: Difference between revisions

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Revision as of 22:46, 16 March 2011 edit87.188.185.234 (talk) dab link← Previous edit Latest revision as of 20:03, 27 December 2022 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Piperidines; added Category:1-Piperidinyl compounds using HotCat 
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{{DISPLAYTITLE:''N''-Formylpiperidine}} {{DISPLAYTITLE:''N''-Formylpiperidine}}

{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 400319633 | verifiedrevid = 419200108
| Name = ''N''-Formylpiperidine | Name = ''N''-Formylpiperidine
| ImageFile = N-Formylpiperidine.png | ImageFile = N-Formylpiperidine.png
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 121 | ImageSize = 121
| ImageName = Skeletal formula of N-formylpiperidine | ImageName = Skeletal formula of N-formylpiperidine
| PIN = Piperidine-1-carbaldehyde
| SystematicName = Piperidine-1-carbaldehyde<ref>{{Cite web|title = ''N''-Formylpiperidine - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=17429&loc=ec_rcs|work = The PubChem Project|location= USA|publisher = National Center for Biotechnology Information}}</ref>
| OtherNames = 1-Formylpiperidine | OtherNames = 1-Formylpiperidine
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2591-86-8
| PubChem = 17429 | CASNo = 2591-86-8
| Beilstein = 107697
| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
| ChemSpiderID = 16486 | PubChem = 17429
| ChemSpiderID = 16486
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 219-986-0
| UNNumber = 2810 | EINECS = 219-986-0
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04113
| MeSHName = N-Formylpiperidine | DrugBank = DB04113
| MeSHName = N-Formylpiperidine
| RTECS = TN0380000 | RTECS = TN0380000
| Beilstein = 107697 | UNNumber = 2810
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = O=CN1CCCCC1
| UNII = ZIQ29H6CZG
⚫ | StdInChI = 1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
⚫ | SMILES = O=CN1CCCCC1
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2 | StdInChI = 1S/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = FEWLNYSYJNLUOO-UHFFFAOYSA-N
⚫ | InChI = 1/C6H11NO/c8-6-7-4-2-1-3-5-7/h6H,1-5H2
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = FEWLNYSYJNLUOO-UHFFFAOYAJ | StdInChIKey = FEWLNYSYJNLUOO-UHFFFAOYSA-N
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChIKey = FEWLNYSYJNLUOO-UHFFFAOYAJ
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 6 | C=6 | H=11 | N=1 | O=1
⚫ | Density = 1.019 g cm<sup>−3</sup>
| H = 11
| N = 1 | BoilingPtC = 222
⚫ | VaporPressure = 0.01 kPa
| O = 1
| ExactMass = 113.084063979 g mol<sup>-1</sup>
⚫ | Density = 1.019 g cm<sup>-3</sup>
| BoilingPtC = 222
⚫ | VaporPressure = 0.01 kPa
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| EUClass = {{Hazchem Xn}} | GHSPictograms = {{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| RPhrases = {{R21/22}}, {{R36/37/38}}
| HPhrases = {{H-phrases|302|311|315|319|335}}
| SPhrases = {{S26}}, {{S36/37}}
| 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-H = 2
| NFPA-R = 0 | NFPA-F = 1
| FlashPt = 102 °C | NFPA-R = 0
| FlashPtC = 102
}} }}
}} }}


'''''N''-Formylpiperidine''' is an organic compound with the formula C<sub>6</sub>H<sub>11</sub>NO. It is the amide of ] and ]. It can be used as a ], with better hydrocarbon solubility than other amide solvents such as ] (DMF).<ref>{{cite book |title=Kirk‑Othmer Encyclopedia of Chemical Technology |chapter=Pyridine and Pyridine Derivatives |author=Eric F. V. Scriven and Ramiah Murugan |publisher=Wiley |doi=10.1002/0471238961.1625180919031809.a01.pub2}}</ref> It has also been used to transfer the formyl group to a ]:<ref>{{OrgSynth | collvol = 7 | collvolpages = 451 | prep = cv7p0451 | title = Formyl Transfer to Grignard Reagents with ''N''-Formylpiperidine: 3-Phenylpropionaldehyde | author = ] and Massoud Arvanaghi}}</ref> '''''N''-Formylpiperidine''' is an organic compound with the formula C<sub>6</sub>H<sub>11</sub>NO. It is the amide of ] and ]. It can be used as a ], with better hydrocarbon solubility than other amide solvents such as ] (DMF).<ref>{{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 }}</ref> It has also been used to transfer the formyl group to a ]:<ref>{{OrgSynth | collvol = 7 | collvolpages = 451 | prep = cv7p0451 | title = Formyl Transfer to Grignard Reagents with ''N''-Formylpiperidine: 3-Phenylpropionaldehyde | author = ] and Massoud Arvanaghi}}</ref>


: PhCH<sub>2</sub>CH<sub>2</sub>MgCl + C<sub>6</sub>H<sub>11</sub>NO &rarr; PhCH<sub>2</sub>CH<sub>2</sub>CHO : PhCH<sub>2</sub>CH<sub>2</sub>MgCl + C<sub>6</sub>H<sub>11</sub>NO → PhCH<sub>2</sub>CH<sub>2</sub>CHO


In some ] of alkyllithium compounds, ''N''-formylpiperidine gives higher yields than the DMF.<ref>>{{cite journal | author = Lidija Bondarenko, Ina Dix, Heino Hinrichs, Henning Hopf | title = Cyclophanes. Part LII:1 Ethynylparacyclophanes – New Building Blocks for Molecular Scaffolding | journal = ] | volume = 2004| issue = 16 | pages = 2751–2759 | year = 2004 | doi = 10.1055/s-2004-834872}}</ref> In some ] of alkyllithium compounds, ''N''-formylpiperidine gives higher yields than the DMF.<ref>{{cite journal |author1=Lidija Bondarenko |author2=Ina Dix |author3=Heino Hinrichs |author4=Henning Hopf | title = Cyclophanes. Part LII:1 Ethynylparacyclophanes&nbsp;– New Building Blocks for Molecular Scaffolding | journal = ] | volume = 2004| issue = 16 | pages = 2751–2759 | year = 2004 | doi = 10.1055/s-2004-834872}}</ref>


==References== ==References==
{{reflist}}
<references/>


{{DEFAULTSORT:Formylpiperidine, N-}} {{DEFAULTSORT:Formylpiperidine, N-}}
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