N-Formylpiperidine

Base Information

• Chemical Name: N-Formylpiperidine
• CAS No.: 2591-86-8
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 29333999
• European Community (EC) Number: 219-986-0
• NSC Number: 404158,1066
• UNII: ZIQ29H6CZG
• DSSTox Substance ID: DTXSID8043941
• Nikkaji Number: J77.422G
• Wikipedia: N-Formylpiperidine
• Wikidata: Q6951369
• Metabolomics Workbench ID: 45045
• ChEMBL ID: CHEMBL1232817
• Mol file: 2591-86-8.mol

Synonyms:N-formylpiperidine

Chemical Property of N-Formylpiperidine

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 0.1 mm Hg ( 25 °C)
• Melting Point: -31 °C
• Refractive Index: n20/D 1.484(lit.)
• Boiling Point: 222.5 °C at 760 mmHg
• PKA: -0.44±0.20(Predicted)
• Flash Point: 91.7 °C
• PSA: 20.31000
• Density: 1.087 g/cm³
• LogP: 1.20250
• Storage Temp.: Store below +30°C.
• Water Solubility.: freely soluble
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 76.6

Purity/Quality:

99.9% ^*data from raw suppliers

Formylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xn,Xi
• Statements: 21/22-36/37/38
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)C=O
• Description: This simple piperidine base has recently been discovered in the oxygenated fraction from Piper nigrum. The structure has been elucidated from chemical and spectroscopic data.
• Uses: Solvent for polar and nonpolar compounds, as well as many high polymers; gas absorption; plastics modifiers. Reactant for: Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoateVilsmeier-type reactions of pyrazoles with amides in the presence of phosphorous oxychlorideCO-free aminocarbonylation of N-substituted formamides with aryl iodides/bromides catalyzed by palladium acetate and Xantphos for synthesis of arylamidesSynthesis of alternating copolymers for organic photovoltaic applicationsOne-pot double functionalization of π-deficient heterocyclic lithium reagentsSynthesis of thermally stable piezofluorochromic aggregation-induced emission compounds

Technology Process of N-Formylpiperidine

There total 129 articles about N-Formylpiperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1-phenyl-2-piperidin-1-yl-ethanone (779-52-2) → N-Formylpiperidine (2591-86-8) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With dihydrogen peroxide; In ethanol;

DOI:10.1039/c39830000392

Reference yield: 92.0%

1-(4-methoxy-phenyl)-2-piperidino-ethanone (80354-61-6) → N-Formylpiperidine (2591-86-8) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With dihydrogen peroxide; In ethanol;

DOI:10.1039/c39830000392

Reference yield: 67.0%

Bis(1-piperidinyl)acetonitril (4637-29-0) + benzaldehyde (100-52-7) → N-Formylpiperidine (2591-86-8) + 2-phenyl-2-piperidinoacetonitrile (5766-79-0)

Guidance literature:

at 80 ℃; for 36h;

upstream raw materials:

piperidine

formic acid

chloral hydrate

ethanol

Downstream raw materials:

1-(1-cyclohexen-1-ylmethyl)-1-piperidine

1-(cyclohexylmethyl)piperidine

fluorene-9-carbaldehyde

3,4-dimethoxy-benzaldehyde

Refernces

• 1、 Yang, Zhenzhen,Wang, Huan,Ji, Guipeng,Yu, Xiaoxiao,Chen, Yu,Liu, Xinwei,Wu, Cailing,Liu, Zhimin. "Pyridine-functionalized organic porous polymers: applications in efficient CO2 adsorption and conversion". . p. 2869 - 2872. Retrieved 2017.
• 2、 Nefedov,Slinkin,Kucherov,Sergeeva,Eidus. "Carbonylation of piperidine with carbon monoxide in the presence of CuNaA-zeolite catalyst". . p. 2037 - 2038. Retrieved 1975.
• 3、 Motokura, Ken,Takahashi, Naoki,Miyaji, Akimitsu,Sakamoto, Yasuharu,Yamaguchi, Sho,Baba, Toshihide. "Mechanistic studies on the N-formylation of amines with CO2 and hydrosilane catalyzed by a Cu-diphosphine complex". . p. 6951 - 6956. Retrieved 2014.
• 4、 Rasu, Loorthuraja,Rennie, Ben,Miskolzie, Mark,Bergens, Steven H.. "A Fortuitous, Mild Catalytic Carbon-Carbon Bond Hydrogenolysis by a Phosphine-Free Catalyst". . p. 561 - 564. Retrieved 2016.
• 5、 Nefedov et al.. "-". . . Retrieved 1975.
• 6、 Sternberg et al.. "-". . p. 3148,3151. Retrieved 1953.
• 7、 Nefedov et al.. "-". . . Retrieved 1974.
• 8、 Nefedov et al.. "-". . . Retrieved 1974.
• 9、 Hassan Tolba, Amal,Krupi?ka, Martin,Chudoba, Josef,Cibulka, Radek. "Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative". supporting information. p. 6825 - 6830. Retrieved 2021/09/11.
• 10、 Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao. "Nickel-Catalyzed Amination of Aryl Chlorides with Amides". supporting information. p. 687 - 691. Retrieved 2021/01/09.