3466-80-6

Basic information

• Product Name: 2-PHENYLPIPERIDINE
• Synonyms: ART-CHEM-BB B022867;AKOS BB-9267;AKOS B022867;2-PHENYLPIPERIDINE;2-PHENYL-PIPERIDINE >98%;(Piperidin-2-yl)benzene;2-Phenylpiperidine(WX604287)
• CAS NO: 3466-80-6
• Molecular Formula: C₁₁H₁₅N
• Molecular Weight: 161.24
• EINECS: 222-422-6
• Product Categories: Piperidine
• Mol File: 3466-80-6.mol
• Article Data: 77

Chemical Properties

• Melting Point: 18 °C
• Boiling Point: 70-72°C/0.45mm
• Flash Point: 110.96 °C
• Appearance: /
• Density: 0.967 g/cm³
• Vapor Pressure: 0.0147mmHg at 25°C
• Refractive Index: 1.5390 to 1.5430
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.74±0.10(Predicted)
• CAS DataBase Reference: 2-PHENYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLPIPERIDINE(3466-80-6)
• EPA Substance Registry System: 2-PHENYLPIPERIDINE(3466-80-6)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 23-24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 3466-80-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Synthesis Reference(s)

Synthetic Communications, 25, p. 3789, 1995 DOI: 10.1080/00397919508011452Chemical and Pharmaceutical Bulletin, 43, p. 1422, 1995 DOI: 10.1248/cpb.43.1422

InChI:InChI=1/C11H15N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-3,6-7,11-12H,4-5,8-9H2

Upstream product

• 30091-51-1 5-benzoyl-2-phenylpyridine 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 109-72-8 n-butyllithium 
• 108-86-1 bromobenzene 
• 2156-71-0 N-chloropiperidine 
• 591-51-5 phenyllithium 
• 951408-28-9 5,5-difluoro-6-phenyl-2,3,4,5-tetrahydropyridine 
• 1452523-62-4 (2R)-1-[(R)-2-methylpropane-2-sulfinyl]-2-phenylpiperidine 
• 5259-98-3 5-chloropentan-1-ol 
• 100-58-3 phenylmagnesium bromide 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 116437-42-4 (5-oxo-5-phenyl-pentyl)-carbamic acid tert-butyl ester 
• 830319-73-8 1-(2-bromobenzenesulfonyl)piperidin-2-one 
• 830319-75-0 1-(2-bromo-benzenesulfonyl)-piperidin-2-ol 

Downstream Products

• 1086420-42-9 2-(2-phenylpiperidin-1-yl)-1H-benzoimidazole 
• 154874-89-2 tert-butyl 2-phenylipiperidine-1-carboxylate 
• 1364780-88-0 C₁₆H₂₂LiNO₂ 
• 1364781-69-0 tert-butyl 2-butyl-2-phenylpiperidine-1-carboxylate 
• 1364781-74-7 tert-butyl 2-(methoxymethyl)-2-phenylpiperidine-1-carboxylate 
• 1364781-79-2 tert-butyl 2-(3-methylbut-2-enyl)-2-phenylpiperidine-1-carboxylate 
• 1364781-95-2 1-tert-butyl 2-methyl 2-phenylpiperidine-1,2-dicarboxylate 
• 1364782-99-9 (2S)-tert-butyl 2-methyl-2-phenylpiperidine-1-carboxylate 
• 1364783-04-9 C₁₂H₁₇N 
• 1364783-09-4 tert-butyl 2-(methoxymethyl)-2-phenylpiperidine-1-carboxylate 
• 3466-80-6 (R)-(+)-6-phenylpiperidine 
• 176650-38-7 2-phenyl-1-(toluene-4-sulfonyl)-piperidine 
• 100127-88-6 2-phenyl-3,4,5,6-tetrahydropyridine-N-oxide 

Relevant articles and documents

Rapid Synthesis of α-Chiral Piperidines via a Highly Diastereoselective Continuous Flow Protocol

A practical continuous flow protocol has been developed using readily accessible N-(tert-butylsulfinyl)-bromoimine and Grignard reagents, providing various functionalized piperidines (34 examples) in superior results (typically >80% yield and with >90:10 dr) within minutes. The high-performance scale-up is smoothly carried out, and efficient synthesis of the drug precursor further showcases its utility. This flow process offers rapid and scalable access to enantioenriched α-substituted piperidines.

Borane-Catalyzed Reduction of Pyridines via a Hydroboration/Hydrogenation Cascade

We have developed a method for a B(C6F5)3-catalyzed hydroboration/hydrogenation cascade reduction of pyridines. The method was particularly effective for 2,3-disubstituted pyridines, which generated piperidines in high yields with high cis selectivity. Mechanistic studies indicated that the pyridine substrates and the piperidine products sequentially acted as bases in cooperation with B(C6F5)3to split H2. The broad functional group tolerance of the method allowed its use for the synthesis of some biologically active molecules.

H2 Activation by Non-Transition-Metal Systems: Hydrogenation of Aldimines and Ketimines with LiN(SiMe3)2

In recent years, H2 activation at non-transition-metal centers has met with increasing attention. Here, a system in which H2 is activated and transferred to aldimines and ketimines using substoichiometric amounts of lithium bis(trimethylsilyl)amide is reported. Notably, the reaction tolerates the presence of acidic protons in the α-position. Mechanistic investigations indicated that the reaction proceeds via a lithium hydride intermediate as the actual reductant.