939-23-1

Basic information

• Product Name: 4-Phenylpyridine
• Synonyms: TIMTEC-BB SBB008518;4-Aza-1,1'-biphenyl;4-phenyl-pyridin;p-Phenylpyridine;Pyridine, 4-phenyl-;4-PHENYLPYRIDINE;4-PYRIDYLBENZENE;4-AZABIPHENYL
• CAS NO: 939-23-1
• Molecular Formula: C₁₁H₉N
• Molecular Weight: 155.2
• EINECS: 213-357-4
• Product Categories: Pyridine;Pyridines derivates;C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 939-23-1.mol
• Article Data: 234

Chemical Properties

• Melting Point: 69-73 °C(lit.)
• Boiling Point: 274-275 °C(lit.)
• Flash Point: 111.1 °C
• Appearance: Light yellow to beige/Crystalline Powder
• Density: 1.1088 (rough estimate)
• Vapor Pressure: 0.00623mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: 5.45±0.10(Predicted)
• Water Solubility: SOLUBLE
• BRN: 110490
• CAS DataBase Reference: 4-Phenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylpyridine(939-23-1)
• EPA Substance Registry System: 4-Phenylpyridine(939-23-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UT7141000
• F: 10
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 939-23-1(Hazardous Substances Data)

Usage

Uses

4-Phenylpyridine is a useful synthetic intermediate. 4-Phenylpyridine has been shown to induce inhibition of mitochondrial respiration in mice.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 1702, 1956 DOI: 10.1021/ja01589a060Synthetic Communications, 21, p. 619, 1991 DOI: 10.1080/00397919108020828Tetrahedron Letters, 36, p. 5247, 1995 DOI: 10.1016/0040-4039(95)00983-J

Enzyme inhibitor

This substituted pyridine (FW = 155.20 g/mol; CAS 939-23-1; M.P. = 69- 73°C; B.P. = 274-275°C), which occurs naturally and is likewise a manmade pollutant, inhibits human placental aromatase, Ki = 0.36 μM, monoamine oxidase, and NADH dehydrogenase. 4-Phenylpyridine is also an effective inhibitor of mitochondrial complex I. Note that it both occurs naturally and is an environmental pollutant.

InChI:InChI=1/C11H9N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-9H

Upstream product

• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 2206-26-0 [D₃]acetonitrile 
• 110-86-1 pyridine 
• 591-51-5 phenyllithium 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 98-80-6 phenylboronic acid 
• 19524-06-2 4-bromopyridine hydrochloride 
• 75-05-8 acetonitrile 
• 67970-80-3 1-methyl-4-phenyl-2(1H)-pyridone 
• 591-50-4 iodobenzene 
• 59020-06-3 4-trimethylstannyl-pyridine 
• 108-86-1 bromobenzene 
• 124252-41-1 (pyridin-4-yl)tributyltin 

Downstream Products

• 219716-19-5 2-[(Dimethyl-phenyl-silanyl)-methyl]-4-phenyl-2H-pyridine-1-carboxylic acid methyl ester 
• 55-22-1 pyridine-4-carboxylic acid 
• 112403-46-0 2-Butyl-4-phenyl-2H-pyridine-1-carboxylic acid phenyl ester 
• 112403-47-1 2-(4-Chloro-butyl)-4-phenyl-2H-pyridine-1-carboxylic acid phenyl ester 
• 112403-48-2 2-(2-Ethoxycarbonyl-ethyl)-4-phenyl-2H-pyridine-1-carboxylic acid phenyl ester 
• 112403-49-3 2-(3-Ethoxycarbonyl-propyl)-4-phenyl-2H-pyridine-1-carboxylic acid phenyl ester 
• 6153-92-0 4,4'-diphenyl-2,2'-bipyridine 
• 52565-57-8 ethyl 4-phenylpyridine-2-carboxylate 
• 18714-16-4 4-phenyl-pyridine-2-carbonitrile 
• 93288-69-8 4-Phenyl-1-propa-1,2-dienyl-pyridinium; perchlorate 
• 237424-24-7 dichlorobis(4-phenylpyridine)palladium 
• 203523-62-0 4-(4'-Ph-C₅H₄N)-arachno-B₉H₁₃ 
• 203523-64-2 5-(4'-Ph-C₅H₄N)-arachno-B₉H₁₃ 

Relevant articles and documents

Re(VII) complex of N-fused tetraphenylporphyrin

By treatment of N-fused tetraphenylporphyrin rhenium(I) tricarbonyl complex with trimethylamine N-oxide, oxidation of the metal center proceeded to afford N-fused tetraphenylporphyrin rhenium(VII) trioxo complex, which was quite stable against air, light and heat. The Royal Society of Chemistry 2005.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles

A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.