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

• 110-86-1 pyridine 
• 2684-02-8 benzenediazonium 
• 938-81-8 N-nitrosoacetanilide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 1483-72-3 diphenyliodonium chloride 
• 981-18-0 triphenyl(phenylazo)methane 
• 108-86-1 bromobenzene 
• 94-36-0 dibenzoyl peroxide 
• 591-50-4 iodobenzene 
• 10338-69-9 1,2,3,6-tetrahydro-4-phenylpyridine 
• 82126-20-3 1-ethoxycarbonyl-4-phenyl-1,4-dihydropyridine 
• 112921-55-8 3-bromo-4-pyridyl phenyl sulfoxide 
• 19524-06-2 4-bromopyridine hydrochloride 
• 98-80-6 phenylboronic acid 

Downstream Products

• 94821-56-4 C₂₅H₂₄N₂O⁽²⁺⁾*2ClO₄^(1-) 
• 55-22-1 pyridine-4-carboxylic acid 
• 65-85-0 benzoic acid 
• 54151-74-5 2-bromo-4-phenylpyridine 
• 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 

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).

Ligand-to-metal charge transfer of a pyridine surface complex on TiO2for selective dehydrogenative cross-coupling with benzene

Dehydrogenative cross-coupling (DCC) between pyridine and benzene proceeded selectively using a TiO2 photocatalyst under visible light irradiation at optimized concentrations of the substrates. Visible light induces ligand-to-metal charge transfer (LMCT) between pyridine and a TiO2 surface to give a pyridine radical cation, which produces a pyridyl radical by its deprotonation or oxidation of another pyridine molecule. The pyridyl radical attacks a benzene ring to form an sp2C-sp2C bond and a hydrogen atom is subsequently removed to complete DCC. Selective excitation of the pyridine LMCT complex in the presence of an excess amount of benzene would be the key for higher selectivity. This journal is