46268-56-8

Basic information

• Product Name: 4-Phenylpyridine-3-carboxaldehyde
• Synonyms: 4-Phenylpyridine-3-carboxaldehyde;4-phenylnicotinaldehyde;4-Phenyl-pyridine-3-carbaldehyde
• CAS NO: 46268-56-8
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• Mol File: 46268-56-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 342.8±30.0 °C(Predicted)
• Appearance: /
• Density: 1.147±0.06 g/cm3(Predicted)
• PKA: 3.60±0.18(Predicted)
• CAS DataBase Reference: 4-Phenylpyridine-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylpyridine-3-carboxaldehyde(46268-56-8)
• EPA Substance Registry System: 4-Phenylpyridine-3-carboxaldehyde(46268-56-8)

Safety Data

• Hazardous Substances Data: 46268-56-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3061, 1983 DOI: 10.1021/jo00166a026

Upstream product

• 98-80-6 phenylboronic acid 
• 174496-99-2 ethyl 4-chloropyridine-3-carboxylate hydrochloride 
• 40541-76-2 Ethyl 4-phenylpyridine-3-carboxylate 
• 19524-06-2 4-bromopyridine hydrochloride 
• 154105-64-3 4-bromonicotinaldehyde 
• 110601-03-1 4-Phenyl-4H-pyridine-1-carboxylic acid phenyl ester 
• 110-86-1 pyridine 
• 90732-07-3 3-[1,3]Dioxolan-2-yl-4-phenyl-4H-pyridine-1-carboxylic acid phenyl ester 
• 5740-72-7 3-(ethylenedioxymethyl)pyridine 
• 98-86-2 acetophenone 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 68-12-2 N,N-dimethyl-formamide 
• 113118-78-8 phenyl 3-formyl-4-phenyl-4H-pyridine-1-carboxylate: 
• 591-50-4 iodobenzene 

Downstream Products

• 1491169-35-7 2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-phenylpyridin-3-yl)methylamino)acetonitrile 
• 1491169-20-0 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)acetamide 
• 1491169-21-1 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)propionamide 
• 1491169-22-2 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)cyclohexanecarboxamide 
• 1491169-23-3 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)benzamide 
• 1491169-24-4 N-(3,5-bis(trifluoromethyl)benzyl)-4-chloro-N-((4-phenylpyridin-3-yl)methyl)benzamide 
• 1491169-25-5 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)isonicotinamide 
• 1491169-26-6 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)furan-2-carboxamide 
• 1491169-27-7 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)furan-3-carboxamide 
• 1491169-28-8 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)thiophene-2-carboxamide 
• 1491169-29-9 N-(3,5-bis(trifluoromethyl)benzyl)-N-((4-phenylpyridin-3-yl)methyl)thiophene-3-carboxamide 
• 1491169-01-7 N-(3,5-bis(trifluoromethyl)benzyl)-1-(4-phenylpyridin-3-yl)methanamine 
• 1491271-34-1 (4-phenylpyridin-3-yl)methanamine 
• 86610-29-9 1-methyl-3-(3-oxobutyl)-4-phenylpyridinium iodide 

Relevant articles and documents

Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.

Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists

Given its role in the mediation of energy and glucose homeostasis, the G-protein-coupled bile acid receptor1 (TGR5) is considered a potential target for the treatment of type2 diabetes mellitus and other metabolic disorders. By thorough analysis of diverse structures of published TGR5 agonists, a hypothetical ligand-based pharmacophore model was built, and a new class of potent TGR5 agonists, based on the novel 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazole core, was discovered by rational design. Three distinct synthetic methods for constructing 4,5-dihydro-1,2,4-oxadiazoles and extensive structure-activity relationship studies are reported herein. Compound (R)-54n, the structure of which was determined by single-crystal X-ray diffraction and quantum chemical solid-state TDDFT-ECD calculations, showed the best potency, with an EC50 value of 1.4nM toward hTGR5. Its favorable properties invitro warrant further investigation.

Vilsmeier-Haack reaction of tertiary alcohols: Formation of functionalised pyridines and naphthyridines

Vilsmeier-Haack reaction of 2-arylpropan-2-ols proceeds with multiple iminoalkylations leading to the formation of conjugated iminium salts which on ammonium acetate-induced cyclisation afford 4-arylnicotinaldehydes in good yields. Tertiary alcohols derived from aliphatic or alicyclic ketones by the addition of methyl Grignard are converted into substituted pyridines and naphthyridines by the action of Vilsmeier's reagent in N,N-dimethylformamide followed by nucleophile-assisted cyclisation in the presence of ammonium acetate.