10177-13-6

Basic information

• Product Name: METHYL 5-PHENYLNICOTINATE
• Synonyms: AKOS BAR-1624;METHYL 5-PHENYLNICOTINATE;METHYL-5-PHENYL-NICOTONOATE
• CAS NO: 10177-13-6
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• Mol File: 10177-13-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 356°Cat760mmHg
• Flash Point: 169.1°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 5-PHENYLNICOTINATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-PHENYLNICOTINATE(10177-13-6)
• EPA Substance Registry System: METHYL 5-PHENYLNICOTINATE(10177-13-6)

Safety Data

• Hazardous Substances Data: 10177-13-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045

InChI:InChI=1/C13H11NO2/c1-16-13(15)12-7-11(8-14-9-12)10-5-3-2-4-6-10/h2-9H,1H3

Upstream product

• 29681-44-5 5-bromo-3-pyridine carboxylic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 36052-25-2 5-amino-nicotinic acid methyl ester 
• 591-50-4 iodobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 39620-02-5 5-bromonicotinoyl chloride 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 59-67-6 nicotinic acid 

Downstream Products

• 885274-99-7 1-[(tert-butoxy)carbonyl]-5-phenylpiperidine-3-carboxylic acid 
• 187392-96-7 3-hydroxymethyl-5-phenyl-pyridine 

Relevant articles and documents

Fast and efficient access to a family of multifunctional 1,3,5-trisubstituted piperidines

A collection of new 1,3,5-trisubstituted piperidines has been synthesized starting from the commercially available 5-bromonicotinic acid. A unified, diastereoselective strategy allows the controlled access to both cis and trans stereochemistries. The heterocyclic compounds thus prepared bear multiple functional groups suitable for structural diversification and combichem protocols. Copyright Taylor & Francis Group, LLC.

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A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by other methods, can be easily obtained with this metal-free transformation. Moreover, this transformation can be followed by Suzuki-Miyaura cross-coupling without purification of the borylation products, which enhances the practical usefulness of this method. A possible reaction mechanism involving radical species has been proposed.