Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

Base Information

• Chemical Name: Ethyl 5-(2-phenyleth-1-ynyl)nicotinate
• CAS No.: 175203-65-3
• Molecular Formula: C16H13 N O2
• Molecular Weight: 251.285
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70381333
• Wikidata: Q82172104
• Mol file: 175203-65-3.mol

Synonyms:175203-65-3;ethyl 5-(2-phenyleth-1-ynyl)nicotinate;ethyl 5-(2-phenylethynyl)pyridine-3-carboxylate;Ethyl 5-(phenylethynyl)nicotinate;3-Pyridinecarboxylic acid, 5-(2-phenylethynyl)-, ethyl ester;5-phenylethynyl-nicotinic acid ethyl ester;Maybridge1_005055;Oprea1_175597;SCHEMBL834845;HMS555N17;DTXSID70381333;XYMCXALGLXBQPK-UHFFFAOYSA-N;CCG-41035;MFCD00173986;AKOS015908646;FT-0626105;Ethyl 5-(phenylethynyl)pyridine-3-carboxylate;SR-01000631139-1;3-Pyridinecarboxylicacid,5-(2-phenylethynyl)-,ethyl ester

Chemical Property of Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

Chemical Property:

• Vapor Pressure: 8.48E-07mmHg at 25°C
• Boiling Point: 405.9°Cat760mmHg
• Flash Point: 199.3°C
• PSA: 39.19000
• Density: 1.18g/cm³
• LogP: 2.65810
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 359

Purity/Quality:

98% ^*data from raw suppliers

ETHYL 5-(2-PHENYLETH-1-YNYL)NICOTINATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=CC(=C1)C#CC2=CC=CC=C2

Technology Process of Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

There total 2 articles about Ethyl 5-(2-phenyleth-1-ynyl)nicotinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7) + phenylacetylene (536-74-3) → 5-(2-phenylethynyl)-3-pyridinecarboxylic acid ethyl ester (175203-65-3)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In ethyl acetate; at 50 ℃; for 20h;

Reference yield:

5-aminonicotinic acid (24242-19-1) → 5-(2-phenylethynyl)-3-pyridinecarboxylic acid ethyl ester (175203-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 48 h / Inert atmosphere; Reflux

2: palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(l) iodide / acetonitrile / 16 h / Inert atmosphere; Reflux

With hydrogenchloride; copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In 1,4-dioxane; acetonitrile;

DOI:10.1021/acs.jmedchem.5b00279

Reference yield: 95.0%

5-(2-phenylethynyl)-3-pyridinecarboxylic acid ethyl ester (175203-65-3) → 5-(phenylethynyl)pyridine-3-carboxylic acid (175203-69-7)

Guidance literature:

5-(2-phenylethynyl)-3-pyridinecarboxylic acid ethyl ester; With methanol; sodium hydroxide; water; at 20 ℃; for 20h;

With hydrogenchloride; water; pH=4;

upstream raw materials:

ethyl 5-bromo-3-pyridinecarboxylate

phenylacetylene

5-aminonicotinic acid

Downstream raw materials:

(5-phenylethynyl-pyridin-3-yl)-methanol

5-phenylethynylpyridine-3-carbaldehyde

methyl (S)-3-amino-3-(5-phenethyl-3-pyridyl)propionate

methyl (S)-3-amino-3-(5-phenethynyl-3-pyridyl)propionate

Refernces

• 1、 -. "SULFOXIMINES AS KINASE INHIBITORS". Page/Page column 33. . Retrieved 2008/12/05.