Ethyl 5-hydroxynicotinate

Base Information

• Chemical Name: Ethyl 5-hydroxynicotinate
• CAS No.: 59288-38-9
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID30358682
• Wikidata: Q82139436
• ChEMBL ID: CHEMBL1867182
• Mol file: 59288-38-9.mol

Synonyms:ethyl 5-hydroxynicotinate;59288-38-9;5-Hydroxy-nicotinic acid ethyl ester;ethyl 5-hydroxypyridine-3-carboxylate;3-Pyridinecarboxylic acid, 5-hydroxy-, ethyl ester;Ethyl 5-hydroxy-3-pyridinecarboxylate;3-Pyridinecarboxylic acid,5-hydroxy-,ethyl ester;3-(Ethoxycarbonyl)-5-hydroxypyridine;5-hydroxy-3-pyridinecarboxylic acid ethyl ester;Oprea1_153880;MLS000777702;SCHEMBL1812268;CHEMBL1867182;DTXSID30358682;LFDNUOROKFFJLE-UHFFFAOYSA-N;HMS2747I03;AMY23495;MFCD00510027;STK524945;Ethyl 3-hydroxy-5-pyridinecarboxylate;AKOS005458450;ethyl 5-oxidanylpyridine-3-carboxylate;PS-5350;SB53009;SMR000414147;CS-0078680;FT-0687909;A832245;AJ-333/25022004;J-517616

Chemical Property of Ethyl 5-hydroxynicotinate

Chemical Property:

• Vapor Pressure: 3.61E-06mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 375.4 °C at 760 mmHg
• PKA: 8.48±0.10(Predicted)
• Flash Point: 180.8 °C
• PSA: 59.42000
• Density: 1.233 g/cm³
• LogP: 0.96390
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 167.058243149
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

98% ^*data from raw suppliers

Ethyl5-Hydroxynicotinate ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=CN=C1)O

Technology Process of Ethyl 5-hydroxynicotinate

There total 4 articles about Ethyl 5-hydroxynicotinate 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: 83.0%

5-hydroxynicotinic acid (27828-71-3) + ethanol (64-17-5) → ethyl 5-hydroxy-3-pyridinecarboxylate (59288-38-9)

Guidance literature:

With thionyl chloride; at 0 ℃; for 24h; Heating / reflux;

Reference yield: 73.0%

5-hydroxynicotinic acid (27828-71-3) → ethyl 5-hydroxy-3-pyridinecarboxylate (59288-38-9)

Guidance literature:

With sulfuric acid; In ethanol; at 95 - 100 ℃; for 18h;

DOI:10.15227/orgsyn.097.0139

Reference yield:

oxiranyl-methanol (556-52-5) + 5-chloro-nicotinic acid ethyl ester (20825-98-3) → ethyl 5-hydroxy-3-pyridinecarboxylate (59288-38-9)

Guidance literature:

With NaH; In N-methyl-acetamide;

upstream raw materials:

5-hydroxynicotinic acid

ethanol

oxiranyl-methanol

5-chloro-nicotinic acid ethyl ester

Downstream raw materials:

5-(benzyloxy)nicotinic acid

ethyl furo[3,2-b]pyridine-6-carboxylate

ethyl 5-hydroxy-6-iodo-3-pyridinecarboxylate

nooglutil

Refernces

• 1、 Harmata, Alexander S.,Harmat, Michael,Peng, Feng,Campos, Kevin. "From 5-hydroxynicotinic acid to nitrogenous (4+3)cycloadducts". . p. 139 - 156. Retrieved 2020/09/02.
• 2、 -. "Synthesis method for 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b] pyridine-6-carboxylic acid". Paragraph 0008; 0009. . Retrieved 2016/12/16.