Ethyl 5-bromonicotinate

Base Information

• Chemical Name: Ethyl 5-bromonicotinate
• CAS No.: 20986-40-7
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.061
• Hs Code.: 29333990
• European Community (EC) Number: 674-614-8
• NSC Number: 363896
• DSSTox Substance ID: DTXSID10175197
• Nikkaji Number: J267.196D
• Wikidata: Q63398570
• Mol file: 20986-40-7.mol

Synonyms:Ethyl 5-bromonicotinate;20986-40-7;5-bromonicotinic acid ethyl ester;ethyl 5-bromopyridine-3-carboxylate;5-Bromo-3-pyridinecarboxylic Acid Ethyl Ester;ETHYL5-BROMONICOTINATE;3-PYRIDINECARBOXYLIC ACID, 5-BROMO-, ETHYL ESTER;Ethyl 5-Bromo-3-pyridinecarboxylate;MFCD00040366;5-Bromonicotinicacidethylester;ethyl-5-bromonicotinate;ETHYL 3-BROMO-5-PYRIDINECARBOXYLATE;Maybridge1_006079;3-bromo-5-pyridine-carboxylic acid ethyl ester;3-bromo-5-carboethoxypyridine;SCHEMBL158686;HMS558M07;DTXSID10175197;5-bromo nicotinic acid ethyl ester;5-bromo-nicotinic acid ethyl ester;Ethyl 5-bromonicotinate, AldrichCPR;CCG-41718;NSC363896;RB1029;STK784022;AKOS000265047;AB01806;AC-9471;CS-W002187;FS-2110;NSC 363896;NSC-363896;SY014061;A4556;AM20070270;E0866;FT-0626120;EN300-85750;3-bromo-5-pyridine carboxylic acid ethyl ester;Q-101230;SR-01000631772-1;Q63398570

Chemical Property of Ethyl 5-bromonicotinate

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0.0135mmHg at 25°C
• Melting Point: 39-42 °C
• Refractive Index: 1.544
• Boiling Point: 258.8 °C at 760 mmHg
• PKA: 0.94±0.20(Predicted)
• Flash Point: 110.3 °C
• PSA: 39.19000
• Density: 1.501 g/cm³
• LogP: 2.02080
• Storage Temp.: 0-10°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 5-Bromonicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-3637/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=CN=C1)Br
• Uses: Ethyl 5-bromonicotinate is used as a key starting material for the preparation of 5-bromonicotinic acid hydrazide via reaction with a hydrazine hydrate.

Technology Process of Ethyl 5-bromonicotinate

There total 11 articles about Ethyl 5-bromonicotinate 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: 99.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + ethanol (64-17-5) → ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With thionyl chloride; Reflux;

ethanol; for 2h; Reflux;

With sodium hydrogencarbonate; In dichloromethane; water; pH=8;

Reference yield: 88.0%

5-aminonicotinic acid (24242-19-1) + ethanol (64-17-5) → ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 48h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jmedchem.5b00279

Reference yield: 86.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + ethylamine (75-04-7,85404-22-4) → ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7)

Guidance literature:

With propane-1,3-diyl dinitrite; In tetrahydrofuran; at 90 ℃; for 0.333333h; under 12929 Torr; Flow reactor;

DOI:10.1021/acs.orglett.7b02231

upstream raw materials:

5-bromonicotinoyl chloride

ethanol

5-bromo-3-pyridinecarboxylic acid

3,5-dibromopyridine

Downstream raw materials:

3-bromo-5-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine

5-[6-((3-chlorophenyl)amino)pyrazin-2-yl]nicotinic acid ethyl ester

5-{6-[tert-butoxycarbonyl-(3-chlorophenyl)amino]pyrazin-2-yl}nicotinic acid

5-{6-[tert-butoxycarbonyl-(3-chloro-phenyl)-amino]-pyrazin-2-yl}-nicotinic acid ethyl ester

Refernces

• 1、 Arutla, Viswanath,Leal, Joseph,Liu, Xiaowei,Sokalingam, Sriram,Raleigh, Michael,Adaralegbe, Adejimi,Liu, Li,Pentel, Paul R.,Hecht, Sidney M.,Chang, Yung. "Prescreening of Nicotine Hapten Linkers in Vitro To Select Hapten-Conjugate Vaccine Candidates for Pharmacokinetic Evaluation in Vivo". . p. 286 - 298. Retrieved 2017/05/15.
• 2、 -. "METHODS OF RATIONAL NICOTINE HAPTEN DESIGN AND USES THEREOF". Paragraph 0080. . Retrieved 2017/01/19.