Ethyl 6-chloronicotinate

Base Information

• Chemical Name: Ethyl 6-chloronicotinate
• CAS No.: 49608-01-7
• Molecular Formula: C8H8ClNO2
• Molecular Weight: 185.61
• Hs Code.: 29339900
• European Community (EC) Number: 610-463-6
• DSSTox Substance ID: DTXSID60384090
• Nikkaji Number: J1.555.222K
• Wikidata: Q72473710
• Mol file: 49608-01-7.mol

Synonyms:2-Chloropyridine-5-carboxylicacid ethyl ester;6-Chloronicotinic acid ethyl ester;Ethyl 2-chloro-5-pyridinecarboxylate;Ethyl 6-chloro-3-nicotinate;Ethyl 6-chloro-3-pyridinecarboxylate;

Chemical Property of Ethyl 6-chloronicotinate

Chemical Property:

• Appearance/Colour: white crystal powder
• Melting Point: 26-30 °C(lit.)
• Refractive Index: 1.522
• Boiling Point: 249.207 °C at 760 mmHg
• PKA: -1.95±0.10(Predicted)
• Flash Point: 104.517 °C
• PSA: 39.19000
• Density: 1.246 g/cm³
• LogP: 1.91170
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 185.0243562
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

6-ChloronicotinicAcidEthylEster ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(C=C1)Cl
• Uses: Ethyl 6-chloronicotinate is a nicotinic acid derivative used in the preparation of potent H3 receptor antagonists. Ethyl 6-chloropyridine-3-carboxylate (Ethyl 6-chloronicotinate) may be used in the preparation of ethyl 5-{[5-(1H-benzimidazol-2-yl)pyridin-2-yl]ethynyl}pyridine-2-carboxylate by reacting with 2-[6-(ethynyl)pyridin-3-yl]-1H-benzimidazole under microwave irradiation.

Technology Process of Ethyl 6-chloronicotinate

There total 8 articles about Ethyl 6-chloronicotinate 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: 92.3%

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) + Triethyl orthoacetate (78-39-7) → 6-chloro-3-pyridinecarboxylic acid ethyl ester (49608-01-7)

Guidance literature:

In toluene;

Reference yield: 84.0%

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) + ethanol (64-17-5) → 6-chloro-3-pyridinecarboxylic acid ethyl ester (49608-01-7)

Guidance literature:

With sulfuric acid; Heating / reflux;

Reference yield: 48.0%

1-oxy-nicotinic acid ethyl ester (14906-63-9) → ethyl 2-chloronicotinate (1452-94-4) + 6-chloro-3-pyridinecarboxylic acid ethyl ester (49608-01-7)

Guidance literature:

With trichlorophosphate; for 5h; Yields of byproduct given; Heating;

upstream raw materials:

6-Chloronicotinoyl chloride

ethanol

6-Chloro-3-pyridinecarboxylic acid

1-oxy-nicotinic acid ethyl ester

Downstream raw materials:

Ethyl 6-(3,4,5-trimethoxyphenyl)nicotinate

ethyl 6-(4-tert butylphenyl)-ethynyl nicotinate

tazarotene

6-{4-[4-(indan-5-ylcarbamoyl)-phenyl]-piperazin-1-yl}-nicotinic acid ethyl ester

Refernces

• 1、 -. "2-(1H-pyrazol-3-yl) pyridine derivative as well as preparation method and application thereof". Paragraph 0071-0074. . Retrieved 2021/06/22.
• 2、 -. "NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND BENAMIDE COMPOUNDS AND DRUGS CONTAINING THE SAME". Example 113. . Retrieved 2010/01/31.