Ethyl 2-chlorothiazole-4-carboxylate

Base Information

• Chemical Name: Ethyl 2-chlorothiazole-4-carboxylate
• CAS No.: 41731-52-6
• Molecular Formula: C6H6ClNO2S
• Molecular Weight: 191.638
• Hs Code.: 2934100090
• European Community (EC) Number: 869-792-0
• DSSTox Substance ID: DTXSID00518291
• Wikidata: Q72473839
• Mol file: 41731-52-6.mol

Synonyms:ethyl 2-chlorothiazole-4-carboxylate;41731-52-6;ethyl 2-chloro-1,3-thiazole-4-carboxylate;ethyl 2-chloro-4-thiazolecarboxylate;MFCD11045348;2-CHLOROTHIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;ethyl2-chlorothiazole-4-carboxylate;SCHEMBL691101;DTXSID00518291;GILVNZWYCBUGMT-UHFFFAOYSA-N;BCP26280;ethyl 2-chloro-4thiazolecarboxylate;AM9900;ethyl-2-chloro-4-thiazolecarboxylate;AKOS005258791;DS-13655;SY039949;A6867;CS-0006056;4-Thiazolecarboxylicacid,2-chloro-,ethyl ester;EN300-259523;2-Chloro-thiazole-4-carboxylic acid ethyl ester;AU-004/43508297;Ethyl 2-chlorothiazole-4-carboxylate, AldrichCPR;3-(n-methylpiperazine)-propyl-bromide dihydrobromide;J-520740

Chemical Property of Ethyl 2-chlorothiazole-4-carboxylate

Chemical Property:

• Boiling Point: 283.907 °C at 760 mmHg
• PKA: -1.50±0.10(Predicted)
• Flash Point: 125.503 °C
• PSA: 67.43000
• Density: 1.384 g/cm³
• LogP: 1.97320
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 190.9807773
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

98% ^*data from raw suppliers

Ethyl 2-chlorothiazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CSC(=N1)Cl

Technology Process of Ethyl 2-chlorothiazole-4-carboxylate

There total 4 articles about Ethyl 2-chlorothiazole-4-carboxylate 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: 74.0%

2-aminothiazole-4-carboxylate (5398-36-7) → 2-chloro-thiazole-4-carboxylic acid ethyl ester (41731-52-6)

Guidance literature:

With hydrogenchloride; copper(l) chloride; sodium nitrite; In water; at 20 ℃; for 2.16667h; Cooling with salt-ice;

Reference yield:

ethyl Bromopyruvate (70-23-5) → 2-chloro-thiazole-4-carboxylic acid ethyl ester (41731-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 1.5 h / 105 °C / Inert atmosphere

2: tert.-butylnitrite; copper dichloride / acetonitrile / 1 h / 65 °C / Inert atmosphere

With tert.-butylnitrite; copper dichloride; In ethanol; acetonitrile; 2: Sandmeyer reaction;

DOI:10.1039/c2ob00034b

Reference yield:

ethyl 3-ethoxyacrylate (1001-26-9) → 2-chloro-thiazole-4-carboxylic acid ethyl ester (41731-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide / water; 1,4-dioxane / 1 h / -10 - 20 °C

1.2: 1 h / 80 °C

1.3: 0.17 h / 20 °C

2.1: tert.-butylnitrite; copper dichloride / tetrahydrofuran; acetonitrile / 23 - 65 °C

With N-Bromosuccinimide; tert.-butylnitrite; copper dichloride; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile;

upstream raw materials:

2-aminothiazole-4-carboxylate

ethyl Bromopyruvate

ethyl 3-ethoxyacrylate

Downstream raw materials:

2-chlorothiazole-4-carboxylic acid

ethyl 2-[(1,3-benzodioxol-5-ylmethyl)(cyclohexyl)amino]-1,3-thiazole-4-carboxylate

2-chloro-1,3-thiazole-5-carboxylic acid

ethyl 2-(4-methoxyphenyl)thiazole-4-carboxylate

Refernces

• 1、 -. "HETEROCYCLIC AMINOBERBAMINE DERIVATIVES, THE PREPARATION PROCESS AND USE THEREOF". Paragraph 0106. . Retrieved 2013/07/19.
• 2、 -. "NUCLEAR TRANSPORT MODULATIORS AND USES THEREOF". Page/Page column 219-220. . Retrieved 2011/10/03.