78485-37-7

Basic information

• Product Name: Ethyl 2-chloro-6-benzothiazolecarboxylate
• Synonyms: Ethyl2-chlorobenzo[d]thiazole-6-carboxylate;2-Chlorobenzothiazole-6-carboxylic acid ethyl ester;Ethyl 2-chloro-6-benzothiazolecarboxylate
• CAS NO: 78485-37-7
• Molecular Formula: C₁₀H₈ClNO₂S
• Molecular Weight: 241.69
• Mol File: 78485-37-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 90-92°
• Boiling Point: 340.5 °C at 760 mmHg
• Flash Point: 159.7 °C
• Appearance: /
• Density: 1.400
• Vapor Pressure: 8.58E-05mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.37±0.10(Predicted)
• CAS DataBase Reference: Ethyl 2-chloro-6-benzothiazolecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-chloro-6-benzothiazolecarboxylate(78485-37-7)
• EPA Substance Registry System: Ethyl 2-chloro-6-benzothiazolecarboxylate(78485-37-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 78485-37-7(Hazardous Substances Data)

Usage

Description

Ethyl 2-chloro-6-benzothiazolecarboxylate, also known as Ethyl 2-chloro-6-(phenylthio)benzothiazole-7-carboxylate, is a chemical compound with the molecular formula C13H9ClNOS. It is a versatile building block in the synthesis of pharmaceuticals and agrochemicals, known for its potential as an anti-cancer agent, and also possesses anti-inflammatory and anti-fungal properties.

Uses

Used in Pharmaceutical Industry:
Ethyl 2-chloro-6-benzothiazolecarboxylate is used as a building block for the synthesis of various pharmaceuticals due to its versatile chemical properties and potential therapeutic applications.
Used in Agrochemical Industry:
Ethyl 2-chloro-6-benzothiazolecarboxylate is also utilized as a building block in the development of agrochemicals, contributing to its role in pest control and crop protection.
Used in Anti-cancer Applications:
Ethyl 2-chloro-6-benzothiazolecarboxylate is used as a potential anti-cancer agent for its ability to inhibit the growth of cancer cells, offering a promising avenue for cancer treatment research.
Used in Anti-inflammatory and Anti-fungal Applications:
Due to its anti-inflammatory and anti-fungal properties, Ethyl 2-chloro-6-benzothiazolecarboxylate is used in the development of treatments for inflammatory conditions and fungal infections.
It is important to handle Ethyl 2-chloro-6-benzothiazolecarboxylate with care, as it is classified as a hazardous substance and can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C10H8ClNO2S/c1-2-14-9(13)6-3-4-7-8(5-6)15-10(11)12-7/h3-5H,2H2,1H3

Upstream product

• 50850-93-6 ethyl 2-aminobenzothiazole-6-carboxylate 
• 73792-12-8 ethyl 4-amino-3-fluorobenzoate 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 1383739-76-1 C₃₀H₃₀F₃N₃O₅S 
• 1383739-48-7 ethyl 2-(4-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylate 
• 1383739-59-0 C₂₉H₂₈F₃N₃O₄S 
• 1383739-81-8 2-(4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid 
• 1383739-80-7 ethyl 2-(4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylate 

Relevant articles and documents

Benzothiazole derivatives and medical application thereof

The invention discloses benzothiazole derivatives and a medical application thereof. The invention provides a series of benzothiazole derivatives, and research finds that the series of benzothiazole derivatives can effectively improve the expression level

FXR RECEPTOR MODULATOR, PREPARATION METHOD THEREFOR, AND USES THEREOF

The present disclosure disclosed a modulator of FXR receptor and preparation and use thereof, which relates to the technical filed of medicinal chemistry. The present disclosure provides a modulator of FXR receptor having a structural formula I or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, which can combine with FXR receptor (that is NR1H4) and be acted as a FXR agonist or a partial agonist for preventing and treating the disease mediated by FXR, such as chronic intrahepatic or extrahepatic cholestasis, hepatic fibrosis caused by chronic cholestasis or acute intrahepatic cholestasis, chronic hepatitis B, gallstone, hepatic carcinoma, colon cancer or intestinal inflammatory disease, etc. Specifically, for some chemical compounds, their EC50 for FXR agonist activity reach below 100nM, which show an excellent FXR agonist activity and an excellent prospect to provide a new pharmaceutical selection in clinical treatment for the disease mediated by FXR.

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles

Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.