2591-14-2

Basic information

• Product Name: 1,3-BENZOTHIAZOL-2-YL 3-CHLOROPROPYL SULFIDE
• Synonyms: 1,3-BENZOTHIAZOL-2-YL 3-CHLOROPROPYL SULFIDE;2-(3-CHLORO-PROPYLSULFANYL)-BENZOTHIAZOLE;2-[(3-Chloropropyl)sulfanyl]-1,3-benzothiazole
• CAS NO: 2591-14-2
• Molecular Formula: C₁₀H₁₀ClNS₂
• Molecular Weight: 243.78
• Mol File: 2591-14-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-BENZOTHIAZOL-2-YL 3-CHLOROPROPYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZOTHIAZOL-2-YL 3-CHLOROPROPYL SULFIDE(2591-14-2)
• EPA Substance Registry System: 1,3-BENZOTHIAZOL-2-YL 3-CHLOROPROPYL SULFIDE(2591-14-2)

Safety Data

• Hazardous Substances Data: 2591-14-2(Hazardous Substances Data)

Usage

Chemical class

Benzothiazole derivatives

Structure

Consists of a benzothiazole group attached to a 3-chloropropyl group through a sulfur atom

Applications

a. Organic synthesis
b. Material science
c. Pharmaceutical research and development

Building block

Used for the synthesis of various organic compounds and materials with specific properties

Biological activities

Presence of the benzothiazole moiety, which is known for its biological activities and pharmacological properties

Safety precautions

Handle with caution and follow proper safety procedures due to potential health and environmental hazards

Upstream product

• 142-28-9 1,3-Dichloropropane 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 109-70-6 1.3-chlorobromopropane 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 1165930-90-4 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine 
• 1165930-93-7 6-[3-(benzothiazol-2-ylthio)propoxy]-N-(4-bromo-2-ethylphenyl)-7-methoxyquinazolin-4-amine 
• 1165930-96-0 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-(4-methoxyphenyl)quinazoline-4-amine 
• 1165930-99-3 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-(4-methylphenyl)quinazolin-4-amine 
• 1165930-87-9 6-[3-(benzothiazol-2-ylthio)propoxy]-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 1427471-21-3 2-{[3-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-22-4 2-{[3-(3,5-bis(3,5-dinitrophenyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-23-5 2-{[3-(3,5-bis(3,5-dinitrophenyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-24-6 2-({3-[3,5-bis(2,4-dichlorophenyl)-1H-1,2,4-triazol-1-yl]propyl}sulfanyl)-1,3-benzothiazole 
• 1427471-25-7 2-{[3-(3,5-di(phenoxymethyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-28-0 2-({3-[3,5-bis(4-chlorophenoxymethyl)-1H-1,2,4-triazol-1-yl]propyl}sulfanyl)-1,3-benzothiazole 

Relevant articles and documents

Novel imidazole derivatives as heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity in human-derived cancer cell lines

Heme oxygenase (HO) is a cytoprotective enzyme that can be overexpressed in some pathological conditions, including certain cancers. In this work, novel imidazole derivatives were designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme

One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride

The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.

Synthesis and biological evaluation of some novel 3,5-disubstituted-1,2,4- triazole incorporated 2-mercaptobenzothiazoles

Several 2-mercaptobenzothiazole derivatives 5a-i containing 1,2,4-triazole moiety incorporating two additional substituents were synthesized. All the newly synthesized compounds were tested for in vitro activity against certain strains of bacteria such as Enterococcus faecalis, Bacillus coagulans, Pseudomonas aeruginosa, Escherichia coli and Candida albicans. Compound 5a showed significant activity against the Gram-negative bacteria Escherichia coli. Compounds 5a-i were also screened for their antifungal activity against Candida albicans and compounds 5a, 5b, 5d and 5g displayed significant activity against this fungus. Some of these compounds were evaluated for their in vivo anti-inflammatory activity, acute toxicity and ulcerogenic actions. Tested compounds 5g and 5h showed significant anti-inflammatory activity and significant gastrointestinal protection compared to the standard drug diclofenac sodium. Molecular modeling studies of the synthesized compounds are presented.