93209-97-3

Basic information

• Product Name: 2-Thiazolamine,4-(2,4-dichlorophenyl)-
• Synonyms: 2-Amino-4-(2,4-dichlorophenyl)thiazole;4-(2,4-Dichlorophenyl)thiazol-2-amine; [4-(2,4-Dichlorophenyl)thiazol-2-yl]amine
• CAS NO: 93209-97-3
• Molecular Formula: C₉H₆Cl₂N₂S
• Molecular Weight: 245.1283
• Mol File: 93209-97-3.mol

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 396°Cat760mmHg
• Flash Point: 193.3°C
• Appearance: /
• Density: 1.498g/cm³
• Vapor Pressure: 1.76E-06mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(93209-97-3)
• EPA Substance Registry System: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(93209-97-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 93209-97-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiazolamine,4-(2,4-dichlorophenyl)is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of bioactive molecules with potential therapeutic applications.
Used in Medicinal Chemistry Research:
Amiphenazole is utilized as a research compound in medicinal chemistry, where it aids in the exploration and understanding of its antiproliferative and antifungal properties, as well as its potential as a drug candidate for treating cancer and infectious diseases.
Used in Cancer Treatment:
2-Thiazolamine,4-(2,4-dichlorophenyl)is employed as a potential drug candidate in oncology, leveraging its antiproliferative properties to inhibit the growth and progression of cancer cells.
Used in Infectious Disease Treatment:
Amiphenazole is used as a potential therapeutic agent in the treatment of infectious diseases, capitalizing on its antifungal properties to combat fungal infections.
Used in Antihistamine Medication Development:
2-Thiazolamine,4-(2,4-dichlorophenyl)is utilized in the development of antihistamine medications due to its activity as a histamine H1 receptor antagonist, which can help alleviate symptoms associated with allergic reactions.

InChI:InChI=1/C9H6Cl2N2S/c10-5-1-2-6(7(11)3-5)8-4-14-9(12)13-8/h1-4H,(H2,12,13)

Upstream product

• 17356-08-0 thiourea 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 68716-47-2 2,4-dichlorophenylboronic acid 

Downstream Products

• 4864-67-9 C-chloro-N-[4-(2,4-dichloro-phenyl)-thiazol-2-yl]-methanesulfonamide 
• 117134-43-7 N-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-S-trichloromethyl-thiohydroxylamine 
• 125298-83-1 C₁₂H₁₀Cl₂N₂S₃ 
• 153776-98-8 [4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-dithiocarbamic acid methyl ester 
• 335387-29-6 2-chloro-N-[4-(2,4-dichloro-phenyl)-thiazol-2-yl]-acetamide 
• 477568-91-5 N-[4-(2,4-dichloro-phenyl)-thiazol-2-yl]-2,6-difluoro-benzamide 
• 1312809-91-8 4-(4-(2,4-dichlorophenyl)thiazol-2-yl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one 
• 1398574-79-2 C₁₄H₁₂Cl₂N₂O₃S 
• 544463-71-0 4-((4-(2,4-dichlorophenyl)thiazol-2-yl)amino)-4-oxobutanoic acid 

Relevant articles and documents

Solvent-free sonochemical kabachnic-fields reaction to synthesize some new α-aminophosphonates catalyzed by nano-BF3?SiO2

To obtain a rapid, efficient synthesis of some new α-aminophosphonates, ultrasonic irradiation has been applied to the reaction mixtures containing amine, aromatic or heteroaromatic aldehydes and triethyl phosphite. The Kabachnik-Fields reaction was performed by using nano-BF3?SiO2 as a recyclable catalyst under solvent free conditions. Key advantages of this procedure consist in the eco-friendly and highly efficient reaction conditions, high yields, an easy work-up procedure, short reaction times and solvent free conditions. All title compounds were characterized by spectral and elemental analysis. They were further screened for their in vitro antioxidant activity by the DPPH, O2? and NO methods. The majority of the title compounds showed good antioxidant activity when compared with the standard antioxidants.

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Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

Our group has previously reported several indolecarboxamides exhibiting potent antitubercular activity. Herein, we rationally designed several arylcarboxamides based on our previously reported homology model and the recently published crystal structure of the mycobacterial membrane protein large 3 (MmpL3). Many analogues showed considerable anti-TB activity against drug-sensitive (DS) Mycobacterium tuberculosis (M. tb) strain. Naphthamide derivatives 13c and 13d were the most active compounds in our study (MIC: 6.55, 7.11 μM, respectively), showing comparable potency to the first line anti-tuberculosis (anti-TB) drug ethambutol (MIC: 4.89 μM). In addition to the naphthamide derivatives, we also identified the quinolone-2-carboxamides and 4-arylthiazole-2-carboxamides as potential MmpL3 inhibitors in which compounds 8i and 18b had MIC values of 9.97 and 9.82 μM, respectively. All four compounds retained their high activity against multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tb strains. It is worth noting that the two most active compounds 13c and 13d also exhibited the highest selective activity towards DS, MDR and XDR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 227 μM], indicating their potential lack of cytotoxicity. The four compounds were docked into the MmpL3 active site and were studied for their drug-likeness using Lipinski's rule of five.

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SUBSTITUTED PROPANAMIDES AS INHIBITORS OF NUCLEASES

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Microwave-assisted synthesis of novel N-(4-phenylthiazol-2-yl)-benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides inspired by marine topsentines and nortopsentines

We report the synthesis of novel N-(4-phenylthiazol-2-yl)-substituted benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides, which were inspired by marine topsentines and nortopsentines. Condensation of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) with various ortho-halogenated anilines, aminopyridines and aminophenols gave the corresponding aryliminodithiazoles in good to excellent yields. Copper(I)-mediated or nucleophilic-assisted cyclization of aryliminodithiazoles furnished cyano-functionalized benzo[d]thiazoles, thiazolo[4,5-b]- and thiazolo[5,4-b]-pyridines and benzo[d]oxazoles. The latter were condensed with substituted 4-phenylthiazol-2-amines to furnish twenty seven new polyaromatic carboximidamides in moderate to good yields.

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