2103-99-3

Basic information

• Product Name: 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE
• Synonyms: 2-AMINO 4(P-CHLORO)PHENYL THIAZOLE;2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE;AKOS B000490;AKOS BBS-00000674;4-(4-CHLORO-PHENYL)-THIAZOL-2-YLAMINE;4-(4-CHLOROPHENYL)-1,3-THIAZOL-2-AMINE;AURORA 13234;BUTTPARK 18\03-88
• CAS NO: 2103-99-3
• Molecular Formula: C₉H₇ClN₂S
• Molecular Weight: 210.68
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks;Building Blocks;C8 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 2103-99-3.mol

Chemical Properties

• Melting Point: 169-171 °C(lit.)
• Boiling Point: 389.8 °C at 760 mmHg
• Flash Point: 189.6 °C
• Appearance: White to off-white/Powder
• Density: 1.389 g/cm³
• Vapor Pressure: 2.77E-06mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.95±0.10(Predicted)
• BRN: 153889
• CAS DataBase Reference: 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE(2103-99-3)
• EPA Substance Registry System: 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE(2103-99-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: XJ1026732
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 2103-99-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a building block in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE serves as a key intermediate in the preparation of more complex molecules. For instance, it was used in the preparation of 2-chloroacetamido-4-(4-chlorophenyl)thiazole, which may have specific applications in various industries.

InChI:InChI=1/C9H7ClN2S/c10-7-3-1-6(2-4-7)8-5-13-9(11)12-8/h1-5H,(H2,11,12)

Upstream product

• 99-91-2 para-chloroacetophenone 
• 17356-08-0 thiourea 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 114710-74-6 3-Allyl-2-[(Z)-4-(4-chloro-phenyl)-thiazol-2-ylimino]-thiazolidin-4-one 
• 937-20-2 p-chlorophenacyl chloride 
• 333-20-0 potassium thioacyanate 
• 25917-49-1 1-(4-chlorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 104-88-1 4-chlorobenzaldehyde 
• 114710-70-2 N¹-<4-(p-chlorophenyl)-2-thiazolyl>-N²-allylthiourea 
• 53896-48-3 2-iodo-4'-chloroacetophenone 
• 1073-67-2 4-vinylbenzyl chloride 
• 19339-59-4 1-(4-chloro-phenyl)-2-thiocyanato-ethanone 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 325-00-8 4-fluoro-benzenesulfonic acid-[4-(4-chloro-phenyl)-thiazol-2-ylamide] 
• 102884-74-2 4,4'-bis-(4-chloro-phenyl)-5,5'-benzylidene-bis-thiazol-2-ylamine 
• 77925-45-2 N-acetyl-sulfanilic acid-[4-(4-chloro-phenyl)-thiazol-2-ylamide] 
• 56921-67-6 3-(4-chloro-phenyl)-6-thiophen-2-yl-imidazo[2,1-b]thiazole 
• 39564-98-2 3-(4-chloro-phenyl)-pyrido[2,3-d]thiazolo[3,2-a]pyrimidin-5-one 
• 74636-82-1 3-[4-(4-chloro-phenyl)-thiazol-2-yl]-2-methyl-3H-quinazolin-4-one 
• 53183-54-3 N-{[4-(4-chloro-phenyl)-thiazol-2-ylamino]-methyl}-phthalimide 
• 74636-88-7 3-[4-(4-chloro-phenyl)-thiazol-2-yl]-2-phenyl-3H-quinazolin-4-one 
• 15948-94-4 3-(4-chloro-phenyl)-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 22757-83-1 4-acetylamino-naphthalene-1-sulfonic acid 4-(4-chloro-phenyl)-thiazol-2-ylamide 
• 23893-46-1 6-acetylamino-naphthalene-2-sulfonic acid 4-(4-chloro-phenyl)-thiazol-2-ylamide 
• 74675-85-7 N-[4-(4-chloro-phenyl)-thiazol-2-yl]-2-hydroxy-5-nitro-benzamide 
• 50728-81-9 3,5-dichloro-N-[4-(4-chloro-phenyl)-thiazol-2-yl]-2-hydroxy-benzamide 
• 74675-80-2 3,5-dibromo-N-[4-(4-chloro-phenyl)-thiazol-2-yl]-2-hydroxy-benzamide 

Relevant articles and documents

1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles

In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]

Solid state thiazole-based fluorophores: Promising materials for white organic light emitting devices

A facile and more efficient solvent-free mechanochemical synthetic route has been developed for the synthesis of a series of solid state white light emissive thiazole-based donor-acceptor (D-A) type fluorophores, 2-(3-pyridyl)/2-aminothiazoles from ω-bromomethylketones and pyridine-3-carbothioamide/thiourea in the presence of silica-supported HClO4 as a reusable solid Br?nsted acid catalyst at RT. The photophysical and electrochemical properties of these compounds have been derived. Most of the studied D-A type solid thiazole-based fluorophores emitted white light and it can be tuned from warm - ideal - cold white light by introduction of a variety of substituents at 4th position of 2-(3-pyridyl)/2-aminothiazoles. Further, HOMO and LUMO energy levels of the titled compounds are found to be in the range ?5.52 eV to ?5.72 eV and ?1.84 eV to ?2.45 eV, respectively. The lifetimes of these levels of thiazole-based fluorophores have been determined through luminescence decay curves and are found to be in the range of 7.7–11 μs. The photophysical and electrochemical properties of the synthesized thiazole-based fluorophores indicate that the compounds could be promising materials for white organic light emitting devices.

Molecular properties prediction, synthesis, and antimicrobial activity of bis(azolyl)sulfonamidoacetamides

A library of bis(azolyl)sulfonamidoacetamides was prepared by the reaction of azolylsulfonylamines with azolylchloroacetamides in the presence of pyridine/4-(dimethylamino)pyridine (DMAP) under ultrasonication. The reaction proceeded well with DMAP, resulting in a higher yield of the products. The antimicrobial activity of the compounds indicated that N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl)amino}-2-oxoethyl)sulfamoyl]-4-phenylthiazol-2-yl}benzamide (22a), N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chlorophenyl)thiazol-2-yl}benzamide (22c), and N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chloro-phenyl)-1H-imidazol-2-yl}benzamide (24c) exhibited a low minimal inhibitory concentration (MIC) against Bacillus subtilis, equal to the standard drug, chloramphenicol. Compounds 22c and 24c also showed low MICs against Aspergillus niger, equal to the standard drug, ketoconazole. The molecular properties of the synthesized molecules were studied to identify druglikeness properties of the target compounds. On the basis of molecular properties prediction, 19a, 19b, 20b, 20c, 21a–c, 22b, 22c, and 23a–c can be treated as drug candidates.

INHIBITOR COMPOUNDS

The disclosure relates to heterocyclic compounds and methods for their preparation. The disclosure provides compounds that may have beneficial therapeutic activity in the treatment of a disease or condition mediated by excessive or otherwise undesirable Des1 and/or fibrotic activity.

Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 ± 0.16 μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 ± 2.4, 51.09 ± 2.6 and 51.41 ± 2.3 nM, respectively. The cell cycle analysis of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. In apoptosis assay, the same two compounds were able to induce significant levels of early and late apoptosis. In a similar manner to Sorafenib, docking of target compounds with VEGFR-2 protein 4ASD showed HB with Cys919 in hinge region of enzyme and HB with both Glu885 and Asp1046 in gate area. Using SwissADME, all target compounds were predicted to be highly absorbed from gastrointestinal tract with no BBB permeability. It is clear that the two compounds are promising antiproliferative candidates that require further optimization.

Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds 7c, 7d and 7e exhibited significant antiproliferative activities at 10?5 M dose. Compound 7c exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, compound 7d showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. Compound 7c inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival. The flow cytometric analysis showed that 7c displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. Compound 7c clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-positive and Gram-negative as well as Candida albicans. Only compound 7d exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound.

Synthesis of 6-membered-ring fused thiazine-dicarboxylates and thiazole-pyrimidines via one-pot three-component reactions

A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

Synthesis of new thiazole derivatives and evaluation of their antimicrobial and cytotoxic activities

Novel 2-heteroaryl-N-[4-(substituted aryl)thiazol-2-yl]propanamide derivatives (7a–7o) were synthesized and investigated for their antimicrobial activity. Among the tested compounds, 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propan

Biological evaluation and synthesis of thiazole schiff base derivatives

In this study, we report the synthesis of thiazole Schiff base derivatives (Z1-Z16) and their tyrosinase inhibitory activity, anti-oxidant activities. Mushroom tyrosinase inhibitory assay showed compound Z8 (IC50 = 2.78 ± 0.08 μM) inhibited tyrosinase more than kojic acid (49.39 ± 0.17 μM), and docking study indicated compound Z8 (-7.32 kcal/mol) had stronger binding affinities for tyrosinase than kojic acid (-5.7 kcal/mol). Phenolic hydroxyl group on 4-position (R2) of compound Z8 can form Metal - Acceptor with Cu401. The results of inhibition kinetics studies demonstrated that compound Z8 was mixed type inhibitor. The anti-browning effects manifested compound Z8 expressed satisfactory effects in anti-browning of fresh-cut apples and fresh-cut potato. All the results indicated that thiazole Schiff base derivatives might be promising leading compounds as tyrosinase inhibitors and anti-oxidant agents.

Aiding the versatility of simple ammonium ionic liquids by the synthesis of bioactive 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives

Simple ammonium ionic liquids [ILs] are efficient, green, environmentally friendly catalysts in promoting the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction to afford 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives respectively by eliminating the need for harmful volatile organic solvents. These [ILs] are air and water stable, easy to prepare and cost-effective. The effects of the anions and cations present in [IL] on reactions were investigated. The results clearly indicated that the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction were heavily influenced by the acidity of [IL], and among various ammonium ionic liquids, [Et3NH][HSO4] showed the best catalytic activity. Furthermore, [IL] could be easily separated and reused with a slight loss of its activity. This technique provided a good alternative way for the industrial synthesis of 1,2,3,4-tetrahydropyrimidinones, 2-aminothiazoles and quinazolinones. The present processes are eco-friendly methods for the synthesis of these derivatives authenticated by several green parameters, namely,E-factor, process mass intensity, reaction mass efficiency, atom economy, and carbon efficiency.