2010-06-2

Basic information

• Product Name: 2-Amino-4-phenylthiazole
• Synonyms: 4-phenyl-1,3-thiazol-2-ylamine;2-Thiazolamine, 4-phenyl-;2-Amino-4-phenyl-1,3-thiazole;2-Thiazolamine, 4-phenyl- (9CI);WLN: T5N CSJ BZ ER;IFLAB-BB F1386-0378;ASISCHEM T31190;BUTTPARK 41\09-31
• CAS NO: 2010-06-2
• Molecular Formula: C₉H₈N₂S
• Molecular Weight: 176.24
• EINECS: 217-926-8
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiazoles;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Amines;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 2010-06-2.mol
• Article Data: 226

Chemical Properties

• Melting Point: 149-153 °C(lit.)
• Boiling Point: 363.4 °C at 760 mmHg
• Flash Point: 173.6 °C
• Appearance: White to yellow to pale orange/Crystalline Solid
• Density: 1.261g/cm³
• Vapor Pressure: 1.8E-05mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.33±0.10(Predicted)
• BRN: 128609
• CAS DataBase Reference: 2-Amino-4-phenylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-phenylthiazole(2010-06-2)
• EPA Substance Registry System: 2-Amino-4-phenylthiazole(2010-06-2)

Safety Data

• Hazard Codes: Xn,Xi,T
• Statements: 22-37/38-41-25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: XJ2878000
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 2010-06-2(Hazardous Substances Data)

Usage

Description

2-Amino-4-phenylthiazole is a synthetic intermediate with a molecular structure that features a thiazole ring fused with a phenyl group. It is characterized by the presence of an amino group at the 2nd position, which contributes to its chemical reactivity and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
2-Amino-4-phenylthiazole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as antibiotics, anti-inflammatory agents, and antiviral medications.
Used in Chemical Research:
In the field of chemical research, 2-Amino-4-phenylthiazole serves as a valuable building block for the creation of novel organic compounds. Its reactivity and structural features make it an attractive candidate for the synthesis of complex molecules with potential applications in materials science, catalysis, and other areas of chemistry.
Used in Agrochemical Industry:
2-Amino-4-phenylthiazole is also utilized in the development of agrochemicals, such as pesticides and herbicides. Its ability to form stable complexes with various metal ions and its potential to modulate biological pathways make it a promising candidate for the design of new and effective agrochemical products.

InChI:InChI=1/C9H8N2S.BrH/c10-9-11-8(6-12-9)7-4-2-1-3-5-7;/h1-6H,(H2,10,11);1H

Upstream product

• 98-86-2 acetophenone 
• 17356-08-0 thiourea 
• 5399-30-4 2-oxo-2-phenylethylthiocyanate 
• 333-20-0 potassium thioacyanate 
• 70-11-1 α-bromoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 7791-25-5 sulfuryl dichloride 
• 7719-09-7 thionyl chloride 
• 7790-94-5 chlorosulfonic acid 
• 64-17-5 ethanol 
• 131799-53-6 N-(2-Chloro-1-phenyl-1-ethylidene)isopropylamine 
• 111559-56-9 [3-(2,2-Dimethyl-propionyl)-oxiranylmethyl]-phosphonic acid diethyl ester 
• 103-85-5 monophenylthiourea 
• 111559-53-6 Diethyl (2,3-epoxy-4-oxopentyl)phosphonate 

Downstream Products

• 21392-44-9 3-phenyl-5,6-dihydro-thiazolo[3,2-a]pyrimidin-7-one 
• 533886-12-3 5-(4-nitro-phenylsulfanyl)-4-phenyl-thiazol-2-ylamine 
• 103207-52-9 5-methyl-2-phenyl-4-[(4-phenyl-thiazol-2-ylamino)-methyl]-1,2-dihydro-pyrazol-3-one 
• 59775-83-6 5-[2-(4-nitrophenyl)diazen-1-yl]-4-phenyl-1,3-thiazol-2-amine 
• 383-44-8 4-fluoro-benzenesulfonic acid-(4-phenyl-thiazol-2-ylamide) 
• 102665-83-8 N-(3-oxo-3-phenyl-propionyl)-sulfanilic acid-(4-phenyl-thiazol-2-ylamide) 
• 36234-62-5 4-phenyl-5-thiocyanato-2-aminothiazole 
• 5039-10-1 N-(4-phenyl-thiazol-2-yl)-propionamide 
• 5039-09-8 2-acetamide-4-phenyl-1,3-thiazole 
• 17649-34-2 3-phenyl-7-methyl-5H-thiazolo<3,2-a>pyrimidin-5-one 
• 87273-75-4 3‐oxo‐N‐(4‐phenylthiazol‐2yl)butanamide 
• 19959-15-0 N-[(4-nitrophenyl)methylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine 
• 107125-23-5 N-(4-phenylthiazol-2-yl)benzoylacetamide 
• 13148-56-6 N-[phenylmethylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine 

Relevant articles and documents

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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Magnetic carbon nanotube-supported imidazolium cation-based ionic liquid as a highly stable nanocatalyst for the synthesis of 2-aminothiazoles

Magnetic carbon nanotube-supported imidazolium ionic liquid (CNT-Fe3O4-IL) was synthesized and investigated using various characterization techniques, including Fourier transform infrared and Raman spectroscopies, X-ray diffraction, vibrating sample magnetometry, scanning and transmission electron microscopies, and thermogravimetric and differential thermal analyses. In order to synthesize the CNT-Fe3O4-IL nanocomposites, Fe3O4-decorated multi-walled CNTs were modified with 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride. This catalytic system was found to be a highly stable, active, reusable and solid-phase catalyst for the synthesis of 2-aminothiazoles via the one-pot reaction of ketone, thiourea and N-bromosuccinimide under mild conditions. Immobilized magnetic ionic liquid catalysis combines the advantages of ionic liquid media with magnetic solid support nanomaterials which enables the application of nanotechnology and green chemistry in chemical processes. Copyright

Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles

Asparagine functionalized aluminum oxide nanoparticles (Asp-Al2O3) have been prepared by a two-step procedure involving the grafting of Al2O3 with 3-chloropropyltrimethoxysilane (CPTMS) and subsequent organofunctionalization using asparagine amino acid. It is shown that Asp-Al2O3 exhibits as an active nanocatalyst for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine. The structure of Asp-Al2O3 was characterized by fourier transform infrared radiation (FT-TR), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this modified methodology include higher purity and excellent yield of products, greener and cleaner conditions, easy isolation of products and convenient manipulation. Moreover, immobilization of organocatalysts on the Al2O3 surface are stable under the catalytic reaction conditions resulting their efficient reuse.

A new thiazole synthesis by cyclocondensation of thioamides and alkynyl(aryl)iodonium reagents

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Novel acetamidothiazole derivatives: Synthesis and in vitro anticancer evaluation

A novel series of acetamide derivatives possessing both 2-imino-4-arylthiazoles and morpholine or different piperazines were synthesized and characterized by IR, 1H NMR, 13C NMR, elemental and mass spectral analyses. Twelve compounds were granted NSC codes at National Cancer Institute (NCI), USA for anticancer activity at a single high dose (10-5 M) in full NCI 60 cell panel. Among the compounds tested, compounds 5a and 6b were found to be the most active candidates of the synthesized series. Assessment of toxicities, druglikeness, and drug score profiles of compounds 5a and 6b are promising. Some of the synthesized compounds showed a good docking score with potential anticancer targets, chosen based on pharmacophore mapping of the established derivatives.

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Design and discovery of Novel Thiazole acetamide derivatives as anticholinesterase agent for possible role in the management of Alzheimer's

A novel series of thiazole acetamides was synthesized in excellent yields and characterized with the aid of various spectroscopic and elemental analysis. These compounds were evaluated for in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities for possible benefit in Alzheimers disease (AD). Among the synthesized compound, 6d was identified as the most potent compound of AChE (IC50= 3.14 ± 0.16 μM) with a selectivity index (SI) of 2.94 against BuChE. These compounds were further tested for inhibition of Aβ aggregation and β-secretase, where it showed potent inhibition which confirmed its multifactorial benefits in AD. The toxicity and docking study were also carried out to exemplify the pharmacological profile of compound 6d as prospective lead molecule against AD.

Discovery of potential 1,3,5-Triazine compounds against strains of Plasmodium falciparum using supervised machine learning models

The Malaria burden was an escalating global encumbrance and need to be addressed with critical care. Anti-malarial drug discovery was integrated with supervised machine learning (ML) models to identify potent thiazolyl-traizine derivatives. This assimilated approach of Direct Kernel-based Partial Least Squares regression (DKPLS) with molprint 2D fingerprints in Quantitative Structure Activity Relationship models was utilized to map the knowledge of known actives and to design novel molecules. This QSAR study had revealed the structural features required for better antimalarial activity. Two of the molecules which were designed based on the results of this QSAR study, had shown good percentage of parasitemia against both chloroquine sensitive (3D7) and chloroquine resistant (Dd2) strains of Plasmodium falciparum respectively. The IC50 of 201D and 204D was 3.02 and 2.17 μM against chloroquine resistant Dd2 strain of Plasmodium falciparum. This result had proved the efficiency of a multidisciplinary approach of medicinal chemistry and machine learning for the design of novel potent anti-malarial compounds.

Nanostarch: a novel and green catalyst for synthesis of 2-aminothiazoles

Abstract: In this work, starch nanoparticles as a green and cheap catalyst were obtained based on the precipitation of amorphous starch in ethanol. It was found that starch nanoparticles are efficient catalyst for the synthesis of 2-aminothiazoles using methylcarbonyl compounds and thiourea as precursors. The use of green and biodegradable nanostarch makes this present methodology quite simple, shorter reaction times and milder conditions, and more convenient and economically viable compared to catalyzed methods reported in the literature. Graphical abstract: [Figure not available: see fulltext.]

Nano silver particles catalyzed synthesis, molecular docking and bioactivity of α-thiazolyl aminomethylene bisphosphonates

A new series of α-thiazolyl aminomethylene bisphosphonates were synthesized by a three component reaction of 4-aryl substituted thiazol-2-amine with different dialkyl/aryl phosphites and triethyl orthoformate in the presence of Ag NPs (nano particles) as a catalyst under solvent free conditions. All the synthesized target compounds were characterized by 1H, 13C, 31P, mass and elemental analysis. The target compounds were screened for their in?vitro antioxidant, antibacterial and antifungal activity. Molecular docking studies were also performed. The results revealed that among the synthesized compounds tetramethyl(((4-(4-methoxyphenyl)thiazol-2-yl)amino) methylene)bis(phosphonate) (5d), tetramethyl(((4-(4-fluorophenyl)thiazol-2-yl)amino) methylene) bis(phosphonate) (5h), and tetramethyl(((4-(4-bromophenyl)thiazol-2-yl)amino)methylene) bis (phosphonate) (5j) showed remarkably higher antioxidant activity by DPPH and H2O2 than the standard ascorbic acid. Compounds tetramethyl(((4-phenyl thiazol-2-yl)amino) methylene) bis(phosphonate) (5a), 5d, 5h and tetraethyl(((4-(4-bromophenyl)thiazol-2-yl) amino)methylene)bis (phosphonate) (5k) showed good antibacterial activity. 5a, 5d, and 5h also showed rather higher antifungal activity than the standard flucanozole. Computational docking methods have been used to predict how several aminomethylene bisphosphonate derivatives compete against the inhibitor BPH-1330 at the crystal enzyme structure of the 4H3A protein active site and how R and R1 influence their binding ability.

Solvent-free synthesis of 2-amino-4-arylthiazoles under microwave irradiation

2-Amino-4-arylthiazoles were prepared in a one-pot solvent-free procedure by reaction of p-substituted acetophenones with thiourea and iodine under microwave irradiation.

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

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.