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

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

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

• 64-17-5 ethanol 
• 3282-32-4 2-diazo-acetophenone 
• 17356-08-0 thiourea 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 538-28-3 S-benzylisothiourea hydrochloride 
• 56-04-2 6-methyl-2-thiouracil 
• 95337-93-2 4-phenyl-2-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole 
• 111559-53-6 Diethyl (2,3-epoxy-4-oxopentyl)phosphonate 
• 598-52-7 1-(methyl)-thiourea 
• 111559-55-8 (3-Isobutyryl-oxiranylmethyl)-phosphonic acid diethyl ester 
• 532-27-4 1-chloroacetophenone 
• 4651-78-9 2-bromo-1-phenylethylidenemalononitrile 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 

Downstream Products

• 113408-24-5 N-(4-phenyl-thiazol-2-yl)-succinimide 
• 14397-15-0 nicotinic acid-(4-phenyl-thiazol-2-ylamide) 
• 14397-16-1 N-2-isonicotinoyl-4-phenyl-thiazol-2-amine 
• 103155-05-1 7-[(4-phenyl-thiazol-2-ylamino)-methyl]-quinolin-8-ol 
• 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 

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.

Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe3O4 nanoparticle-: N -halo reagent catalytic system

An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems. 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) as N-halo reagents were explored and the best results were obtained for DCDMH. Fe3O4 nanoparticle-DCDMH as an active, reusable, excellent, highly stable magnetic catalyst was used in this process. Advantages of this efficient method include greener and cleaner conditions, shorter reaction time, excellent yield of products, easy separation using a simple external magnetic field, low cost and operational simplicity.

Joining Microfluidics with Infrared Photodissociation: Online Monitoring of Isomeric Flow-Reaction Intermediates

A cryogenic ion trap vibrational spectrometer is combined with a microfluidic chip reactor in a proof-of-principle experiment on the Hantzsch cyclization reaction forming 2-amino-4-phenyl thiazole from phenacyl bromide and thiourea. First, the composition of the reaction solution is characterized using electrospray-ionization mass spectrometry combined with two-color infrared photodissociation (IRPD) spectroscopy. The latter yields isomer-specific vibrational spectra of the reaction intermediates and products. A comparison to results from electronic structure calculations then allows for an unambiguous structural assignment and molecular-level insights into the reaction mechanism. Subsequently, we demonstrate that isomeric and isobaric ions can be selectively monitored online with low process time, i.e., using a single IRPD wavelength per isomer, as the chip reaction parameters are varied.

MNPs@SiO2-Pr-AP: A new catalyst for the synthesis of 2-amino-4-aryl thiazole derivatives

A simple and efficient synthesis of 2-amino-4-aryl thiazole derivatives was carried out through the reaction of substituted acetophenones and thiourea using three different types of catalytic systems including N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and a combination of TBBDA and nano-magnetic catalyst supported with functionalized 4-amino-pyridine silica (MNPs@SiO2-Pr-AP). The results showed that the use of TBBDA along with the MNPs@SiO2-Pr-AP gains the highest yields of the products in the shortest reaction time.

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

Copper acetate-catalyzed, mild, highly efficient, and practical synthesis of thiazoles and aminothiazoles

A mild and highly efficient synthesis of thiazoles by the condensation of α-bromo ketones with thiourea in the presence of a catalytic amount of copper acetate at room temperature has been described. The method is applicable for a variety of aryl and alkyl α-bromo ketones. The catalyst is inexpensive, and substituted thiazoles are obtained in good yields.

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.

Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80?°C in DMSO medium. A plausible mechanism is proposed in which α-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.

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.

Synthesis of 2-amino-4-phenylthiazole under conditions of microwave irradiation

The possibility of preparing 2-amino-4-phenylthiazole from acetophenone, iodine, and thiourea under the conditions of microwave irradiation was studied.