2103-94-8

Basic information

• Product Name: 2-Amino-4-(4-bromophenyl)thiazole
• Synonyms: OTAVA-BB BB0125210401;TIMTEC-BB SBB000941;AURORA 5312;BUTTPARK 41\03-36;4-(4-BROMOPHENYL)-1,3-THIAZOLE-2-YLAMINE;4-(4-BROMO-PHENYL)-THIAZOL-2-YLAMINE;4-(4-BROMOPHENYL)THIAZOL-2-AMINE;4-(4-BROMOPHENYL)-1,3-THIAZOL-2-AMINE
• CAS NO: 2103-94-8
• Molecular Formula: C₉H₇BrN₂S
• Molecular Weight: 255.13
• Product Categories: Sulphur Derivatives;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks
• Mol File: 2103-94-8.mol
• Article Data: 98

Chemical Properties

• Melting Point: 183-187 °C(lit.)
• Boiling Point: 410.943 °C at 760 mmHg
• Flash Point: 202.331 °C
• Appearance: beige to yellow powder
• Density: 1.637 g/cm³
• Vapor Pressure: 5.8E-07mmHg at 25°C
• Refractive Index: 1.684
• PKA: 3.95±0.10(Predicted)
• Water Solubility: Insoluble
• BRN: 153896
• CAS DataBase Reference: 2-Amino-4-(4-bromophenyl)thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-(4-bromophenyl)thiazole(2103-94-8)
• EPA Substance Registry System: 2-Amino-4-(4-bromophenyl)thiazole(2103-94-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2103-94-8(Hazardous Substances Data)

Usage

Chemical Properties

beige to yellow powder

InChI:InChI=1/C9H7BrN2S/c10-7-3-1-6(2-4-7)8-5-13-9(11)12-8/h1-5H,(H2,11,12)

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Relevant articles and documents

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2-Aminothiazole is a valuable synthon in organic synthesis and an important structural unit of pharmaceutically active drugs. It is accessible via several synthetic routes. In the current account, compound 4 {4-(4-bromophenyl) thiazol-2-amine} was synthesized by employing a recently reported procedure of Gabriel synthesis using Lawesson reagent. The title compound was characterized through spectro-elemental analytical data, and its crystal structure was determined by single-crystal X-ray diffraction. The torsion angles, bond lengths, and bond strengths between the planes of the thiazole and phenyl rings were optimized by theoretical calculations by applying the B3LYP/6-311++G(d,p) level for the purpose of investigating the conformational effects on the stabilization of the crystal packing. HOMO-LUMO analysis, vibrational analysis, and thermodynamic parameters were also investigated. A detailed analysis of the intermolecular interactions of thiazole moiety bearing the amino and bromophenyl ring has been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. The relative contributions of the main intermolecular contacts as well as the enrichment ratios derived from the Hirshfeld surface analysis establish the 2-aminothiazole synthon to be a molecule of great interest. DNA binding studies pointed towards anticancer potency of the synthesized compound via reversible binding.

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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.