154715-81-8

Basic information

• Product Name: 2-(3,5-DIMETHYL-PHENYL)-BENZOOXAZOLE
• Synonyms: 2-(3,5-DIMETHYL-PHENYL)-BENZOOXAZOLE
• CAS NO: 154715-81-8
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.274
• Mol File: 154715-81-8.mol

Chemical Properties

• Melting Point: 121-122 °C
• Boiling Point: 342.6±31.0 °C(Predicted)
• Appearance: /
• Density: 1.131±0.06 g/cm3(Predicted)
• PKA: 1.16±0.10(Predicted)
• CAS DataBase Reference: 2-(3,5-DIMETHYL-PHENYL)-BENZOOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-DIMETHYL-PHENYL)-BENZOOXAZOLE(154715-81-8)
• EPA Substance Registry System: 2-(3,5-DIMETHYL-PHENYL)-BENZOOXAZOLE(154715-81-8)

Safety Data

• Hazardous Substances Data: 154715-81-8(Hazardous Substances Data)

Usage

Usage

Fluorescent dye in biology and histology, medical diagnostics, and textile industry for dyeing fabrics

Chemical Structure

Benzene ring fused with an oxazole ring, 3,5-dimethylphenyl group

Physical Appearance

Blue dye

Properties

Emits fluorescence when exposed to ultraviolet light

Role

Visualization of cellular structures under a microscope, staining microscopic specimens for imaging and analysis.

Upstream product

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• 2905-27-3 3,5-dimethyl-benzenesulfonyl chloride 
• 1070731-22-4 3,5-dimethylphenyl methanesulfonate 
• 95127-25-6 3,5-dimethylphenyl 4-methylbenzenesulfonate 
• 22445-41-6 3,5-dimethylphenyl iodide 

Relevant articles and documents

(N-heterocyclic carbene)PdCl(N-heterocyclic carboxylate) complexes: Synthesis and catalytic activities towards arylation of benzoxazoles with aryl halides

A series of N-heterocyclic carboxylate-stabilized N-heterocyclic carbene palladium complexes have been synthesized and fully characterized. The solid-state structures indicate that each of the palladium centers is coordinated by an N-heterocyclic carbene, a chloride and a bidentate N,O-donor N-heterocyclic carboxylate ligand. The catalytic performance of the complexes was screened and the results revealed that the complexes exhibit moderate to high catalytic activities for the direct C─H bond arylation of benzoxazoles with aryl bromides.

Visible Light-Induced Copper-Catalyzed C—H Arylation of Benzoxazoles?

A general method for visible light-induced copper-catalyzed arylation of sp2 C—H bonds of azoles has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide as base. A variety of azoles including benzooxazole and benzothiazole can be arylated. Furthermore, electron-poor heterocycles such as thiophene possessing one electron-withdrawing group can also be arylated.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Ni-Catalyzed C?F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles

A Ni-catalyzed C?F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system.

Unsymmetrical Pincer N -Heterocyclic Carbene-Nitrogen-Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp2-H Arylation of Benzoxazoles

An unsymmetrical pincer N-heterocyclic carbene-nitrogen-phosphine (CNP) and its palladium complexes PdCl2(κ2-CP) (4) and [PdCl(κ3-CNP)]PF6 (5·PF6) were synthesized. NMR spectra disclosed that the transformation of complex 4 structure occurred in the solution. Further NMR experimental and single crystal structure analysis of complex 4 provided unequivocal and structural evidence for the formation of complex [PdCl(κ3-CNP)]Cl (5·Cl) in the solution of complex 4. The catalytic performance of palladium complexes 4 and 5·PF6 was investigated with the direct Csp2-H arylation of benzoxazoles with aryl bromides. Notably, aryl bromides could give up to 97% arylation products in the presence of 0.5% complex 4. For ortho-substituted substrates, the steric hindrance had a significant impact, but product yields could be improved remarkably by extending reaction time. This result implied the catalytic active species in this system was stable and kept in a long lifetime. The flexible backbone and unsymmetrical pincer structure with a flank N-heterocyclic carbine should be a feasible strategy to realize an efficient catalytic transformation. This simple catalyst system first realized the direct arylation of aryl bromides with a catalyst loading as low as 0.25% without excessive base and copper as assistant catalyst.

An iron and copper system catalyzed C-H arylation of azoles with arylboronic acids

An efficient, environmentally friendly, and economical new method for arylation reactions of azoles with arylboronic acids via copper-iron-catalyzed C-H and C-B bond activation has been developed. The protocol tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, and trifluoromethyl groups.

Chelating palladium complexes containing pyridine/pyrimidine hydroxyalkyl di-functionalized N-heterocyclic carbenes: Synthesis, structure, and catalytic activity towards C-H activation

The synthesis of novel chelating palladium complexes containing pyridine/pyrimidine hydroxyalkyl di-functionalized N-heterocyclic carbenes (NHCs) via direct metallation of the precursor imidazolium salts is presented. The structure has been characterized unambiguously by X-ray single crystal analysis. Catalytic activity investigation showed that the complexes catalyse the direct C-H bond arylation of (benzo)oxazoles efficiently when using tBuOLi as base and DMF as solvent.

Trichloroisocyanuric Acid/Triphenylphosphine-Mediated Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles

A new and efficient method for preparation of benzimidazoles, benzoxazoles, and benzothiazoles from reactions of different carboxylic acids with o-phenylenediamine, o-aminophenol, and o-aminothiophenol in the presence of triphenylphosphine/trichloroisocyanuric acid system is presented. The desired products have been characterised on the basis of spectral (infrared, NMR, mass spectrometry) data, and the mechanism of their formation is proposed. The remarkable advantages are the inexpensive and readily available reagent, simple procedure, mild conditions, and good-to-excellent yields.

Copper-catalyzed selective arylations of benzoxazoles with aryl iodides

A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.

Palladium-catalyzed desulfitative arylation of azoles with arylsulfonyl hydrazides

Palladium-catalyzed desulfitative and denitrogenative arylation of azoles with arylsulfonyl hydrazides has been achieved. A broad scope of azoles and arylsulfonyl hydrazides has been used to produce arylated azoles in high yields.