189120-01-2

Usage

Molecular Weight

214.06 g/mol

Class

Heterocyclic compound

Structure

Five-membered aromatic ring containing one oxygen and one nitrogen atom, with a 4-bromophenyl group attached to the second carbon atom.

Bromine Content

The presence of a bromine atom in the phenyl group.

Potential Applications

Pharmaceutical, agrochemical, and materials science industries.

Safety Precautions

Handle with caution and follow proper safety protocols in a laboratory setting.

Upstream product

• 141-43-5 ethanolamine 
• 1122-91-4 4-bromo-benzaldehyde 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 1943-83-5 2-chloroethyl isothiocyanate 
• 586-76-5 4-Bromobenzoic acid 
• 26197-93-3 p-bromothiobanzamide 
• 586-75-4 4-chlorobenzoyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 57728-67-3 N-(2-hydroxyethyl)-p-bromobenzamide 
• 873-75-6 4-bromobenzenemethanol 
• 18292-63-2 1-(p-bromobenzoyl)aziridine 

Downstream Products

• 914076-87-2 C₁₈H₁₅NO 
• 1142955-23-4 C₂₀H₁₆N₂O₂ 
• 1142955-21-2 C₁₄H₁₇NOSi 
• 1259319-70-4 cyanomethyl 4-bromobenzoate 
• 176961-50-5 2-(4-bromophenyl)oxazole 

Relevant academic research and scientific papers

Facile one-pot synthesis of 2-oxazoline

We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to 5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials.

Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones

The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.

Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies

A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.

Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-Methyleneisochroman-1-ones

We report herein a ruthenium-catalyzed, oxazoline-directed strategy for C-H allylation of aryl oxazolines using allylic alcohols as the coupling partner. The present transformation unravels the unusual reactivity of allylic alcohols in the synthesis of 4-

Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization

A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo

AZAINDOLE DERIVATIVE HAVING AMPK-ACTIVATING EFFECT

Disclosed is a compound which is useful as an AMPK activator. A compound represented by formula: or its pharmaceutically acceptable salt, wherein X is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted heterocyclyl; R1 is hydrogen, halogen, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted acyl, substituted or unsubstituted carbamoyl, substituted or unsubstituted alkylthio, substituted or unsubstituted alkylsulfinyl, substituted or unsubstituted alkylsulfonyl, or substituted or unsubstituted alkyloxycarbonyl; R2 is halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like; R3 is halogen, hydroxy, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like; and R4 is hydrogen, halogen, hydroxy, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or the like.

Highly efficient synthesis of β-nitrate ester carboxamides through the ring-opening of 2-oxazolines

A novel method for the synthesis of β-nitrate ester carboxamides using non-corrosive tert-butyl nitrite (TBN) as the nitro source and easily available oxygen as the oxidant has been developed. Variously substituted 2-oxazolines were efficiently ring-opened to deliver the corresponding products in excellent yields. Notably, this reaction provides fast access to pharmaceuticals such as nicorandil.

A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)

The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)

Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines

We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami

A Mild and Regioselective Route to Functionalized Quinazolines

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.