148836-24-2

Basic information

• Product Name: (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE
• Synonyms: (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE;(4S)-2-(2-Bromophenyl)-4,5-dihydro-4-isopropyloxazole
• CAS NO: 148836-24-2
• Molecular Formula: C₁₂H₁₄BrNO
• Molecular Weight: 268.15
• Mol File: 148836-24-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE(148836-24-2)
• EPA Substance Registry System: (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE(148836-24-2)

Safety Data

• Hazardous Substances Data: 148836-24-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE is used as a key intermediate in pharmaceutical research for the development of new drugs and pharmaceuticals. Its unique structure and chirality may offer advantages in the design and synthesis of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-(2-BROMOPHENYL)-4-ISOPROPYL-4,5-DIHYDROOXAZOLE serves as a valuable building block for the creation of more complex molecules. Its bromophenyl and isopropyl substituents can be further functionalized or used as starting points for the synthesis of various organic compounds.

Upstream product

• 4001-73-4 2-Bromobenzamide 
• 2026-48-4 (S)-valinol 
• 88-65-3 2-bromobenzoic-acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1340476-85-8 (4S)-4,5-dihydro-2-{2'-[(R)-1-(1-naphthyl)ethylamino]phenyl}-4-isopropyloxazole 
• 1340476-93-8 (4S)-4,5-dihydro-2-[2'-(2,6-diisopropylanilino)phenyl]-4-isopropyloxazole 
• 1340476-81-4 (4S)-4,5-dihydro-2-{2'-[(R)-α-methylbenzylamino]phenyl}-4-isopropyloxazole 
• 1340476-99-4 (4S)-4,5-dihydro-2-[2'-(benzamido)phenyl]-4-isopropyloxazole 
• 1340476-89-2 (4S)-4,5-dihydro-2-[2'-(2,6-dimethylanilino)phenyl]-4-isopropyloxazole 
• 1340477-03-3 (4S)-4,5-dihydro-2-{2'-[(S)-tert-butylsulfinamido]phenyl}-4-isopropyloxazole 
• 1374010-10-2 C₃₀H₃₃N₂O₃P 
• 180260-74-6 (S)-2-[2-(dicyclohexylphosphino)phenyl]-4-i-propyloxazoline 
• 1609167-95-4 (4S)-4,5-dihydro-2-(2′-(4-methoxyanilino)phenyl)-4-isopropyloxazole 
• 1609167-96-5 (4S)-4,5-dihydro-2-(2′-(2-phenoxyanilino)phenyl)-4-isopropyloxazole 

Relevant articles and documents

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.

Sulfoxide ligand metal catalyzed oxidation of olefins

The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

Preparation of Aryl(dicyclohexyl)phosphines by C-P Bond-Forming Cross-Coupling in Water Catalyzed by an Amphiphilic-Resin-Supported Palladium Complex

Aryl(dicyclohexyl)phosphines were prepared by a catalytic C-P bond-forming cross-coupling reaction of haloarenes with dicyclohexylphosphine under heterogeneous conditions in water containing an immobilized palladium complex coordinated to an amphiphilic polystyrene-poly(ethylene glycol) resin supported di(tert -butyl)phosphine ligand.

Enantioselective Allylic C?H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C?H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sul

Ring-opening polymerization of rac-lactide with aluminum chiral anilido-oxazolinate complexes

A series of dimethylaluminum complexes (L1a-i)AlMe2 (2a-i, where HL1a-i = 2-(2′-ArNH)phenyl-4-R1- oxazoline) bearing chiral, bidentate anilido-oxazolinate ligands have been prepared and characterized. Six of the

Bis(perfluoroalkyl) phosphino-oxazoline: A modular, stable, strongly π-accepting ligand for asymmetric catalysis

A new class of stable, strongly π-accepting and modular bis-(perfluoroalkyl)-phosphine-oxazoline ligands (FOX) as CO mimics was prepared. It was demonstrated that these ligands, when coordinated to palladium catalysts, promote the asymmetric alkylation of monosubstituted allyl substrates with excellent regio- and enantioselectivity. Solid and solution structure analysis of the FOX-ligated Pd-allyl intermediate reveals that the combination of relative steric and strong trans influences presented by the P(CF 3)2 moiety gave rise to the excellent selectivity.

The synthesis of phosphine oxide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation

The phosphine oxide-linked bis(oxazoline) ligands were designed and synthesized in two ways. One is the coupling of Grignard reagent derived from 2-(2-bromophenyl)oxazoline with phenylphosphonic dichloride, another route is the condensation of bis(2-formylphenyl)(phenyl)phosphine oxide with chiral amino alcohols followed by NBS oxidation. These new bis(oxazoline) ligands were applied in Pd-catalyzed asymmetric allylic alkylation reactions and good yields and enantioselectivities were obtained with diphenyl substituted ligand (up to 95% ee).

Modular synthesis of chiral β-diketiminato-type ligands containing 2-oxazoline moiety via palladium-catalyzed amination

A family of new chiral β-diketiminato-type ligands containing oxazoline moiety has been synthesized in moderate to high yields (typically 30-95%) via a Pd-catalyzed amination reaction of chiral oxazolines with primary amines and amides. Notably, (S)-tert-

Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines

A series of enantiomerically pure 2-[2-(diarylphosphino)aryl]-oxazolines was prepared from commercially available or synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid (ii) ZnCl2 catalyzed condensation with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorous were prepared by either diastereoselective nucleophilic substitution of halogenide of Ar1Ar2PCl or by nucleophilic aromatic substitution with LiPAr1Ar2. In addition, sulfur and selenium analogs were prepared.