32664-14-5

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-BROMO-PHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-OXAZOLE is used as a potential substituent in the synthesis of new series of potent benzodiazepine γ-secretase inhibitors. The application reason is its potential use in the treatment of Alzheimer's disease, as these inhibitors can modulate the enzyme activity involved in the pathology of the condition.

Synthesis Reference(s)

Synthetic Communications, 26, p. 1335, 1996 DOI: 10.1080/00397919608003493

InChI:InChI=1/C11H12BrNO/c1-11(2)7-14-10(13-11)8-3-5-9(12)6-4-8/h3-6H,7H2,1-2H3

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 586-75-4 4-chlorobenzoyl chloride 
• 586-76-5 4-Bromobenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 19819-94-4 4-allyl-benzoic acid ethyl ester 
• 136527-43-0 2-(4-allyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 74029-45-1 4-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-benzaldehyde 
• 51849-98-0 1-[4-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-cycloheptanol 
• 132454-38-7 2-<4-(Bis-4-(methoxyphenyl)-hydroxymethyl)-phenyl>-4,4-dimethyl-1,3-oxazoline 
• 221238-61-5 2-<4-(vinyldimethylsilyl)phenyl>-4,4-dimethyloxazoline 
• 211388-40-8 4-chloro-α-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-benzenemethanol 
• 412317-51-2 5-[4-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-5-hydroxy-1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester 
• 219829-02-4 9-hydroxy-9-(4-carboxyphenyl)fluorene 
• 71888-33-0 C₁₆H₂₁⁽²⁾HN₂O₂ 
• 71888-26-1 5-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-3,3-diphenyl-1(3H)-isobenzofuranone 
• 132454-39-8 4-Carboxy-4',4''-dimethoxyphenylhydroxymethane 
• 132454-41-2 N-Succinimidyl-4--benzoate 
• 132454-40-1 N-succinimidyl-4--hydroxymethyl-benzoate 

Relevant academic research and scientific papers

Silicon-rhodamine isothiocyanate for fluorescent labelling

An efficient synthesis for silicon-rhodamines was developed, enabling the preparation and evaluation of silicon-rhodamine isothiocyanate (SITC) as a novel tool for facile fluorescent labeling. Ease of use in conjugation to amino groups, high stability and excellent photophysical properties are demonstrated. SITC-actin was found to be neutral to F-actin polymerization induction and well suited for high resolution fluorescence microscopy.

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Directed functionalization of halophenyl-2-oxazolines with TMPMgCl?LiCl

A variety of difunctionalized aryl-2-oxazolines were prepared from the reaction of halophenyl-2-oxazolines and TMPMgCl?LiCl to give an organomagnesium reagent, which was then treated with various electrophiles. The metalation step takes place under mild conditions, and this process al-lows for the isolation of the desired products in good yields. No isomeric or other benzyne-derived products were detected. The influence of the halogen substituents on the acidity of the aromatic hydrogen atoms was evaluated by using density functional theory (DFT) calculations.

Synthesis of 2-aryl/heteroaryloxazolines from nitriles under metaland catalyst-free conditions and evaluation of their antioxidant activities

The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.

A novel and direct synthesis of 1,3,4-oxadiazoles or oxazolines from carboxylic acids using cyanuric chloride/indium

Direct synthesis of various oxazolines and 1,3,4-oxadiazoles from carboxylic acids was achieved using cyanuric chloride/indium under very mild conditions.

Benzoheterocyclic derivatives

A benzoheterocyclic derivative of the following formula [1]: and pharmaceutically acceptable salts thereof, which show excellent anti-vasopressin activity, vasopressin agonistic activity and oxytocin antagonistic activity, and are useful as a vasopressin antagonist, vasopressin agonist or oxytocin antagonist.

Benzoheterocyclic derivatives

PCT No. PCT/JP95/01124 Sec. 371 Date Nov. 13, 1996 Sec. 102(e) Date Nov. 13, 1996 PCT Filed Jun. 7, 1995 PCT Pub. No. WO95/34540 PCT Pub. Date Dec. 21, 1995A benzoheterocyclic derivative of the following formula [1]: and pharmaceutically acceptable salts

Positional isomers and analogs of mazindol as potential inhibitors of the cocaine binding site on the dopamine transporter site

A series of compounds, where the keto-tautomeric form of mazindol (2b) was modified by placing the 2-(p-chlorobenzoyl) portion of the molecule in the 3- and 4-positions, substituting the imidazo ring A by a 4,4-dimethyl 1- 2-oxazolo ring, and replacing th

A facile one stage synthesis of oxazolines under microwave irradiation

A rapid, high yielding procedure for the synthesis of 2-substituted oxazolines has been achieved under microwave irradiation from alkyl and aryl nitriles and β-amino alcohols using a mild Lewis acid catalyst.