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Usage

Uses

Used in Pharmaceutical Industry:
3-bromopropiophenone is utilized as an intermediate in the synthesis of various pharmaceuticals. Its chemical properties make it a valuable component in the development of new drugs and medications, contributing to the advancement of healthcare and medical treatments.
Used in Agrochemical Industry:
In the agrochemical sector, 3-bromopropiophenone serves as an intermediate in the production of agrochemicals. This involvement is crucial for the development of pesticides, herbicides, and other agricultural products that are essential for maintaining crop health and productivity.
Used in Fragrance Industry:
3-bromopropiophenone is employed as a component in the creation of fragrances due to its sweet, floral scent. It adds depth and complexity to perfumes, colognes, and other scented products, enhancing the sensory experience for consumers.
Used in Flavoring Industry:
3-bromopropiophenone also finds application in the flavoring industry, where it is used to impart specific tastes and aromas to food and beverages. Its distinct properties allow it to contribute to the overall flavor profile of various products, adding to their appeal and enjoyment.
Safety Precautions:
Given the hazardous nature of 3-bromopropiophenone, it is imperative that it be handled and stored with caution. It should be kept in well-ventilated areas to minimize the risk of flammability and exposure. Additionally, personal protective equipment, such as gloves, goggles, and masks, should be worn when working with this chemical to protect against skin, eye, and respiratory irritation.

InChI:InChI=1/C9H9BrO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 15486-96-1 3-Bromopropionyl chloride 
• 71-43-2 benzene 
• 768-03-6 Phenyl vinyl ketone 
• 590-92-1 3-Bromopropionic acid 
• 38858-73-0 1-phenyl-1-trimethylsiloxycyclopropane 
• 29526-96-3 1-phenylcyclopropan-1-ol 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 637-59-2 1-Bromo-3-phenylpropane 
• 93-89-0 benzoic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 13735-81-4 1-styrenyloxytrimethylsilane 

Downstream Products

• 73-63-2 1-phenyl-3-(piperidin-1-yl)propan-1-one 
• 115308-40-2 dimethyl-(3-oxo-3-phenyl-propyl)-sulfonium ; bromide 
• 100306-31-8 3-bromo-1-phenyl-1-propanol 
• 14066-85-4 piperidine hydrobromide 
• 28918-16-3 1-(1-imidazolyl)-3-phenyl-propan-3-one 
• 101023-55-6 imidazole hydrobromide 
• 78909-77-0 2-(β-Benzoylethyl)thio-3-amino-6-chloropyridine 
• 78909-76-9 2-(β-Benzoylethyl)thio-3-(β-benzoylethyl)amino-6-chloropyridine 
• 78909-74-7 2-(β-Benzoylethyl)thio-3-ureido-6-chloropyridine 
• 115901-62-7 N-Benzyl-2-[(3-oxo-3-phenyl-propyl)-(toluene-4-sulfonyl)-amino]-acetamide 
• 115901-63-8 N,N-Dimethyl-2-[(3-oxo-3-phenyl-propyl)-(toluene-4-sulfonyl)-amino]-acetamide 
• 69689-02-7 β(Butylthio)propiophenone 
• 85350-64-7 1-(3-oxo-3-phenylpropyl)-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine 
• 85208-95-3 N-(β-Benzoylethyl)-N-tosyl-3-aminomethylpyridin 

Relevant academic research and scientific papers

Stepwise benzylic oxygenation via uranyl-photocatalysis

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: Syntheses of medium-sized heterocycles

The synthesis of medium-sized heterocycles possessing a trans double bond is still a challenge. Herein, gold(I)-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade reaction of furans has been developed, providing highly efficient access to ten- and eleven-membered heterocycles with a broad substrate scope under mild reaction conditions. The reaction outcome features high chemoselectivity at the C5-position of furan. Moreover, a trans-double bond was embodied in the medium ring system.

Anodic cyclization of dimethyl 2-(3-Oxo-3-arylpropyl) malonates into the corresponding dimethyl 2-aroylcyclopropane-1,1-dicarboxylates

A variety of dimethyl 2-(3-oxo-3-arylpropyl)malonates were electrooxidized in methanol, in the presence of potassium iodide and a base or a neutral salt, to give the corresponding cyclized dimethyl 2-aroylcyclopropane-1,1- dicarboxylates in moderate to good yields. The reactions were carried out under extremely mild reaction conditions, in which the optimal amount of electrolytic current varied from 2.12-2.41 F·mol-1 depending on the substrates. The reaction presumably proceeds via a two-electron oxidation process, in which iodide ions play an important role as the electron carrier between the anode and the substrate. Georg Thieme Verlag Stuttgart. New York.

Azido carbonyl compounds as DNA cleaving agents

Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.

Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade

A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities. Georg Thieme Verlag Stuttgart - New York.

Direct asymmetrie catalytic thienylaluminum addition to ketones: A concise approach to the synthesis of (S)-tiemonium iodide

A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.

An efficient and general approach to β-functionalized ketones

Figure presented The oxidation of selected anlons (N3 -, SCN-, I-, and Br-) by eeric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to β-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.