70-11-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromoacetophenone is used as a research chemical and pharmaceutical intermediate for the development of drugs targeting human liver aldehyde dehydrogenase isoenzymes E1 and E2. Its irreversible inactivation property makes it a valuable tool in studying enzyme function and potential therapeutic applications.
Used in Chemical Synthesis:
2-Bromoacetophenone is used in the preparation of crystalline esters from acids. Its reactivity and functional group make it a versatile building block for the synthesis of various organic compounds, particularly in the field of organic chemistry.
Used in Enzyme Inhibition Studies:
2-Bromoacetophenone is employed as an inhibitor of neutral protein tyrosine phosphatases, which are important enzymes involved in cellular signaling pathways. Its inhibitory activity is useful in understanding the role of these enzymes in various biological processes and may lead to the development of targeted therapies for related diseases.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5796, 1954 DOI: 10.1021/ja01651a061Organic Syntheses, Coll. Vol. 2, p. 480, 1943Synthetic Communications, 22, p. 1923, 1992 DOI: 10.1080/00397919208021322

Air & Water Reactions

Reacts slowly with moisture in air to form hydrogen bromide.

Reactivity Profile

2-Bromoacetophenone reacts slowly with metals causing mild corrosion.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Purification Methods

Crystallise the bromide from EtOH, MeOH or pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 649.]

InChI:InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 123-91-1 1,4-dioxane 
• 98-86-2 acetophenone 
• 530-48-3 1,1-Diphenylethylene 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 98-85-1 1-Phenylethanol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 98-81-7 1-bromovinylbenzene 
• 704-77-8 (E)-3-Bromo-3-phenyl-acrylic acid 
• 2684-02-8 benzenediazonium 
• 60-29-7 diethyl ether 
• 22024-99-3 2-nitrobenzenesulfenyl bromide 
• 506-68-3 bromocyane 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 779-52-2 1-phenyl-2-piperidin-1-yl-ethanone 
• 779-53-3 4-morpholinylacetophenone 
• 5443-06-1 1,1'-diphenyl-2,2'-piperazine-1,4-diyl-bis-ethanone 
• 109442-08-2 1-methyl-1-phenacyl-hexahydro-azepinium; bromide 
• 6273-61-6 1-ethyl-1-phenacyl-piperidinium; bromide 
• 6276-59-1 4-methyl-4-phenacyl-morpholinium; bromide 
• 41298-85-5 2-(4-methylpiperazin-1-yl)-1-phenylethan-1-one 
• 109262-65-9 1-methyl-1-phenacyl-octahydro-azocinium; bromide 
• 106739-38-2 2-(4-ethyl-piperazino)-1-phenyl-ethanone 
• 110704-59-1 (4-phenylthiazol-2-yl)methyl benzoate 
• 16883-69-5 N-phenacylpyridinium bromide 
• 101353-65-5 2-(4-isopropyl-piperazino)-1-phenyl-ethanone 
• 5653-11-2 α-(1,2,3,4-Tetrahydro-2-isochinolyl)-acetophenon 
• 5304-34-7 2-(3-thiazolium)-1-phenylethanone bromide 

Relevant academic research and scientific papers

Simultaneous multistep synthesis using polymeric reagents

A synthesis was accomplished involving three transformations using three different polymeric reagents simultaneously in one reaction vessel to afford 2-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-1-pheny lethanone (4).

Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein

An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.

A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions

A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.

1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative difunctionalization of styrenes: Microfluidic synthesis of pentafluorophenoxy ketone

A practical and mild synthesis of pentafluorophenoxy ketone in a continuous flow microfluidic reactor has been developed through 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative coupling of styrenes with pentafluorophenol. Moreover, a series of pentafluorophenoxy ketone products were provided in moderate to good yields under metal-free conditions. A magnifying continuous flow system was erected to verify the appliance of this method.

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.

Thiazole ring-containing amide compounds as well as preparation method and application thereof

The invention discloses thiazole ring-containing amide compounds as well as a preparation method and application thereof, and belongs to the field of chemical technologies and pesticides. According to the present invention, p-phenylenediamine is adopted as a raw material to synthesize a series of the thiazole ring-containing amide compounds, and the synthesized thiazole ring-containing amide compounds have good inhibition effects on Xanthomonas oryzae pv.Oryza (Xoo), Xanthomonas oryzae pv.Oryzcola (Xoc) and Xanthomonas axonophora pv.Citri (Xac) in agricultural diseases and insect pests, and can be used for preparing the anti-plant bacterium agent.

Flexible on-site halogenation paired with hydrogenation using halide electrolysis

Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions

A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.