7194-78-7

Basic information

• Product Name: 2-(3-broMophenyl)-2-oxoacetic acid
• Synonyms: 2-(3-broMophenyl)-2-oxoacetic acid
• CAS NO: 7194-78-7
• Molecular Formula: C₈H₅BrO₃
• Molecular Weight: 229.0275
• Mol File: 7194-78-7.mol

Chemical Properties

• Melting Point: 60-61 °C
• Boiling Point: 329.4±34.0 °C(Predicted)
• Appearance: /
• Density: 1.738±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.10±0.54(Predicted)
• CAS DataBase Reference: 2-(3-broMophenyl)-2-oxoacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-broMophenyl)-2-oxoacetic acid(7194-78-7)
• EPA Substance Registry System: 2-(3-broMophenyl)-2-oxoacetic acid(7194-78-7)

Safety Data

• Hazardous Substances Data: 7194-78-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(3-Bromophenyl)-2-oxoacetic acid is utilized as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical entities through reactions such as coupling, substitution, and condensation.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(3-Bromophenyl)-2-oxoacetic acid is employed as a building block for the development of novel pharmaceuticals. Its potential applications include the synthesis of drugs targeting various therapeutic areas, such as central nervous system disorders, cardiovascular diseases, and oncology.
Used in Agrochemical Development:
2-(3-Bromophenyl)-2-oxoacetic acid may also find applications in the agrochemical sector, where it can be used as a precursor for the synthesis of new pesticides, herbicides, or other crop protection agents. Its unique chemical properties can contribute to the development of more effective and environmentally friendly agrochemicals.
Used in Chemical Research and Development:
Furthermore, 2-(3-Bromophenyl)-2-oxoacetic acid has potential uses in chemical research and development. It can be employed as a model compound to study various chemical reactions and mechanisms, contributing to the advancement of synthetic chemistry and the discovery of new chemical processes.

Upstream product

• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 62123-80-2 ethyl 2-(3-bromo-phenyl)-2-oxo-acetate 
• 49839-81-8 3-bromomandelic acid 

Downstream Products

• 1071454-55-1 {3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-oxo-acetic acid 
• 585-76-2 m-bromobenzoic acid 
• 101763-98-8 S-(4-chlorophenyl) 3-bromobenzothioate 
• 99515-46-5 S-phenyl 3-bromobenzothioate 
• 81316-36-1 methyl (m-bromophenyl)glyoxylate 
• 25023-37-4 (E)-1-(3-bromophenyl)-3-phenylprop-2-en-1-one 

Relevant articles and documents

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Hypervalent Iodine(III)-Promoted Radical Oxidative C-H Annulation of Arylamines with α-Keto Acids

A novel catalyst-free radical oxidative C-H annulation reaction of arylamines with α-keto acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A.

Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition

We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3C?:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.

Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions

Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is

Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis

A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins.

METHOD FOR PRODUCING BENZOYL FORMIC ACID COMPOUND AND PYRIDAZINE COMPOUND

The present invention provides an industrially-advantageous process for preparing a benzoyl formic acid compound, and an efficient process for preparing a pyridazine compound using the same process. Specifically, the present invention provides a process for preparing a compound represented by formula (2), which comprises a step (B): a step of reacting a compound represented by formula (1) with a nitrosyl sulfuric acid in water to produce the compound represented by formula (2).

Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid

The invention relates to a novel synthesis method of a benzene ring polysubstituted compound based on benzoyl formic acid. According to the synthesis method, an acetophenone-based benzene ring polysubstituted compound is used as a raw material, a specific

Tandem N, N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate

Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative.

Palladium-Catalyzed Primary Amine-Directed Decarboxylative Annulation of α-Oxocarboxylic Acids: Access to Indolo[1,2-a]quinazolines

An efficient protocol for the preparation of indolo[1,2-a]quinazolines via palladium-catalyzed decarboxylative annulation of indols with α-oxocarboxylic acids has been realized by using primary amine as a directing group (DG). This transformation proceeds smoothly with exclusive regioselectivity and represents an one-pot Domino synthesis of indo-lo[1,2-a]quinazolines from α-oxocarboxylic acids. (Figure presented.).

Electrochemical synthesis of enaminones: Via a decarboxylative coupling reaction

An environmentally benign and efficient electrochemical synthesis of enaminones via a decarboxylative coupling reaction of α-keto acids using n-Bu4NI as a redox catalyst and electrolyte under constant current electrolysis in an undivided cell is reported. A broad vinyl azide substrate scope and high functional group tolerance are observed. A gram-scale reaction further demonstrates the practicability of the protocol. The results of cyclic voltammetry and control experiments indicate that I2 is likely the active species to initiate the oxidative decarboxylation via an acyl hypoiodite intermediate.