20201-26-7

Basic information

• Product Name: Ethyl 4-bromobenzoylformate
• Synonyms: BENZENEACETIC ACID, 4-BROMO-A-OXO-, ETHYL ESTER;Ethyl p-bromophenylglyoxylate;ETHYL 4-(BROMOPHENYL)GLYOXALATE;ETHYL 4-BROMOPHENYLGLYOXYLATE;ETHYL 4-BROMOBENZOYL FORMATE;Ethyl 2-(4-bromophenyl)-2-oxoacetate;4-BROMOBENZOYLFORMICACIDETHYLESTER;Benzeneacetic acid, 4-broMo-α-oxo-, ethyl ester
• CAS NO: 20201-26-7
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08
• Mol File: 20201-26-7.mol

Chemical Properties

• Boiling Point: 322°C
• Flash Point: 149°C
• Appearance: /
• Density: 1.480
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Ethyl 4-bromobenzoylformate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-bromobenzoylformate(20201-26-7)
• EPA Substance Registry System: Ethyl 4-bromobenzoylformate(20201-26-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 20201-26-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-bromobenzoylformate is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications. Its chemical properties make it a valuable component in the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Ethyl 4-bromobenzoylformate serves as an intermediate in the production of agrochemicals, which are essential for enhancing crop protection and improving agricultural yields.
Used in Organic Synthesis:
Ethyl 4-bromobenzoylformate is employed as a building block in organic synthesis, allowing for the construction of complex organic molecules that can be used in various applications, including the development of new materials and compounds.
Used in Chemical Reactions as a Reagent:
Ethyl 4-bromobenzoylformate also functions as a reagent in chemical reactions, facilitating specific transformations and processes that are vital for the synthesis of target molecules in research and industrial applications.

InChI:InChI=1/C10H9BrO3/c1-2-14-10(13)9(12)7-3-5-8(11)6-4-7/h3-6H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 106-37-6 1.4-dibromobenzene 
• 95-92-1 oxalic acid diethyl ester 
• 5467-74-3 4-Bromophenylboronic acid 
• 623-49-4 ethyl cyanoformate 
• 14367-97-6 1-(4-bromophenyl)-2-nitro-1-ethanone 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 140-89-6 potassium ethyl xanthogenate 
• 99-90-1 para-bromoacetophenone 
• 14062-25-0 Ethyl 4-bromophenylacetate 
• 73387-60-7 1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 
• 108-86-1 bromobenzene 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 78597-73-6 [3-(4-Bromo-phenyl)-2-oxo-2H-benzo[1,4]oxazin-6-yl]-acetic acid methyl ester 
• 78587-68-5 2-[3-(4-Bromo-phenyl)-2-oxo-2H-benzo[1,4]oxazin-6-yl]-propionic acid methyl ester 
• 250602-68-7 ethyl (Z)-2-(4-bromophenyl)-2-(hydroxyimino)acetate 
• 250602-67-6 ethyl (E)-2-(4-bromophenyl)-2-(hydroxyimino)acetate 
• 30565-53-8 ethyl 2-(4-bromophenyl)-2-hydroxyacetate 
• 731018-45-4 2-(4-bromo-phenyl)-3-cyclohexyl-acrylic acid ethyl ester 
• 92294-28-5 Cyclohexyl-<4-brom-phenyl>-glykolsaeure 
• 805191-30-4 Cyclohexyl-<4-brom-phenyl>-glykolsaeure-<2-diaethylamino-aethylester> 
• 1013910-55-8 (R)-(-)-ethyl 2-(4-bromophenyl)-2-hydroxy-3-nitropropanoate 
• 21453-02-1 3-(4-bromophenyl)quinoxalin-2(1H)-one 
• 917085-52-0 3-(4-bromophenyl)-2H-benzo[b][1,4]oxazin-2-one 
• 30809-08-6 (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl (4-bromophenyl)(oxo)acetate 
• 1393357-67-9 1,5-bis(2,2-bis((3,7-dimethyloctyl)oxy)ethyl)-3,7-bis (4-bromophenyl)dipyrrolo[2,3-b:2',3'-e]pyrazine-2,6(1H,5H)-dione 
• 1429317-16-7 (R)-tert-butyl 3-(1-(4-bromophenyl)-2-ethoxy-1-hydroxy-2-oxoethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 

Relevant articles and documents

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, o-Quinone Methides, and Dialkyl Phosphites

A highly regio- and diastereoselective approach for the synthesis of phosphate substituted dihydrocoumarins via Br?nsted base catalyzed [1,2]-phospha-Brook rearrangement is reported. The two-step, one-pot Michael addition of α-phosphonyloxy enolates proceeds by coupling of dialkyl phosphite and α-ketoesters to o-quinone methides, followed by an intramolecular cyclization, providing 3,4-dihydrocoumarin frameworks.

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade

A novel P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones has been developed that affords a facile synthesis of functionalized pyrrolidines in moderate to excellent yields with exclusive chemoselectivity and high diastereoselectivity. Mechanistic investigation reveals that the reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade. The reaction herein also represents the first study of the reactivity patterns of the Kukhtin-Ramirez adducts toward ambiphilic nucleophile-electrophiles.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group

Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB1 receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.