38418-24-5

Basic information

• Product Name: N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE
• Synonyms: 4-BROMOACETOACETANILIDE;AKOS B029155;CHEMBRDG-BB 5136053;N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE;4-BROMOACETOACETANILID;N-(4-bromophenyl)-3-oxobutanamide;3-oxo-N-(4'-broMophenyl)butanaMide
• CAS NO: 38418-24-5
• Molecular Formula: C₁₀H₁₀BrNO₂
• Molecular Weight: 256.1
• Mol File: 38418-24-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 137.5 °C
• Boiling Point: 417°Cat760mmHg
• Flash Point: 206°C
• Appearance: /
• Density: 1.516g/cm³
• Vapor Pressure: 3.66E-07mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• PKA: 11.00±0.46(Predicted)
• CAS DataBase Reference: N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE(38418-24-5)
• EPA Substance Registry System: N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE(38418-24-5)

Safety Data

• Hazardous Substances Data: 38418-24-5(Hazardous Substances Data)

Usage

General Description

N-(4-Bromo-phenyl)-3-oxo-butyramide is a chemical compound that belongs to the class of amides. It is formed by substituting the hydrogen atoms of butyramide with a 4-bromo-phenyl group and a ketone group at the third position. N-(4-BROMO-PHENYL)-3-OXO-BUTYRAMIDE is commonly used in organic synthesis, pharmaceuticals, and as a building block for the synthesis of other chemicals. It has potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents. Additionally, this compound may have uses in research and development, as well as in the production of specialty chemicals.

InChI:InChI=1/C10H10BrNO2/c1-7(13)6-10(14)12-9-4-2-8(11)3-5-9/h2-5H,6H2,1H3,(H,12,14)

Upstream product

• 106-40-1 4-bromo-aniline 
• 1118-84-9 allyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 141-97-9 ethyl acetoacetate 
• 542-08-5 isopropyl acetoacetate 
• 1694-31-1 tert-butyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 83999-07-9 C₁₆H₁₂BrN₄O₈^(1-)*C₆H₁₅N*H⁽¹⁺⁾ 
• 124841-20-9 3-Acetyl-1-(4-bromo-phenyl)-5-methylsulfanyl-1,3,3a,4,7,7a-hexahydro-1,4,6,7-tetraaza-inden-2-one; compound with trifluoro-acetic acid 
• 99757-52-5 N-(4-Bromo-phenyl)-2-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyramide 
• 151152-50-0 2-acetyl-3-anilino-acrylic acid-(4-bromo-anilide) 
• 23976-45-6 4-bromo-N-(4-bromophenyl)-3-oxobutanamide 
• 5463-29-6 6-bromo-2-hydroxyquinoline-4-carboxylic acid 
• 160534-32-7 (Z)-3-((4-bromophenyl)amino)-1-phenylprop-2-en-1-one 

Relevant articles and documents

Visible Light-Induced Pericyclic Cascade Reaction for the Synthesis of Quinolinone Derivatives with an Oxabicyclo[4.2.0]octene Skeleton

A photoinduced pericyclic cascade reaction has been developed to afford oxabicyclo[4.2.0]octenes. Mechanistic studies show that this reaction undergoes [2 + 2]-photocycloaddition, base-promoted elimination, retro-4π-electrocyclization, [1,5]-H shift, and

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst

A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.

On the Knorr synthesis of 6-bromo-4-methylquinolin-2(1H)-one

In the course of our work on infectious diseases, we were led to prepare 6-bromo-2-chloro-4-methylquinoline as a starting material. Since surprisingly little has been reported in the literature, the two synthetic steps to this compound were investigated. The synthesis involves a condensation between -keto esters and 4-bromoaniline and the cyclization of the resulting anilides into 6-bromoquinolin-2(1H)-one, otherwise known as the Knorr reaction. The 1H NMR monitoring of the first step allowed us to optimize the conditions leading specifically to the anilide without the occurrence of the alternative crotonate. To illustrate the scope of our finding, few additional anilides featuring electron-attracting groups were prepared. The study of their cyclization revealed some unsuspected steric effect governing this second step. Aside from rectifying a few claims in this chemistry, this study led to a three-step preparation of 6-bromo-2-chloro-4-methylquinoline in 48% overall yield from 4-bromoaniline. Georg Thieme Verlag Stuttgart - New York.