1665-47-0

Basic information

• Product Name: N-BENZYL-3-BROMOPROPANAMIDE
• Synonyms: N-BENZYL-3-BROMOPROPANAMIDE
• CAS NO: 1665-47-0
• Molecular Formula: C₁₀H₁₂BrNO
• Molecular Weight: 242.11
• Mol File: 1665-47-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 102-103 °C
• Boiling Point: 400.7°Cat760mmHg
• Flash Point: 196.1°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 1.25E-06mmHg at 25°C
• Refractive Index: 1.56
• PKA: 15.40±0.46(Predicted)
• CAS DataBase Reference: N-BENZYL-3-BROMOPROPANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-3-BROMOPROPANAMIDE(1665-47-0)
• EPA Substance Registry System: N-BENZYL-3-BROMOPROPANAMIDE(1665-47-0)

Safety Data

• Hazardous Substances Data: 1665-47-0(Hazardous Substances Data)

Usage

General Description

N-Benzyl-3-bromopropanamide is a chemical compound with the formula C11H13BrNO. It is a white to off-white solid with a molecular weight of 260.13 g/mol. N-BENZYL-3-BROMOPROPANAMIDE is primarily used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is a benzyl derivative of 3-bromopropanamide, making it useful in the production of other organic compounds. N-Benzyl-3-bromopropanamide is typically handled and stored in a cool, dry, well-ventilated area and should be kept away from heat, flame, and sources of ignition. Additionally, it should be protected from light and kept in a tightly closed container to prevent contamination or degradation.

InChI:InChI=1/C10H12BrNO/c11-7-6-10(13)12-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)

Upstream product

• 15486-96-1 3-Bromopropionyl chloride 
• 100-46-9 benzylamine 
• 7623-16-7 3-bromopropionyl bromide 

Downstream Products

• 13304-62-6 N-benzylacrylamide 
• 80578-25-2 3-benzyl-3,4,5,6-tetrahydro-2H-1,3-oxazine-2,4-dione 
• 470678-28-5 benzyl-(3-bromo-propionyl)-carbamic acid benzyl ester 
• 1244550-43-3 C₂₇H₂₂N₄O₅ 
• 60536-21-2 10-benzylacridine-9(10H)-one 
• 1243283-98-8 N-benzyl-3-[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]propanamide 
• 470677-97-5 benzyl-(3-bromo-1-trimethylsilanyloxy-propyl)-carbamic acid benzyl ester 
• 955031-15-9 2-(N-benzylcarbamoyl)ethyltriphenyliminophosphorane 
• 1013663-30-3 N-benzyl-3-azidopropanamide 

Relevant articles and documents

Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinoneviaintramolecular aza-Prins type reaction

A novel aza-Prins type cyclization reaction involvingN-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis of N-heterocyclic frameworks. Further, post-synthetic modification results in the unprecedented formation of its triazole, tetracyclic diazacyclopenta[def]phenanthrene-1,4(9a1H)-dione and carbonyl derivatives.

Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

Targeting mycobacterium protein tyrosine phosphatase B for antituberculosis agents

Protein tyrosine phosphatases are often exploited and subverted by pathogenic bacteria to cause human diseases. The tyrosine phosphatase mPTPB from Mycobacterium tuberculosis is an essential virulence factor that is secreted by the bacterium into the cytoplasm of macrophages, where it mediates mycobacterial survival in the host. Consequently, there is considerable interest in understanding the mechanism by which mPTPB evades the host immune responses, and in developing potent and selective mPTPB inhibitors as unique antituberculosis (antiTB) agents. We uncovered that mPTPB subverts the innate immune responses by blocking the ERK1/2 and p38 mediated IL-6 production and promoting host cell survival by activating the Akt pathway. We identified a potent and selective mPTPB inhibitor I-A09 with highly efficacious cellular activity, from a combinatorial library of bidentate benzofuran salicylic acid derivatives assembled by click chemistry. We demonstrated that inhibition of mPTPB with I-A09 in macrophages reverses the altered host immune responses induced by the bacterial phosphatase and prevents TB growth in host cells. The results provide the necessary proof-of-principle data to support the notion that specific inhibitors of the mPTPB may serve as effective antiTB therapeutics.