6653-71-0

Basic information

• Product Name: N-benzyl-2-bromo-propanamide
• Synonyms: N-benzyl-2-bromo-propanamide;2-BROMO-N-BENZYL-PROPANAMIDE;Ccris 1819;N-Benzyl-2-bromopropionamide;Propionamide, N-benzyl-2-bromo-;N-benzyl-2-bromopropanamide(SALTDATA: FREE)
• CAS NO: 6653-71-0
• Molecular Formula: C₁₀H₁₂BrNO
• Molecular Weight: 242.12
• Mol File: 6653-71-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 380.4°C at 760 mmHg
• Flash Point: 183.9°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 5.45E-06mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: N-benzyl-2-bromo-propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-2-bromo-propanamide(6653-71-0)
• EPA Substance Registry System: N-benzyl-2-bromo-propanamide(6653-71-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6653-71-0(Hazardous Substances Data)

Usage

General Description

N-benzyl-2-bromo-propanamide is a chemical compound that is a derivative of propanamide, containing a benzyl group and a bromine atom. It is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds. N-benzyl-2-bromo-propanamide has potential applications in the development of drugs for various therapeutic purposes. However, it is important to handle this chemical with caution, as it can be harmful if it comes into contact with the skin, eyes, or respiratory system. It should be stored and used in a well-ventilated area and with the appropriate personal protective equipment to ensure safety.

InChI:InChI=1/C10H12BrNO/c1-8(11)10(13)12-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13)

Upstream product

• 563-76-8 α-bromopropionyl bromide 
• 100-46-9 benzylamine 
• 598-72-1 2-Bromopropionic acid 
• 535-11-5 Ethyl 2-bromopropionate 
• 7148-74-5 2-Bromopropionyl chloride 

Downstream Products

• 122885-43-2 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-(1-benzylcarbamoyl-ethyl) ester 1-tert-butyl ester 
• 122885-45-4 2-tert-Butoxycarbonylamino-2-methyl-propionic acid 1-benzylcarbamoyl-ethyl ester 
• 124371-71-7 N?benzyl?2?phenoxypropanamide 
• 79658-55-2 3-benzyl-5-methyl-1,3-oxazolidine-2,4-dione 
• 10264-12-7 N-benzylpropanamide 
• 103808-45-3 (S)-N-benzyl-2-hydroxypropionamide 
• 131432-92-3 (S)-(-)-2-bromo-N-benzylpropanamide 
• 815624-56-7 C₁₆H₁₆ClNO₂ 
• 109725-05-5 N,N-phthaloyl-DL-alanine-benzylamide 

Relevant articles and documents

Novel Functionalized Amino Acids as Inhibitors of GABA Transporters with Analgesic Activity

Neuropathic pain resistance to pharmacotherapy has encouraged researchers to develop effective therapies for its treatment. γ-Aminobutyric acid (GABA) transporters 1 and 4 (mGAT1 and mGAT4) have been increasingly recognized as promising drug targets for neuropathic pain (NP) associated with imbalances in inhibitory neurotransmission. In this context, we designed and synthesized new functionalized amino acids as inhibitors of GABA uptake and assessed their activities toward all four mouse GAT subtypes (mGAT1-4). According to the obtained results, compounds 2RS,4RS-39c (pIC50 (mGAT4) = 5.36), 50a (pIC50 (mGAT2) = 5.43), and 56a (with moderate subtype selectivity that favored mGAT4, pIC50 (mGAT4) = 5.04) were of particular interest and were therefore evaluated for their cytotoxic and hepatotoxic effects. In a set of in vivo experiments, both compounds 50a and 56a showed antinociceptive properties in three rodent models of NP, namely, chemotherapy-induced neuropathic pain models (the oxaliplatin model and the paclitaxel model) and the diabetic neuropathic pain model induced by streptozotocin; however compound 56a demonstrated predominant activity. Since impaired motor coordination is also observed in neuropathic pain conditions, we have pointed out that none of the test compounds induced motor deficits in the rotarod test.

Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids

We herein report an enantioselective palladium-catalyzed cross-coupling between α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of α-bromo carbonyl compounds.

Microwave-assisted synthesis of triazole derivatives conjugated with piperidine as new anti-enzymatic agents

The current study was aimed for the study of piperidine-based triazole compounds for their biological potential against various enzymes. A novel library of compounds, 9a-r, having piperidine, 1,2,4-triazole, and propanamides was synthesized through consecutive steps including the formation of sulfonamide, hydrazide, 1,2,4-triazole, and thio-ether. Initially, 4-methoxybenzenesulfonyl chloride (1) and ethyl isonipecotate (2) were utilized to develop ethyl 1-(4-methoxyphenylsulfonyl)-4-piperidinecarboxylate (3). The product 3 was converted into respective hydrazide (4) which was further cyclized into 1,2,4-triazole (5) nucleus. A series of propanamides, 8a-r, were synthesized from different amines, 6a-r. These electrophiles, 8a-r, were reacted with compound 5 under conventional and microwave-assisted protocols to acquire the library of hybrids, 9a-r. The structural confirmations were availed by 1H-NMR, 13C-NMR, and IR techniques. The whole series was evaluated for biological potential against acetylcholinesterase (AChE) and α-glucosidase enzymes. The biological evaluation ranges low to high in potential for different compounds based on the structural variations of synthesized compounds. Almost all the compounds remained active against both the enzymes except a few ones. The bovine serum albumin (BSA) binding study demonstrated the flow of drug in the body, and the docking study explained the interactions responsible for active behavior of synthesized compounds.