5339-26-4

Basic information

• Product Name: 4-Nitrophenethyl bromide
• Synonyms: P-NITROPHENETHYL BROMIDE;BENZENE, 1-(2-BROMOETHYL)-4-NITRO-;1-(2-BROMOETHYL)-4-NITROBENZENE;2-(4-NITROPHENYL)-1-BROMOETHANE;2-(4-NITROPHENYL)ETHYL BROMIDE;4-(NITROPHENYL)ETHYL BROMIDE;4-NITROPHENETHYL BROMIDE;1-Bromo-2-(4-nitrophenyl)ethane
• CAS NO: 5339-26-4
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.06
• EINECS: 226-271-7
• Mol File: 5339-26-4.mol

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 116°C/0.2mm
• Flash Point: 116°C/0.2mm
• Appearance: Yellow/Adhering Crystals or Crystalline Powder
• Density: 1.6270 (rough estimate)
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform(Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in water (partly) and methanol.
• BRN: 1909321
• CAS DataBase Reference: 4-Nitrophenethyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenethyl bromide(5339-26-4)
• EPA Substance Registry System: 4-Nitrophenethyl bromide(5339-26-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37-24/25
• WGK Germany: 3
• Hazardous Substances Data: 5339-26-4(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
4-Nitrophenethyl bromide is used as a GST T1-1 substrate for identifying many kinetic parameters (Km, Kcat) for hGST T1-1 variants. This application is crucial in the study of enzyme kinetics and understanding the behavior of various enzyme variants.
Used in Chemical Synthesis:
As an electrophile, 4-Nitrophenethyl bromide can be utilized in various chemical synthesis processes, particularly in the formation of new compounds through reactions with nucleophiles.
Used in Pharmaceutical Industry:
4-Nitrophenethyl bromide may also find applications in the pharmaceutical industry, where it can be used as a building block or intermediate in the synthesis of various drugs and pharmaceutical compounds.
Used in Environmental Analysis:
In environmental analysis, 4-Nitrophenethyl bromide could be employed as a reference compound or standard for the detection and quantification of similar electrophilic pollutants in environmental samples.

Biochem/physiol Actions

4-Nitrophenethyl bromide is used as a marker in for the θ-class of glutathione S-transferases (GSTs). It activates the human θ-class glutathione transferase T1-1 enzyme.

InChI:InChI=1/C8H8BrNO2/c9-6-5-7-1-3-8(4-2-7)10(11)12/h1-4H,5-6H2

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 100-12-9 4-ethylnitrobenzene 
• 100-13-0 4-nitrostyrene 
• 60-12-8 2-phenylethanol 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 104-03-0 4-nitrobenzeneacetic acid 
• 100-27-6 2-(4-nitrophenyl)ethanol 

Downstream Products

• 101496-66-6 2,5-dimethyl-1-(4-nitro-phenethyl)-piperidin-4-one 
• 101291-45-6 N-<2-(4-nitrophenyl)ethyl>phthalimide 
• 119438-76-5 rac-17-(4-nitro-phenethyl)-morphinane 
• 101603-37-6 ethyl 2-(N-acetamido)-2-(carboxyethyl)-4-(4-nitrophenyl)butanoate 
• 52118-15-7 N-Methyl-β-(p-nitrophenyl)-β'-phenyldiaethylamin 
• 91098-69-0 1-[2-(4-nitrophenyl)ethyl]piperazine 
• 73997-48-5 N-(β-p-nitrophenylethyl)quinuclidinium bromide 
• 73997-51-0 N-(β-p-nitrophenylethyl)-1,4-diazabicyclo<2.2.2>octanium bromide 
• 73997-52-1 N-(β-p-nitrophenylethyl)-3-hydroxyquinuclidinium bromide 
• 73997-50-9 N-(β-p-nitrophenylethyl)-3-chloroquinuclidinium bromide 
• 100-13-0 4-nitrostyrene 
• 83967-66-2 3-Hydroxy-1-[2-(4-nitro-phenyl)-ethyl]-1-azonia-bicyclo[2.2.2]octane; perchlorate 
• 138557-88-7 1,3-dimethyl-6-[4-(2-[4-nitrophenyl]ethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione 
• 101472-06-4 (3R,4S)-(+)-cis-3-methyl-1-<2-(4-nitrophenyl)ethyl>-N-phenyl-4-piperidinamine 

Relevant articles and documents

Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

To improve access to a key synthetic intermediate we targeted a direct hydrobromination-Negishi route. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed. Re-examination of early reports revealed that selective Markovnikov addition, often simply termed "normal" addition, is not always observed with HBr unless air is excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol.

Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using

Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacyclcododecane-N,N′,N″,N′″-tetraacetic acid compounds with a pendant amino or hydroxyl group, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

Synthesis and biological evaluation of a new series of ebselen derivatives as glutathione peroxidase (GPx) mimics and cholinesterase inhibitors against Alzheimer's disease

A series of ebselen derivatives were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and glutathione peroxidase (GPx) mimics. Most of the compounds were found to be potent against AChEs and BuChE, compounds 5e and 5i, proved to be the most potent against AChE with IC50 values of 0.76 and 0.46 μM, respectively. Among these hybrids, most of the compounds were found to be good GPx mimics compare with ebselen. The selected compounds 5e and 5i were also used to determine the catalytic parameters and in vitro hydrogen peroxide scavenging activity. The results indicate that compounds 5e and 5i may be excellent multifunctional agents for the treatment of AD.

ANION RECEPTOR, AND ELECTROLYTE USING THE SAME

Disclosed is a novel anion receptor and electrolytes containing the same. A novel anion receptor is an aromatic hydrocarbon compound having an amine substituted with electron withdrawing groups. When the anion receptor is added to the electrolyte, ionic conductivity and cation transference number of electrolytes are enhanced, thereby increasing the electrochemical stability of alkali metal batteries using the electrolytes.

Catalytic processes of oxidation by hydrogen peroxide in the presence of Br2 or HBr. Mechanism and synthetic applications

The mechanism and the synthetic applications for the oxidation of alcohols, ethers, and aldehydes by H2O2 catalyzed by Bf2 or Br- in a liquid two-phase system (aqueous and organic) are reported. Aliphatic and benzylic primary alcohols and ethers show an opposite behavior, which has been rationalized on the ground of the different electronic configurations of the intermediate alkyl (π-type) and acyl (σ-type) radicals and their influence on enthalpic and polar effects. A two-phase system is particularly useful also for an efficient benzylic bromination by Br2 or Br-; the substitution of the benzyl bromide by OH, OR, and OCOR regenerates Br-, which can be recycled. The evaluation of the relative reactivities of the involved substrates and intermediates has allowed to develop a variety of simple, facile, convenient, and selective syntheses of alcohols, aldehydes, ketones, esters, and benzyl bromides, which fulfill the conditions for practical applications.

Triazolylated teritiary amine compound or salt thereof

A triazolylated tertiary amine compound represented by general formula (I) or a salt thereof, having an aromatase inhibitory activity and being useful for preventing and treating breast cancer, mastopathy, endometriosis, prostatomergaly, etc., wherein A represents a single bond, lower alkylene or carbonyl; B represents lower alkyl, aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; D represents aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; and E represents 4H-1,2,4-triazolyl, 1H-1,2,4-triazolyl or 1H-1,2,3-triazolyl.

Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the CHRC/5 cell line.Among them the acridone derivatives were the most potent.A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain.Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone.On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy-9-oxo-N-phenyl>-4-acridinecarboxamide (84) has been selected for further development.

EFFECT OF CYCLIC ACETAL-TYPE CATIONIC SURFACTANTS ON THE BASIC DEHYDROBROMINATION REACTION

The reaction of 2-(p-nitrophenyl)ethyl bromide with hydroxide ion was studied at 50 and 25 deg C in the presence of cationic chemodegradable surfactants, i.e. trimethylammonium bromides Ia-c (alkyl: a = n-C9H19, b = n-C11H23, c = n-C13H27).The kinetic data were interpreted with the pseudo-phase ion-exchange (PIE) formalzm at both temperatures.The results indicate that the major source of rate enhancement is the increased reactant concentration in the small micellar reaction volume.The surfactant stability in micellar conditions was probed by means of a hydrolysis reaction of the surfactant 1,3-dioxolane ring.The kinetics of acid hydrolysis of Ia-c micelles, as a result of specific hydronium ion concentration, is one order of magnitude smaller than that of unaggregated systems.

Counterion Influence upon the Basic Dehydrobromination Reaction in Functional Micelles

The basic dehydrobromination reaction of 2-(p-nitrophenyl)ethyl bromide has been studied in aqueous micelles of N-hexadecyl-N,N-dimethyl-N-(2-hydroxyethyl)ammonium salts (CDHAX; X = Cl, Br, NO3) in the presence and absence of univalent salts NaX. The added salts inhibit the reaction in hydroxyfunctional micelles CDHAX, and the anion order is similar to that for reaction in micelles of nonfunctional N-hexadecyl-N,N,N-trimethylammonium ion surfactants (CTAX). The reaction kinetics only in the absence of added salts can be described quantitatively in terms of ion-exchange and acid-base equilibria and the micellar effects of the cationic micelle upon the bimolecular reaction. Key words: functional micellar catalysis, 1,2-eliminations, salts effects.

Biosynthesis of the Antibiotic Obafluorin from p-Aminophenylalanine and Glycine (Glyoxylate)

Results of experiments using 'resting' cells of Pseudomonas fluorescens with -, - and 2H2>-glycine as precursors show that glyoxylic acid is specifically the source of C-1 and C-2 of the antibiotic obafluorin 1.The 13C labelling patterns are consistent with the passage of the precursors through the tartronic semialdehyde and glyoxylate pathways.The glycine derivative 6 is not a precursor for 1.The analogues 24 and 25 of p-aminophenylalanine 3 are synthesised and tested as substrates for biosynthesis in P. fluorescens.With 24, the metabolite 26 is detected; no metabolites of 25 are detected.