4-Nitrophenethyl bromide

Base Information

• Chemical Name: 4-Nitrophenethyl bromide
• CAS No.: 5339-26-4
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.061
• Hs Code.: 29049085
• European Community (EC) Number: 226-271-7
• NSC Number: 100730,3493
• DSSTox Substance ID: DTXSID90201549
• Nikkaji Number: J104.764G
• Wikidata: Q72495122
• Mol file: 5339-26-4.mol

Synonyms:4-nitrophenethyl bromide;4-nitrophenyl-ethyl-bromide;NPB

Chemical Property of 4-Nitrophenethyl bromide

Chemical Property:

• Appearance/Colour: Slightly yellow solid.
• Vapor Pressure: 0.00115mmHg at 25°C
• Melting Point: 67-69 °C(lit.)
• Refractive Index: 1.595
• Boiling Point: 309.6 °C at 760 mmHg
• Flash Point: 141 °C
• PSA: 45.82000
• Density: 1.562g/cm³
• LogP: 3.05540
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform(Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water (partly) and methanol.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

4-Nitrophenethyl bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCBr)[N+](=O)[O-]
• General Description: 4-Nitrophenethyl bromide (also known as p-nitrophenethyl bromide) is a nitroaromatic compound that undergoes intramolecular electron transfer upon one-electron reduction, forming an anion radical. This intermediate facilitates dehalogenation, releasing bromide ions, with the reaction rate influenced by factors such as C-Br bond dissociation energy and structural features. The study highlights that substitution patterns and the spatial relationship between the nitro group and the bromoethyl moiety play a role in the efficiency of electron transfer and subsequent dehalogenation.

Technology Process of 4-Nitrophenethyl bromide

There total 11 articles about 4-Nitrophenethyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

4-ethylnitrobenzene (100-12-9,94234-68-1,34527-20-3) → (4-nitrophenyl)ethyl bromide (5339-26-4)

Guidance literature:

With dihydrogen peroxide; bromine; In dichloromethane; water; for 4h; Reflux;

Reference yield: 73.0%

4-nitrostyrene (100-13-0) → (4-nitrophenyl)ethyl bromide (5339-26-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); hydrogen bromide; In toluene; at 0 ℃; for 2h;

DOI:10.1039/c6ob00692b

Reference yield: 69.0%

2-(4-nitrophenyl)ethanol (100-27-6) → (4-nitrophenyl)ethyl bromide (5339-26-4)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In benzene; for 0.5h; Ambient temperature;

upstream raw materials:

1-phenyl-2-bromoethane

2-(4-nitrophenyl)ethanol

4-nitrobenzeneacetic acid

4-nitrophenylacetyl chloride

Downstream raw materials:

2,5-dimethyl-1-(4-nitro-phenethyl)-piperidin-4-one

N-<2-(4-nitrophenyl)ethyl>phthalimide

rac-17-(4-nitro-phenethyl)-morphinane

methyl-(4-nitro-phenethyl)-sulfone

Refernces

INTRAMOLECULAR ELECTRON TRANSFER AND DEHALOGENATION OF NITROAROMATIC ANION RADICALS.

10.1021/ja00341a003

The study investigates the intramolecular electron transfer and dehalogenation processes in a series of nitroaromatic compounds containing halogens (Cl, Br) or tosyl groups at various positions. These compounds undergo one-electron reduction to form anion radicals, which then transfer an electron intramolecularly and release halide or tosylate ions. The rates of dehalogenation are influenced by factors such as the C-X bond dissociation energies, the size and nature of the bridging group, and the relative positions of these groups. The study demonstrates that a-substitution with methyl or chlorine groups increases the rate of dehalogenation by stabilizing the resulting radical and decreasing the C-X bond dissociation energy. Additionally, the study explores the effect of the distance between the halogen and the aromatic ring, as well as the importance of direct electron transfer through space rather than through the aromatic p system. The compounds synthesized and studied include p-nitrobenzyl halides, p-nitrobenzyl tosylate, p-nitrophenylethyl bromide, p-nitrophenylvinyl and -allyl bromides, and nitronaphthalenes with various substituents. The results provide insights into the mechanisms of intramolecular electron transfer and dehalogenation in these systems.