4-Nitrobenzyl bromide

Base Information

• Chemical Name: 4-Nitrobenzyl bromide
• CAS No.: 100-11-8
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.034
• Hs Code.: 2904.90
• European Community (EC) Number: 202-820-6
• NSC Number: 4609
• UNII: QCHRSPCHUE
• DSSTox Substance ID: DTXSID7049392
• Nikkaji Number: J4.977H
• Wikidata: Q26840744
• Metabolomics Workbench ID: 62444
• ChEMBL ID: CHEMBL174047
• Mol file: 100-11-8.mol

Synonyms:4-nitrobenzyl bromide;p-nitrobenzyl bromide

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Chemical Property of 4-Nitrobenzyl bromide

Chemical Property:

• Appearance/Colour: light yellow acicular crystal powder
• Vapor Pressure: 0.0016mmHg at 25°C
• Melting Point: 98 °C
• Refractive Index: 1.611
• Boiling Point: 304.2 °C at 760 mmHg
• Flash Point: 137.8 °C
• PSA: 45.82000
• Density: 1.652 g/cm³
• LogP: 3.01290
• Storage Temp.: Store at RT.
• Water Solubility.: It hydrolyzes in water. Soluble in alcohol and ether.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 214.95819
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC(=CC=C1CBr)[N+](=O)[O-]
• Description: 4-Nitrobenzyl Bromide is a C-nitro compound, appearing as a white to light yellow solid. It is soluble in alcohol and ether but hydrolyzes in water. 4-Nitrobenzyl Bromide consists of a nitrobenzene ring with a bromomethyl substituent at the para-position. 4-Nitrobenzyl Bromide falls under the category of benzyl bromides and is used as a reagent in various chemical reactions.
• Uses and Mechanism of Action: Catalytic activity for reduction of CO2: ; 4-Nitrobenzyl Bromide acts as a catalyst for the reduction of CO2, promoting the electroactivation of CO2 on modified electrode surfaces.^[1]; ; Electrosynthesis of 4-nitrophenylacetic acid: ; It serves as a substrate for the electrosynthesis of 4-nitrophenylacetic acid, which is used in the synthesis of medicines such as antitumor agents.^[1],[2]
• Production Methods: 4-Nitrobenzyl Bromide can be synthesized through various chemical reactions, including reactions involving bromomethyl substitution on nitrobenzene.
• Analysis Method: The purity and characteristics of 4-Nitrobenzyl Bromide can be analyzed using techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), mass spectrometry (MS), and nuclear magnetic resonance spectroscopy (NMR). Additionally, precautions should be taken during handling due to its reactivity and potential explosive properties.
• References: [1] The electrochemical behavior of 4-nitrobenzyl bromide and its catalytic activity for reduction of CO2 in the acetonitrile solvent at the Cu/Pd/rGO/GCE surface; DOI 10.1016/j.electacta.2020.136483; [2] Preparation and characterization of technetium and rhenium tricarbonyl complexes bearing the 4-nitrobenzyl moiety as potential bioreductive diagnostic radiopharmaceuticals. In vitro and in vivo studies; DOI 10.1016/j.ejmech.2007.05.015

Technology Process of 4-Nitrobenzyl bromide

There total 39 articles about 4-Nitrobenzyl 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: 100.0%

1-methyl-4-nitrobenzene (99-99-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Guidance literature:

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

Reference yield: 97.0%

benzyl bromide (100-39-0) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Guidance literature:

With sulfuric acid; silica gel; tetramethylammonium nitrate; for 0.0333333h;

DOI:10.1080/00397910500184685

Reference yield: 92.0%

4-nitrobenzaldehdye (555-16-8) → 1-bromomethyl-4-nitro-benzene (100-11-8)

Guidance literature:

With polymethylhydrosiloxane; dimethylbromosulphonium bromide; In chloroform; at 20 ℃; for 8h;

DOI:10.1016/j.tetlet.2007.07.125

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

2,2'-azobis(isobutyronitrile)

1-methyl-4-nitrobenzene

Downstream raw materials:

2-methyl-1-(4-nitro-benzyl)-pyridinium; bromide

4-methyl-N-(4-nitrobenzyl)pyridinium bromide

2,6-dimethyl-1-(4-nitro-benzyl)-pyridinium; bromide

3-hydroxy-1-(4-nitrobenzyl)pyridinium bromide