3-Nitrobenzaldehyde

Base Information

• Chemical Name: 3-Nitrobenzaldehyde
• CAS No.: 99-61-6
• Molecular Formula: C7H5NO3
• Molecular Weight: 151.122
• Hs Code.: 2913.00
• European Community (EC) Number: 202-772-6
• NSC Number: 5504
• UNII: G4O92KO71Z
• DSSTox Substance ID: DTXSID8049383
• Nikkaji Number: J43.345D
• Wikipedia: 3-Nitrobenzaldehyde
• Wikidata: Q2816007
• ChEMBL ID: CHEMBL238132
• Mol file: 99-61-6.mol

Synonyms:3-nitrobenzaldehyde;meta-nitrobenzaldehyde

Chemical Property of 3-Nitrobenzaldehyde

Chemical Property:

• Appearance/Colour: yellowish to yellow-brown granular powder
• Vapor Pressure: 0.00966mmHg at 25°C
• Melting Point: 56 °C
• Refractive Index: 1.617
• Boiling Point: 264.5 °C at 760 mmHg
• Flash Point: 128.6 °C
• PSA: 62.89000
• Density: 1.338 g/cm³
• LogP: 1.93050
• Storage Temp.: ?20°C
• Sensitive.: Air Sensitive
• Solubility.: 1.6g/l
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.026943022
• Heavy Atom Count: 11
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

3-Nitrobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-51/53-22
• Safety Statements: 26-36-24/25-61-37/39-29

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])C=O
• Description: 3-Nitrobenzaldehyde, meta-nitrobenzaldehyde or m-nitrobenzaldehyde is an organic aromatic compound containing a nitro group meta-substituted to an aldehyde. 3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid.
• Uses: 3-Nitrobenzaldehyde is a benzaldhyde with a nitro group in the meta position. 3-Nitrobenzaldehyde is used in the synthesis of other organic compounds, ranging from pharmaceuticals to plastic additives and intermediate for the processing of perfume and flavoring compounds and in the preparation of certain aniline dyes.

Technology Process of 3-Nitrobenzaldehyde

There total 221 articles about 3-Nitrobenzaldehyde 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: 93.0%

3,6,6-Trimethyl-4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester (117227-33-5) → 3-nitro-benzaldehyde (99-61-6) + 3-nitrobenzonitrile (619-24-9)

Guidance literature:

With sodium methylate; In ethanol; for 3h; Product distribution; Heating;

Reference yield: 79.0%

1-nitro-3-vinyl-benzene (586-39-0,51209-60-0) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-nitro-benzaldehyde (99-61-6)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1007/s10562-011-0668-1

Reference yield: 56.0%

3-Methyl-4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid diethyl ester (117227-24-4) → 3-nitro-benzaldehyde (99-61-6) + 3-Methyl-4H-cyclopenta-1,2,4-triazin-5,7-dicarbonsaeure-diethylester (117227-45-9) + 3-nitrobenzonitrile (619-24-9)

Guidance literature:

With ethanol; Heating;

upstream raw materials:

3-nitrobenzaldehyde-4-nitrophenylhydrazone

1-[bis(ethylthio)methyl]-3-nitrobenzene

1-methyl-3-nitrobenzene

3-Nitrobenzyl alcohol

Downstream raw materials:

acetaldehyde

3-nitrobenzonitrile

2,6-bis-(3-nitro-trans-styryl)-pyridine

(3-nitro-benzylidene)-pyridin-3-yl-amine

Refernces

Cobalt(II) and copper(II) complexes of 1-nitrobenzyl-2-nitrophenylbenzimidazole: Synthesis, characterization and antibacterial activity studies

10.1080/00945719608004342

The research details the synthesis, characterization, and antibacterial activity studies of cobalt(II) and copper(II) complexes with the ligand 1-nitrobenzyl-2-nitrophenylbenzimidazole (NBPBI). The purpose of the study was to explore the potential antibacterial properties of these metal-organic complexes, which were characterized using various physico-chemical techniques including elemental analysis, conductance, magnetic susceptibility measurements, UV-visible, near-IR, IR, cyclic voltammetry, EPR, and thermal studies. The conclusions drawn from the research indicated that the complexes exhibited antibacterial activity against both gram-negative and gram-positive bacteria, with varying degrees of effectiveness. The chemicals used in the synthesis process included cobalt(II) and copper(II) halides, m-nitrobenzaldehyde, o-phenylenediamine, and other reagents of Analar grade purity, with solvents purified by standard procedures. The complexes were found to be non-electrolytes in acetone, and their structures suggested a tetrahedral geometry for cobalt(II) complexes and a square planar geometry for copper(II) complexes. The end products of thermal decomposition were metal oxides.

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

10.1039/c0ob00644k

The study presents an efficient one-pot synthesis method for highly functional alkenes through a phosphine-catalyzed tandem three-component reaction involving aldehydes, alkyl vinyl ketones, and amides. The process utilizes either EtPPh2 or PPh3 as catalysts and achieves high yields (68–99%) with excellent stereoselectivity (E/Z ratios up to 98:2) within a total reaction time of 3 to 29.5 hours. The study also explores the scope of the reaction with various aryl- and heteroaryl-substituted aldehydes, amides, and alkyl vinyl ketones, demonstrating the versatility and practicality of the method. The reaction mechanism is proposed to involve a Morita–Baylis–Hillman reaction followed by a Michael addition, leading to the formation of the desired alkenes. The mild reaction conditions and the high atom economy of the process make it a valuable addition to organic synthesis.