2-Hydroxy-5-nitrobenzaldehyde

Base Information

• Chemical Name: 2-Hydroxy-5-nitrobenzaldehyde
• CAS No.: 97-51-8
• Deprecated CAS: 1391922-17-0,1186389-55-8
• Molecular Formula: C7H5NO4
• Molecular Weight: 167.121
• Hs Code.: 29130000
• European Community (EC) Number: 202-587-0
• NSC Number: 881
• UNII: ZJ6GGT3K66
• DSSTox Substance ID: DTXSID6059154
• Wikidata: Q72496233
• ChEMBL ID: CHEMBL3660344
• Mol file: 97-51-8.mol

Synonyms:2-hydroxy-5-nitrobenzaldehyde;5-nitrosalicylaldehyde;5-nitrosalicylaldehyde potassium

Chemical Property of 2-Hydroxy-5-nitrobenzaldehyde

Chemical Property:

• Appearance/Colour: yellow to brown crystals or powder
• Vapor Pressure: 0.000637mmHg at 25°C
• Melting Point: 125-128 °C(lit.)
• Refractive Index: 1.6280 (estimate)
• Boiling Point: 300.2 °C at 760 mmHg
• PKA: 5.08±0.22(Predicted)
• Flash Point: 137.3 °C
• PSA: 83.12000
• Density: 1.5 g/cm³
• LogP: 1.63610
• Storage Temp.: Store below +30°C.
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform, Water (Slightly)
• Water Solubility.: Soluble in water (partly).
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 167.02185764
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

5-Nitrosalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])C=O)O
• Description: 2-Hydroxy-5-nitrobenzaldehyde belongs to the category of aromatic aldehydes. It consists of a benzene ring substituted with a hydroxy group at the 2-position and a nitro group at the 5-position, with an aldehyde functional group (-CHO) attached to the benzene ring.
• Uses: 2-Hydroxy-5-nitrobenzaldehyde serves as a precursor in the synthesis of various organic compounds, including Schiff bases, molybdenum complexes, and other coordination compounds. It may have potential applications in medicine, such as being explored as a possible analeptic agent.
• Production Methods: 2-Hydroxy-5-nitrobenzaldehyde is synthesized through chemical reactions involving the condensation of appropriate precursors, such as benzaldehyde derivatives and nitro compounds.
• References: [1] Molybdenum Complexes Derived from 2-Hydroxy-5-nitrobenzaldehyde and Benzhydrazide as Potential Oxidation Catalysts and Semiconductors; DOI 10.3390/ijms25094859; [2] Spectral analysis (FT-IR, FT-Raman, UV and NMR), molecular docking, ADMET properties and computational studies: 2-Hydroxy-5-nitrobenzaldehyde; DOI 10.1016/j.jics.2023.100927; [3] Synthesis and Charaterizations of the Schiff Base Derived from 2-Hydroxy-5-Nitrobenzaldehyde Alongwith Hirshfeld Surface Analysis and Computational Study; DOI 10.1134/S0022476623050128

Technology Process of 2-Hydroxy-5-nitrobenzaldehyde

There total 36 articles about 2-Hydroxy-5-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: 96.0%

salicylaldehyde (90-02-8) → 5-Nitrosalicylaldehyde (97-51-8)

Guidance literature:

With nitric acid; acetic acid; at 20 ℃; for 6h;

DOI:10.1016/j.bmc.2014.06.041

Reference yield: 94.0%

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran) (1498-88-0) → 5-Nitrosalicylaldehyde (97-51-8)

Guidance literature:

With ozone; In methanol; at -78 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)00516-5

Reference yield: 92.0%

2-hydroxy-5-nitrobenzyl alcohol (39224-61-8) → 5-Nitrosalicylaldehyde (97-51-8)

Guidance literature:

With aluminium trichloride; 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate; In acetonitrile; for 1.5h; Heating;

upstream raw materials:

4-nitro-phenol

chloroform

2-hydroxy-5-nitrobenzyl chloride

3,6-dinitro-coumarin

Downstream raw materials:

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran)

6-nitrocoumarin

acetyloxy(2-acetyloxy-5-nitrophenyl)methyl acetate

3-acetyl-6-nitrocoumarin

Refernces

2-Hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their Zn ^II complexes: Synthesis and photophysical properties

10.1007/s11172-011-0360-z

The research focuses on the synthesis and photophysical properties of 2-hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their ZnII complexes. The purpose of this study was to extend the synthesis of fluorine-containing quinazoline derivatives and to investigate their potential as luminescent materials, given that nitrogen heterocyclic derivatives with a phenolic OH group are known as effective ligands and many complexes based on o-hydroxy azomethines exhibit luminescent properties. The researchers synthesized a series of new quinazoline derivatives and their zinc(II) complexes, examining their structures and luminescent properties. The chemicals used in this process included 2-aminobenzonitrile, salicylaldehyde, 2-hydroxy-5-nitrobenzaldehyde, 4-hydroxysalicylaldehyde, 3,5-dibromosalicylaldehyde, and various substituted hydrazines. The study concluded that the synthesized hydrazones and their ZnII complexes exhibited interesting photophysical properties, with the complexation process leading to a bathochromic shift in the absorption spectra and blue shifts in the emission peaks. The researchers also noted that the complexation considerably lowered the Stokes shift and increased the quantum yield, suggesting that these quinazoline-containing hydrazones are promising ligand systems for the design of complexes with other metals, potentially useful in electroluminescent materials and organic light-emitting diodes (OLEDs).

Synthesis, structures, and urease inhibitory activities of three copper(II) and zinc(II) complexes with 2-{[2-(2-hydroxyethylamino)ethylimino] methyl}-4-nitrophenol

10.1016/j.ejmech.2010.03.012

This research aimed to explore novel urease inhibitors by synthesizing and characterizing three new mononuclear complexes of Cu(II) and Zn(II) with the Schiff base ligand 2-{[2-(2-hydroxyethylamino)ethylimino]methyl}-4-nitrophenol (HL). The purpose was to counteract the negative effects of urease activity, which is a nickel-containing enzyme that hydrolyzes urea to produce ammonia and carbamate, leading to increased ammonia concentrations and pH elevations with implications in medicine and agriculture. The study concluded that two Cu(II) complexes, [CuLNO3] (1) and [CuClL] (2), exhibited strong urease inhibitory activities with IC50 values lower than that of acetohydroxamic acid, a standard urease inhibitor, while the Zn(II) complex [Zn(CH3COO)L] (3) showed no activity at 100 mM concentration. The chemicals used in the process included 5-nitrosalicylaldehyde, N-(2-hydroxyethyl)ethylenediamine for the synthesis of HL, and metal salts such as copper nitrate, copper chloride, and zinc acetate for the formation of the respective complexes.