Cas no 80410-57-7 (3-Methoxy-4-nitrobenzaldehyde)

3-Methoxy-4-nitrobenzaldehyde is a nitro-substituted aromatic aldehyde with the molecular formula C?H?NO?. This compound features a methoxy group at the 3-position and a nitro group at the 4-position relative to the aldehyde functionality, making it a versatile intermediate in organic synthesis. Its electron-withdrawing nitro group enhances reactivity in nucleophilic aromatic substitution reactions, while the aldehyde group serves as a key functional group for further derivatization. The compound is commonly employed in the synthesis of pharmaceuticals, agrochemicals, and dyes due to its well-defined reactivity profile. It exhibits stability under standard conditions and is compatible with a range of synthetic methodologies, offering utility in multi-step synthetic routes.
3-Methoxy-4-nitrobenzaldehyde structure
3-Methoxy-4-nitrobenzaldehyde structure
Product Name:3-Methoxy-4-nitrobenzaldehyde
CAS No:80410-57-7
MF:C8H7NO4
MW:181.145482301712
MDL:MFCD08703367
CID:707683
PubChem ID:11492043
Update Time:2025-05-21

3-Methoxy-4-nitrobenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3-Methoxy-4-nitrobenzaldehyde
    • Benzaldehyde,3-methoxy-4-nitro-
    • 3-methoxy-4-nitro-benzaldehyde
    • Benzaldehyde,3-methoxy-4-nitro
    • WUTIWOZYHHSBBU-UHFFFAOYSA-N
    • 2531AC
    • NE48274
    • 3-Methoxy-4-nitrobenzaldehyde (ACI)
    • DS-13771
    • DTXSID90467486
    • SCHEMBL1159451
    • O11030
    • AKOS011395915
    • A916088
    • EN300-124541
    • CS-0069818
    • NICOTINOYLAZIDE
    • MFCD08703367
    • Z959304258
    • 80410-57-7
    • MDL: MFCD08703367
    • Inchi: 1S/C8H7NO4/c1-13-8-4-6(5-10)2-3-7(8)9(11)12/h2-5H,1H3
    • InChI Key: WUTIWOZYHHSBBU-UHFFFAOYSA-N
    • SMILES: O=CC1C=C(OC)C([N+](=O)[O-])=CC=1

Computed Properties

  • Exact Mass: 181.03800
  • Monoisotopic Mass: 181.03750770g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 201
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 1.4
  • Topological Polar Surface Area: 72.1

Experimental Properties

  • Density: 1.322
  • Boiling Point: 334.8 ℃/760mmHg
  • Flash Point: 171 °C
  • PSA: 72.12000
  • LogP: 1.93910

3-Methoxy-4-nitrobenzaldehyde Security Information

3-Methoxy-4-nitrobenzaldehyde Customs Data

  • HS CODE:2913000090
  • Customs Data:

    China Customs Code:

    2913000090

    Overview:

    2913000090 Item2912Other derivatives of the listed products [refer to halogenation,sulfonation,Nitrosative or nitrosative derivatives]. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:5.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    HS: 2913000090 halogenated, sulphonated, nitrated or nitrosated derivatives of products of heading 2912 Educational tariff:17.0% Tax rebate rate:9.0% Regulatory conditions:none Most favored nation tariff:5.5% General tariff:30.0%

3-Methoxy-4-nitrobenzaldehyde Pricemore >>

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3-Methoxy-4-nitrobenzaldehyde Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Nitric acid ;  -10 °C; 1 h, -10 °C; -10 °C → rt; 1 h, rt
Reference
Dicyanovinyl-substituted J147 analogue inhibits oligomerization and fibrillation of β-amyloid peptides and protects neuronal cells from β-amyloid-induced cytotoxicity
Kim, Kyoungdo; et al, Organic & Biomolecular Chemistry, 2015, 13(37), 9564-9569

Production Method 2

Reaction Conditions
1.1 Reagents: Nitric acid Solvents: Acetic acid ,  Water ;  3 h, rt → 0 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  5 h, 0 °C
Reference
Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells
Chen, Bifeng; et al, Organic & Biomolecular Chemistry, 2014, 12(30), 5629-5633

Production Method 3

Reaction Conditions
1.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane
Reference
Synthesis and biological evaluation of aryl azide derivatives of combretastatin A-4 as molecular probes for tubulin
Pinney, K. G.; et al, Bioorganic & Medicinal Chemistry, 2000, 8(10), 2417-2425

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; overnight, rt
Reference
Discovery of a Tetrahydrobenzisoxazole Series of γ-Secretase Modulators
Zhao, Zhiqiang ; et al, ACS Medicinal Chemistry Letters, 2017, 8(10), 1002-1006

Production Method 5

Reaction Conditions
1.1 Reagents: Oxygen Solvents: Dimethyl sulfoxide ;  24 h
Reference
Catalyst/Additive Free Oxidation of Benzyl Bromides to Benzaldehydes
Aman, Hasil ; et al, ChemistrySelect, 2020, 5(47), 15015-15019

Production Method 6

Reaction Conditions
Reference
Imidazol-5-one as an Acceptor in Donor-Acceptor Cyclopropanes: Cycloaddition with Aldehydes
Mikhaylov, Andrey A. ; et al, Organic Letters, 2020, 22(7), 2740-2745

Production Method 7

Reaction Conditions
Reference
Arenecarbaldehydes: synthesis by reduction
Ditrich, K., Science of Synthesis, 2007, 25, 563-574

Production Method 8

Reaction Conditions
1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  rt; 3 h, 60 °C
2.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  16 h, rt
Reference
Affinity-Driven Covalent Modulator of the Glyceraldehyde-3-Phosphate Dehydrogenase (GAPDH) Cascade
Chern, Jeffy ; et al, Angewandte Chemie, 2018, 57(24), 7040-7045

3-Methoxy-4-nitrobenzaldehyde Raw materials

3-Methoxy-4-nitrobenzaldehyde Preparation Products

3-Methoxy-4-nitrobenzaldehyde Related Literature

Additional information on 3-Methoxy-4-nitrobenzaldehyde

Comprehensive Overview of 3-Methoxy-4-nitrobenzaldehyde (CAS No. 80410-57-7): Properties, Applications, and Industry Insights

3-Methoxy-4-nitrobenzaldehyde (CAS No. 80410-57-7) is a versatile organic compound widely used in pharmaceutical, agrochemical, and specialty chemical industries. This nitro-substituted benzaldehyde derivative features a methoxy group at the 3-position and a nitro group at the 4-position, imparting unique reactivity for heterocyclic synthesis and intermediate applications. Its molecular formula (C8H7NO4) and molar mass (181.15 g/mol) make it a critical building block for fine chemical manufacturing.

The compound's yellow crystalline powder form exhibits a melting point range of 98-102°C, with solubility in polar organic solvents like ethanol and dimethyl sulfoxide (DMSO). Researchers value its electron-withdrawing nitro group for facilitating nucleophilic aromatic substitution reactions, while the methoxy group enhances solubility and directs subsequent functionalization. Recent studies highlight its role in developing non-linear optical materials and pharmaceutical intermediates, aligning with growing interest in sustainable synthesis methods.

In pharmaceutical applications, 3-Methoxy-4-nitrobenzaldehyde serves as a precursor for antimicrobial agents and central nervous system (CNS) drugs. The compound's structural features enable the construction of benzimidazole derivatives with potential biological activity. Industry reports indicate rising demand for this intermediate in generic drug production, particularly for medications targeting metabolic disorders. Its use in catalyzed cross-coupling reactions has gained attention in green chemistry initiatives, addressing environmental concerns in chemical manufacturing.

The agrochemical sector utilizes 80410-57-7 for synthesizing herbicide intermediates and plant growth regulators. The nitro group's reactivity allows for efficient transformation into amino derivatives, which are crucial for developing crop protection agents. Recent patent literature reveals innovative applications in controlled-release formulations, responding to the agricultural industry's need for precision delivery systems. Analytical studies demonstrate the compound's stability under standard storage conditions (room temperature, protected from light), making it suitable for global supply chains.

From a technical perspective, 3-Methoxy-4-nitrobenzaldehyde exhibits characteristic FT-IR absorption bands at 1685 cm-1 (C=O stretch) and 1520 cm-1 (NO2 asymmetric stretch), with H-NMR signals at δ 10.4 ppm (aldehyde proton) and δ 7.5-8.1 ppm (aromatic protons). Quality control specifications typically require ≥98% purity by HPLC analysis, with strict limits on heavy metal content for pharmaceutical-grade material. Modern process optimization techniques have improved synthetic yields through microwave-assisted reactions and continuous flow chemistry approaches.

Market analysis shows increasing interest in 80410-57-7 from emerging economies developing their pharmaceutical API industries. Regulatory compliance remains crucial, with manufacturers providing REACH registration dossiers and GMP certification documentation. The compound's structure-activity relationship continues to inspire research into multi-target drug design, particularly in neurodegenerative disease research. Environmental fate studies confirm its biodegradability under aerobic conditions, supporting its use in eco-friendly chemical processes.

Recent scientific literature highlights novel applications of 3-Methoxy-4-nitrobenzaldehyde in material science, including its use as a monomer for conducting polymers and coordination complexes with transition metals. The compound's electron-deficient aromatic system makes it valuable for developing organic semiconductors and photovoltaic materials. These applications align with global trends toward renewable energy technologies and smart materials development.

Quality assurance protocols for CAS 80410-57-7 emphasize spectroscopic characterization (including UV-Vis and mass spectrometry) alongside traditional wet chemistry methods. The compound's structure-property relationships are frequently studied using computational chemistry tools, particularly density functional theory (DFT) calculations predicting its behavior in catalytic systems. These advanced analytical approaches support the compound's expanding role in high-value chemical production.

Supply chain professionals note stable availability of 3-Methoxy-4-nitrobenzaldehyde from major chemical producers, with technical and pharmaceutical grades meeting diverse industry requirements. Current research explores bio-catalytic production methods using engineered enzymes, reflecting the chemical industry's shift toward biotechnology solutions. The compound's regioselective reactivity continues to make it valuable for complex molecule assembly in both academic and industrial settings.

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