Cas no 18268-76-3 (2-Chloro-4-hydroxy-5-methoxybenzaldehyde)

2-Chloro-4-hydroxy-5-methoxybenzaldehyde is a versatile aromatic aldehyde with a molecular formula of C8H7ClO3. It features a chloro substituent at the 2-position, a hydroxyl group at the 4-position, and a methoxy group at the 5-position, contributing to its unique reactivity and stability. This compound is widely used as a key intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its distinct substitution pattern allows for selective functionalization, making it valuable in constructing complex molecular frameworks. The presence of both electron-donating (methoxy) and electron-withdrawing (chloro) groups enhances its utility in electrophilic and nucleophilic reactions. High purity grades are available for research and industrial applications.
2-Chloro-4-hydroxy-5-methoxybenzaldehyde structure
18268-76-3 structure
Product Name:2-Chloro-4-hydroxy-5-methoxybenzaldehyde
CAS No:18268-76-3
MF:C8H7ClO3
MW:186.592381715775
MDL:MFCD02379943
CID:851334
PubChem ID:29000
Update Time:2025-07-02

2-Chloro-4-hydroxy-5-methoxybenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Chloro-4-hydroxy-5-methoxybenzaldehyde
    • 2-CHLORO-4-HYDROXY-5-METHOXY-BENZALDEHYDE
    • 2-Chlor-4-hydroxy-5-methoxy-benzaldehyd
    • 2-chloro-4-hydroxy-5-methoxybenzaldehyde(SALTDATA: FREE)
    • 6-chlorovanilin
    • 6-chlorovaniline
    • 6-Chlorovanillin
    • 6-monochlorovanillin
    • Benzaldehyde, 2-chloro-4-hydroxy-5-methoxy-
    • Vanillin, 6-chloro-
    • NSC 95796
    • HY-W077917
    • 2-Chloro-4-hydroxy-5-methoxybenzaldehyde, AldrichCPR
    • 18268-76-3
    • DB-027865
    • DTXSID7075139
    • SCHEMBL1054210
    • NSC-95796
    • BS-35793
    • J-011692
    • STK397249
    • G54997
    • Z274515356
    • MFCD02379943
    • AKOS000104246
    • NSC95796
    • UNII-2JYJ2LFP3W
    • 2JYJ2LFP3W
    • CS-0116503
    • ZOKLABLCKDZYOP-UHFFFAOYSA-N
    • EN300-332881
    • MDL: MFCD02379943
    • Inchi: 1S/C8H7ClO3/c1-12-8-2-5(4-10)6(9)3-7(8)11/h2-4,11H,1H3
    • InChI Key: ZOKLABLCKDZYOP-UHFFFAOYSA-N
    • SMILES: ClC1C=C(C(=CC=1C=O)OC)O

Computed Properties

  • Exact Mass: 186.00800
  • Monoisotopic Mass: 186.0083718g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 162
  • 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
  • XLogP3: 2.1
  • Topological Polar Surface Area: 46.5?2

Experimental Properties

  • PSA: 46.53000
  • LogP: 1.86670

2-Chloro-4-hydroxy-5-methoxybenzaldehyde Security Information

  • Hazard Category Code: 43
  • Safety Instruction: 36/37
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

2-Chloro-4-hydroxy-5-methoxybenzaldehyde 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%

2-Chloro-4-hydroxy-5-methoxybenzaldehyde Pricemore >>

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2-Chloro-4-hydroxy-5-methoxybenzaldehyde Related Literature

Additional information on 2-Chloro-4-hydroxy-5-methoxybenzaldehyde

Introduction to 2-Chloro-4-hydroxy-5-methoxybenzaldehyde (CAS No. 18268-76-3)

2-Chloro-4-hydroxy-5-methoxybenzaldehyde, identified by its Chemical Abstracts Service (CAS) number 18268-76-3, is a versatile organic compound that has garnered significant attention in the field of pharmaceutical chemistry and synthetic biology. This aromatic aldehyde features a chloro, hydroxyl, and methoxy substituent on a benzene ring, making it a valuable intermediate in the synthesis of various bioactive molecules.

The structural motif of 2-chloro-4-hydroxy-5-methoxybenzaldehyde positions it as a key precursor in the development of pharmaceutical agents, particularly those targeting neurological and inflammatory disorders. Its unique functional groups allow for diverse chemical modifications, enabling the construction of complex molecular frameworks with tailored biological activities.

In recent years, 2-chloro-4-hydroxy-5-methoxybenzaldehyde has been extensively studied for its potential in medicinal chemistry. Researchers have leveraged its reactivity to develop novel scaffolds for small-molecule drugs. For instance, studies have demonstrated its utility in generating derivatives with inhibitory effects on enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are implicated in pain and inflammation pathways.

One notable application of 2-chloro-4-hydroxy-5-methoxybenzaldehyde is in the synthesis of flavonoid-like compounds, which are known for their antioxidant and anti-inflammatory properties. The presence of both hydroxyl and methoxy groups enhances its compatibility with glycosylation and other biotransformations, facilitating the production of glycosides and other pharmacologically relevant derivatives.

Advances in computational chemistry have further highlighted the significance of 2-chloro-4-hydroxy-5-methoxybenzaldehyde as a building block. Molecular modeling studies suggest that its scaffold can be optimized to improve drug-likeness parameters, such as solubility, permeability, and metabolic stability. These insights have guided the design of next-generation therapeutic candidates targeting diseases with unmet medical needs.

The compound's role in drug discovery extends beyond simple intermediates. It has been incorporated into libraries for high-throughput screening (HTS) campaigns aimed at identifying novel bioactive molecules. Its structural features make it amenable to diversification through cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in constructing heterocyclic frameworks prevalent in modern drugs.

In the realm of natural product-inspired drug design, 2-chloro-4-hydroxy-5-methoxybenzaldehyde has served as a template for mimicking bioactive natural products. By strategically modifying its substituents, chemists have generated analogs with enhanced efficacy and reduced toxicity profiles. This approach aligns with the growing emphasis on sustainable drug development, where structural inspiration is drawn from nature but optimized through synthetic chemistry.

The compound's reactivity also makes it a valuable tool in synthetic organic chemistry education. Its transformation into more complex molecules provides students with hands-on experience in multi-step synthesis, functional group interconversion, and purification techniques. Such practical exposure is crucial for fostering the next generation of chemists capable of addressing complex synthetic challenges.

Recent patents have underscored the commercial interest in 2-chloro-4-hydroxy-5-methoxybenzaldehyde, particularly for its use in synthesizing kinase inhibitors. These inhibitors are critical targets in oncology and immunology research due to their role in modulating cell signaling pathways. The compound's ability to serve as a precursor for such high-value molecules underscores its importance in industrial-scale chemical synthesis.

The environmental impact of utilizing 2-chloro-4-hydroxy-5-methoxybenzaldehyde has also been explored. Green chemistry principles have been applied to develop more sustainable synthetic routes, minimizing waste and reducing reliance on hazardous reagents. Such efforts align with global initiatives to promote sustainable pharmaceutical manufacturing practices.

In conclusion, 2-chloro-4-hydroxy-5-methoxybenzaldehyde (CAS No. 18268-76-3) represents a cornerstone compound in modern medicinal chemistry. Its structural versatility, coupled with its utility in synthesizing bioactive molecules, positions it as an indispensable tool for researchers striving to develop innovative therapeutics. As computational methods and synthetic techniques continue to evolve, the potential applications of this compound are likely to expand further, reinforcing its significance in both academic and industrial settings.

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