Cas no 59236-37-2 (2-Amino-4-chlorobenzaldehyde)

2-Amino-4-chlorobenzaldehyde is a versatile aromatic aldehyde with a molecular formula of C?H?ClNO. This compound features both an amino (–NH?) and a chloro (–Cl) substituent on the benzene ring, alongside a formyl (–CHO) group, making it a valuable intermediate in organic synthesis. Its reactive aldehyde group enables participation in condensation, reduction, and cyclization reactions, while the electron-donating amino and electron-withdrawing chloro groups influence its reactivity and selectivity. This compound is particularly useful in the synthesis of pharmaceuticals, agrochemicals, and heterocyclic compounds. Its well-defined structure and functional group compatibility make it a preferred choice for researchers in medicinal and industrial chemistry applications.
2-Amino-4-chlorobenzaldehyde structure
2-Amino-4-chlorobenzaldehyde structure
Product Name:2-Amino-4-chlorobenzaldehyde
CAS No:59236-37-2
MF:C7H6ClNO
MW:155.581640720367
MDL:MFCD10696881
CID:1028399
PubChem ID:11252138
Update Time:2025-08-02

2-Amino-4-chlorobenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-4-chlorobenzaldehyde
    • 2-amino-4-chloro-benzaldehyde
    • Benzaldehyde, 2-amino-4-chloro-
    • 4-chloro-2-aminobenzaldehyde
    • 2-amino-4-chlorobenz-aldehyde
    • WVXCOXXJTWKDPJ-UHFFFAOYSA-N
    • AB58432
    • AK137796
    • AB0097321
    • 59236-37-2
    • SY033923
    • DB-346741
    • O10651
    • MFCD10696881
    • SCHEMBL3208051
    • DTXSID30460077
    • DS-5897
    • A928707
    • CS-0043943
    • AKOS006303877
    • MDL: MFCD10696881
    • Inchi: 1S/C7H6ClNO/c8-6-2-1-5(4-10)7(9)3-6/h1-4H,9H2
    • InChI Key: WVXCOXXJTWKDPJ-UHFFFAOYSA-N
    • SMILES: ClC1C=CC(C=O)=C(C=1)N

Computed Properties

  • Exact Mass: 155.01388
  • Monoisotopic Mass: 155.0137915g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 129
  • 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: 2.3
  • Topological Polar Surface Area: 43.1

Experimental Properties

  • Boiling Point: 297.0±25.0℃ at 760mmHg
  • PSA: 43.09

2-Amino-4-chlorobenzaldehyde Pricemore >>

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Additional information on 2-Amino-4-chlorobenzaldehyde

Recent Advances in the Study of 2-Amino-4-chlorobenzaldehyde (CAS: 59236-37-2) and Its Applications in Chemical Biology and Pharmaceutical Research

2-Amino-4-chlorobenzaldehyde (CAS: 59236-37-2) is a key intermediate in the synthesis of various bioactive compounds and pharmaceuticals. Recent studies have highlighted its significance in drug discovery, particularly in the development of antimicrobial, anticancer, and anti-inflammatory agents. This research brief aims to provide an overview of the latest advancements related to this compound, focusing on its synthesis, biological activities, and potential applications in the pharmaceutical industry.

One of the most notable developments in the study of 2-Amino-4-chlorobenzaldehyde is its role as a precursor in the synthesis of heterocyclic compounds. Researchers have successfully utilized this compound to create novel benzimidazole and quinazoline derivatives, which exhibit promising antimicrobial properties. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that these derivatives showed significant activity against drug-resistant bacterial strains, including MRSA and Escherichia coli.

In addition to its antimicrobial potential, 2-Amino-4-chlorobenzaldehyde has been investigated for its anticancer properties. A recent study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of Schiff base complexes using this compound, which exhibited selective cytotoxicity against breast cancer cell lines (MCF-7). The study suggested that the chloro and amino functional groups play a critical role in enhancing the compound's binding affinity to cancer cell receptors.

Another area of interest is the compound's application in the development of anti-inflammatory agents. A 2022 study published in European Journal of Pharmaceutical Sciences explored the use of 2-Amino-4-chlorobenzaldehyde as a scaffold for designing COX-2 inhibitors. The resulting compounds demonstrated potent anti-inflammatory activity with reduced gastrointestinal side effects compared to traditional NSAIDs.

From a synthetic chemistry perspective, recent advancements have focused on optimizing the production of 2-Amino-4-chlorobenzaldehyde. A 2023 patent (US20230183214A1) disclosed an improved catalytic method for its synthesis, achieving higher yields and purity while reducing environmental impact. This innovation is expected to facilitate large-scale production for pharmaceutical applications.

In conclusion, 2-Amino-4-chlorobenzaldehyde (CAS: 59236-37-2) continues to be a versatile and valuable compound in chemical biology and pharmaceutical research. Its applications span antimicrobial, anticancer, and anti-inflammatory drug development, with ongoing studies exploring its full potential. Future research directions may include computational modeling to design more potent derivatives and further optimization of synthetic routes for industrial-scale production.

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