Cas no 89891-87-2 (Phthalazine, 1-chloro-7-nitro-)

1-Chloro-7-nitrophthalazine is a heterocyclic aromatic compound featuring a phthalazine core substituted with a chlorine atom at the 1-position and a nitro group at the 7-position. This compound is of interest in synthetic organic chemistry due to its utility as a versatile intermediate in the preparation of more complex heterocyclic systems, pharmaceuticals, and agrochemicals. The presence of both electron-withdrawing groups (chloro and nitro) enhances its reactivity in nucleophilic substitution and coupling reactions, making it valuable for constructing nitrogen-containing scaffolds. Its well-defined structure and functional group compatibility enable precise modifications, supporting applications in medicinal chemistry and materials science research.
Phthalazine, 1-chloro-7-nitro- structure
89891-87-2 structure
Product Name:Phthalazine, 1-chloro-7-nitro-
CAS No:89891-87-2
MF:C8H4ClN3O2
MW:209.589260101318
CID:4936472
Update Time:2025-06-08

Phthalazine, 1-chloro-7-nitro- Chemical and Physical Properties

Names and Identifiers

    • 1-Chloro-7-nitrophthalazine
    • Phthalazine, 1-chloro-7-nitro-
    • Inchi: 1S/C8H4ClN3O2/c9-8-7-3-6(12(13)14)2-1-5(7)4-10-11-8/h1-4H
    • InChI Key: DKRVAOKHJVRWKL-UHFFFAOYSA-N
    • SMILES: ClC1=C2C=C(C=CC2=CN=N1)[N+](=O)[O-]

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 0
  • Complexity: 233
  • XLogP3: 1.9
  • Topological Polar Surface Area: 71.6

Phthalazine, 1-chloro-7-nitro- Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
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$938.00 2023-08-31
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
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1-Chloro-7-nitrophthalazine
89891-87-2 98%
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Additional information on Phthalazine, 1-chloro-7-nitro-

Phthalazine, 1-chloro-7-nitro- (CAS No. 89891-87-2): A Comprehensive Overview

Phthalazine, 1-chloro-7-nitro- (CAS No. 89891-87-2) is a significant compound in the field of pharmaceutical chemistry, exhibiting a unique structural framework that has garnered considerable attention from researchers worldwide. This heterocyclic aromatic compound, characterized by its nitro and chloro substituents, possesses intriguing chemical properties that make it a valuable intermediate in the synthesis of various pharmacologically active molecules.

The structure of Phthalazine, 1-chloro-7-nitro-, consists of a fused benzene and pyridazine ring system, with the presence of a chlorine atom at the 1-position and a nitro group at the 7-position. This specific arrangement imparts distinct reactivity patterns, making it a versatile building block for medicinal chemists. The nitro group is particularly noteworthy, as it can undergo reduction to form an amine or serve as a leaving group in nucleophilic substitution reactions, thereby facilitating the construction of more complex molecular architectures.

In recent years, Phthalazine derivatives have been extensively studied for their potential applications in drug discovery. The 1-chloro-7-nitro substitution pattern enhances the electrophilicity of the molecule, allowing for further functionalization and derivatization. This property has been exploited in the development of novel therapeutic agents targeting various diseases, including cancer and infectious disorders.

One of the most compelling aspects of Phthalazine, 1-chloro-7-nitro-, is its role as a precursor in the synthesis of anticancer agents. Researchers have demonstrated that modifications to this core scaffold can lead to compounds with potent cytotoxic effects against multiple cancer cell lines. For instance, studies have shown that certain phthalazine derivatives exhibit inhibitory activity against kinases and other enzymes overexpressed in tumor cells, suggesting their potential as inhibitors of tumor growth and progression.

The pharmacological activity of Phthalazine, 1-chloro-7-nitro-, is further enhanced by its ability to interact with biological targets such as DNA and proteins. The nitro group can participate in redox reactions, generating reactive species that induce cellular stress and apoptosis in cancer cells. Additionally, the chlorine atom provides a handle for further chemical manipulation, enabling the development of prodrugs or targeted delivery systems that enhance bioavailability and therapeutic efficacy.

Recent advances in computational chemistry have also contributed to a deeper understanding of the mechanisms underlying the biological activity of Phthalazine derivatives. Molecular modeling studies have revealed insights into how these compounds bind to their targets and how structural modifications can fine-tune their pharmacological properties. These findings have guided the design of next-generation drugs with improved selectivity and reduced side effects.

The synthesis of Phthalazine, 1-chloro-7-nitro-, involves multi-step organic transformations that highlight its synthetic utility. Common synthetic routes include chlorination and nitration of phthalazine precursors, followed by purification steps to isolate the desired product. Advances in synthetic methodologies have enabled higher yields and purities, making it more feasible to explore its applications in drug development.

Moreover, Phthalazine derivatives have shown promise in addressing infectious diseases. The structural features of these compounds allow them to disrupt essential processes in pathogens such as bacteria and viruses. For example, some phthalazine-based molecules have demonstrated activity against multidrug-resistant bacterial strains by interfering with bacterial cell wall synthesis or DNA replication.

The drug discovery pipeline continues to benefit from the versatility of Phthalazine, 1-chloro-7-nitro-. Researchers are exploring novel derivatives with enhanced binding affinity and improved pharmacokinetic profiles through structure-activity relationship (SAR) studies. These efforts are complemented by collaborations between academic institutions and pharmaceutical companies aimed at translating laboratory findings into clinical candidates.

In conclusion, Phthalazine, 1-chloro-7-nitro-, represents a fascinating compound with significant potential in pharmaceutical research. Its unique structural features and reactivity patterns make it an invaluable tool for synthesizing novel therapeutic agents targeting various diseases. As our understanding of its biological activity continues to grow, so too does its importance in advancing drug discovery efforts worldwide.

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