57835-96-8

Basic information

• Product Name: 6-Chlorophthalazinone
• Synonyms: 6-Chlorophthalazinone;6-chlorophthalazin-1-ol;6-chloro-1,2-dihydrophthalazin-1-one;1(2H)-PHTHALAZINONE, 6-CHLORO-
• CAS NO: 57835-96-8
• Molecular Formula: C₈H₅ClN₂O
• Molecular Weight: 181
• Mol File: 57835-96-8.mol

Chemical Properties

• Melting Point: 272.2-273.5 °C
• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• PKA: 11.66±0.20(Predicted)
• CAS DataBase Reference: 6-Chlorophthalazinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chlorophthalazinone(57835-96-8)
• EPA Substance Registry System: 6-Chlorophthalazinone(57835-96-8)

Safety Data

• Hazardous Substances Data: 57835-96-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Chlorophthalazinone is used as a key intermediate in the synthesis of phthalazine compounds. These compounds act as p38 MAP kinase modulators, which are essential in the treatment and prophylaxis of protein kinase-mediated diseases. By targeting the p38 MAP kinase pathway, these compounds can potentially regulate cellular responses and provide therapeutic benefits in various conditions.
Used in Research and Development:
In addition to its pharmaceutical applications, 6-Chlorophthalazinone is also utilized in research and development for the discovery and design of novel p38 MAP kinase inhibitors. These inhibitors can be further optimized and developed into more effective drugs for the treatment of protein kinase-mediated diseases, such as inflammatory disorders, autoimmune diseases, and certain types of cancer.

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Relevant articles and documents

Regioselective Functionalization of Chlorophthalazine Derivatives

Chlorophthalazines were efficiently metalated using tmpZnClLiCl under microwave irradiation. This provided novel substituted phthalazine derivatives after subsequent trapping of the resulting organometallic reagents with various electrophiles. Moreover, Negishi cross-coupling reactions have been performed affording new polyfunctionalized phthalazine scaffolds in very good yields.

Practical synthesis of a p38 MAP kinase inhibitor

p38 MAP kinase inhibitors have attracted considerable interest as potential agents for the treatment of inflammatory diseases. Herein, we describe a concise and efficient synthesis of inhibitor 1 that is based on a phthalazine scaffold. Highlights of our approach include a practical synthesis of a 1,6-disubstituted phthalazine building block 24 as well as the one-pot formation of boronic acid 27. Significant synthetic work to understand the reactivity principles of the intermediates helped in selection of the final synthetic route. Subsequent optimization of the individual steps of the final sequence led to a practical synthesisof 1.

Development of a practical synthesis of a p38 MAP kinase inhibitor

A practical synthesis of the phthalazine-based p38 MAP kinase inhibitor [(S)-2] was needed for an ongoing program. Vibrational circular dichroism provided the assignment of the absolute stereochemistry of the target compound. The selected synthetic route

Phthalazine, aza- and diaza-phthalazine compounds and methods of use

The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation and related conditions. The compounds have a general Formula I wherein A1, A2, B, R1, R2, R3 and R4 are defined herein. The invention also comprises pharmaceutical compositions including one or more compounds of Formula I, uses of such compounds and compositions for treatment of kinase mediated diseases including rheumatoid arthritis, psoriasis and other inflammation disorders, as well as intermediates and processes useful for the preparation of compounds of Formula I.

Process for producing phthalazinone and derivatives of the same

1-PHTHALAZINONE AND 1-PHTHALAZINONE DERIVATIVES OF THE FOLLOWING FORMULA: STR1 wherein R1 represents a hydrogen atom, an alkyl group, an aralkyl group, an acyloxyl group, an alkoxyl group, a halogen atom, a nitro group, an amino group or an amido group; and R2 represents a hydrogen atom, an alkyl group or an aryl group. Such can be prepared at good yields by the reaction of a benzoic acid derivative of the following formula: STR2 wherein R1 has the same meanings as defined above; X represents a halogen atom; and Y represents a hydroxyl group, an alkoxyl group or a halogen atom; with hydrazine or a hydrazine derivative of the following formula: wherein R2 has the same meanings as defined above.