Phthalhydrazide

Base Information

• Chemical Name: Phthalhydrazide
• CAS No.: 1445-69-8
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 29280000
• European Community (EC) Number: 215-893-4
• NSC Number: 201511,651
• DSSTox Substance ID: DTXSID90871842
• Nikkaji Number: J80.114C
• Mol file: 1445-69-8.mol

Synonyms:2,3-DHPD;2,3-dihydro-1,4-phthalazinedione;2,3-dihydro-1,4-phthalazinedione, monoammonium salt;2,3-dihydrophthalazine-1,4-dione

Chemical Property of Phthalhydrazide

Chemical Property:

• Appearance/Colour: white powder and chunks
• Vapor Pressure: 1.41E-11mmHg at 25°C
• Melting Point: >300 ºC
• Refractive Index: 1.586
• Boiling Point: 523.5 ºC at 760 mmHg
• PKA: 10.70±0.20(Predicted)
• Flash Point: 270.4 ºC
• PSA: 65.72000
• Density: 1.336 g/cm³
• LogP: 0.21640
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in acetone and acetic acid.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

≥99.7% ^*data from raw suppliers

Phthalhydrazide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)NNC2=O
• General Description: Phthalhydrazide, also known by various synonyms such as phthalic acid cyclic hydrazide and 1,4-phthalazinediol, serves as a key reactant in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones, a class of compounds with notable biological relevance. Its role in this context involves participating in a multicomponent cyclocondensation reaction under solvent-free, InCl₃-catalyzed conditions, demonstrating its utility in green and efficient synthetic methodologies for heterocyclic frameworks.

Technology Process of Phthalhydrazide

There total 258 articles about Phthalhydrazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

phthalic anhydride (85-44-9) → 2,3-dihydrophthalazine-1,4-dione (1445-69-8)

Guidance literature:

With acetic acid; hydrazine; at 120 ℃;

DOI:10.1016/j.bmc.2018.04.048

Reference yield: 95.0%

4-<(2-Oxocyclohexyl)oxy>-1(2H)-phthalazinone (72881-42-6) → 4-hydroxy-1(2H)-phthalazinone (1445-69-8) + cyclohexanone-2-ol (533-60-8)

Guidance literature:

With sodium hydroxide; In water; for 0.5h; Heating;

DOI:10.1021/jo01295a033

Reference yield: 93.0%

N-(N3-p-toluenesulfonyl)-3-aminopropylphthalimide (38353-77-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,3-dihydrophthalazine-1,4-dione (1445-69-8) + N1-formyl-N3-tosyl-1,3-propanediamine (107976-50-1) + dimethyl amine (124-40-3)

Guidance literature:

With hydrazine hydrate; at 80 ℃; for 3h;

DOI:10.1246/cl.1986.951

upstream raw materials:

phthalic anhydride

phthalimide

benzaldehyde, hydrazone

ethanol

Downstream raw materials:

2-benzyl-2,3-dihydrophthalazine-1,4-dione

N-(p-methoxybenzylidene)aminophthalimide

4-benzoyloxy-2H-phthalazin-1-one

2-Acetyl-1.4-dioxo-1.2.3.4-tetrahydro-phthalazin

Refernces

InCl₃-catalyzed green synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones under solvent-free conditions

10.1016/j.tetlet.2013.04.109

This research aims to develop an efficient and environmentally friendly method for synthesizing 1H-pyrazolo[1,2-b] phthalazine-5,10-diones, which are significant in medicinal chemistry due to their wide range of biological activities. The study employs a one-pot, three-component cyclocondensation reaction involving phthalhydrazide, aldehydes, and malononitrile/ethyl cyanoacetate, catalyzed by InCl3 under solvent-free conditions at 80 °C. The key chemicals used include phthalhydrazide as a core reactant, various aldehydes providing different substituents, and malononitrile/ethyl cyanoacetate as the third component for the cyclocondensation. InCl3 plays a crucial role as a catalyst, enhancing the reaction rate and selectivity. The research concludes that this method offers high yields, shorter reaction times, and easy work-up procedures, making it a green and practical approach for synthesizing these heterocycles. The solvent-free condition and the use of InCl3 contribute to the environmental benignity and efficiency of the synthesis, marking a significant advancement in the green synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones.