4752-10-7

Basic information

• Product Name: 1,4-Dichlorophthalazine
• Synonyms: 1,4-DICHLOROPHTHALAZINE;1,4-Dichlorophtalazine;Phthalazine, 1,4-dichloro-;1,4-Dichloro-2,3-benzodiazine;Dichlorophthalazine;1,4-Dichlorophthalazine,98%
• CAS NO: 4752-10-7
• Molecular Formula: C₈H₄Cl₂N₂
• Molecular Weight: 199.04
• EINECS: 225-275-6
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridazines;PyridazinesHeterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 4752-10-7.mol
• Article Data: 42

Chemical Properties

• Melting Point: 160-162 °C(lit.)
• Boiling Point: 397.3 °C at 760 mmHg
• Flash Point: 226.4 °C
• Appearance: White to yellow/Powder or Crystalline Powder
• Density: 1.486 g/cm³
• Vapor Pressure: 3.67E-06mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: ?20°C
• Solubility: Chloroform, Methanol
• PKA: -0.44±0.30(Predicted)
• Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 1,4-Dichlorophthalazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dichlorophthalazine(4752-10-7)
• EPA Substance Registry System: 1,4-Dichlorophthalazine(4752-10-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4752-10-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4752-10-7 differently. You can refer to the following data:
1. 1,4-Dichlorophthalazine Oftens used building block in medicinal chemistry synthesis.1,2
2. 1,4-Dichlorophthalazine was used as starting reagent in the synthesis of series of 4-aryl-1-(4-methylpiperazin-1-yl)phthalazines. It was used as coupling reagent in the synthesis of novel soluble polymer-bound ligand. It was often used as building block in medicinal chemistry synthesis.

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 2708, 1965 DOI: 10.1139/v65-379

InChI:InChI=1/C8H4Cl2N2/c9-7-5-3-1-2-4-6(5)8(10)12-11-7/h1-4H

Upstream product

• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 1875-48-5 N-aminophthalamide 
• 1445-69-8 1,4-dihydroxyphthalazine 
• 10025-87-3 trichlorophosphate 
• 253-52-1 PHTHALAZINE 
• 270-75-7 isobenzofuran 
• 4397-55-1 phthalic monoacid monomethyl ester chloride 
• 4388-29-8 [2,2'-biisoindoline]-1,1',3,3'-tetraone 
• 136918-14-4 phthalimide 
• 85-44-9 phthalic anhydride 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Downstream Products

• 91-15-6 phthalonitrile 
• 113628-61-8 6-Chloro-3-p-tolyl-[1,2,4]triazolo[3,4-a]phthalazine 
• 866758-54-5 (4-tert-butylphenyl)-(4-chlorophthalazin-1-yl)amine 
• 677323-01-2 (4-chloro-phthalazin-1-yl)-p-tolyl-amine 
• 284031-04-5 (4-chlorophenyl)-(4-chlorophthalazin-1-yl)amine 
• 677323-02-3 4-chloro-N-(4-methoxyphenyl)phthalazin-1-amine 
• 677323-06-7 (4-chloro-phthalazin-1-yl)-m-tolyl-amine 
• 866758-52-3 [4-(chlorodifluoromethoxy)phenyl]-(4-chlorophthalazin-1-yl)amine 

Relevant articles and documents

Synthesis and anti-inflammatory activity evaluation of a novel series of 6-phenoxy-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide derivatives

The transcription factor nuclear factor-κB (NF-κB) controls many physiological processes including inflammation, immunity, and apoptosis. In this study, a novel series of 6-phenoxy-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide derivatives were synthesized as potent anti-inflammatory agents, which acted on tumor necrosis factor (TNF-α) as inhibitors of NF-κB activation. We showed that compounds 6h (6-(2,4-dichlorophenoxy)-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide) and 6i (6-(3-tolyloxy)-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide) showed more prominent anti-inflammatory activity than other compounds, with similar activities as the reference drug dihydrotanshinone; compound 6i showed the lowest cellular toxicity among the tested compounds. In vivo evaluation of the anti-inflammatory activity showed that compound 6i exhibited excellent anti-inflammatory activity with 58.19% inhibition at 50?mg/kg intraperitoneal (i.p.), with equal efficacy as the positive control indomethacin (100?mg/kg i.p.; 59.21% inhibition).

Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors

A new series of triazolophthalazine derivatives was designed and synthesized as topoisomerase II (Topo II) inhibitors and DNA intercalators. The synthesized derivatives were evaluated in vitro for their cytotoxic activities against three human cancer cell lines: HepG2, MCF-7, and HCT-116 cells. Compound IXb was the most potent counterpart with IC50 values of 5.39 ± 0.4, 3.81 ± 0.2, and 4.38 ± 0.3 μM, as it was about 1.47, 1.77, and 1.19 times more active than doxorubicin (IC50 = 7.94 ± 0.6, 6.75 ± 0.4, and 5.23 ± 0.3 μM) against HepG2, MCF-7, and HCT-116 cells, respectively. Additionally, the binding affinity of the synthesized compounds toward the DNA molecule was assessed using the DNA/methyl green assay. Compound?IXb showed an excellent DNA binding affinity with an IC50 value of 27.16 ± 1.2 μM, which was better than that of the reference drug doxorubicin (IC50 = 31.02 ± 1.80 μM). Moreover, compound IXb was the most potent member among the tested compounds when investigated for their Topo II inhibitory activity. Furthermore, compound IXb induced apoptosis in HepG2 cells and arrested the cell cycle at the G2/M phase. Additionally, compound IXb showed Topo II poisoning effects at 2.5 μM and Topo II catalytic inhibitory effects at 5 and 10 μM. Finally, molecular docking studies were carried out against the DNA–Topo II complex and DNA, to investigate the binding patterns of the designed compounds.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.