253-52-1

Basic information

• Product Name: Phthalazine
• Synonyms: 2,3-Diazanaphthalene;beta-Phenodiazine;β-Phenodiazine;4,5-BENZOPYRIDAZINE;2,3-BENZODIAZINE;BENZO[D]PYRIDAZINE;PHTHALAZINE;PHZ
• CAS NO: 253-52-1
• Molecular Formula: C₈H₆N₂
• Molecular Weight: 130.15
• EINECS: 205-963-2
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyridazines
• Mol File: 253-52-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 89-92 °C(lit.)
• Boiling Point: 189 °C29 mm Hg(lit.)
• Flash Point: 178-180°C/15mm
• Appearance: Slightly brown to beige/Crystalline Powder
• Density: 1.1509 (rough estimate)
• Vapor Pressure: 0.000782mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.47(at 20℃)
• Water Solubility: Soluble in water, methanol, chloroform.
• Merck: 14,7370
• BRN: 109240
• CAS DataBase Reference: Phthalazine(CAS DataBase Reference)
• NIST Chemistry Reference: Phthalazine(253-52-1)
• EPA Substance Registry System: Phthalazine(253-52-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68
• Safety Statements: 24/25-37/39-36-26-36/37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 253-52-1(Hazardous Substances Data)

Usage

Description

Phthalazine is an azaarene that is the 2,3-diaza analogue of naphthalene, which is a heterocyclic organic compound isomeric with quinoxaline, cinnoline, and quinazoline. It is characterized as a slightly brown to beige crystalline powder.

Uses

Used in Pharmaceutical Industry:
Phthalazine is used as a chemical compound for the development of various pharmaceutical applications. Aminophthalazine compounds, derived from phthalazine, serve as effective phosphodiesterase (PDE) inhibitors, which play a crucial role in the treatment of various diseases and conditions.
Used in Anticancer Applications:
Phthalazine derivatives, including copper and platinum complexes, are used as anticancer agents, particularly in inducing apoptosis in breast cancer cell lines and renal hyperemia. These derivatives have shown potential in targeting and eliminating cancer cells, contributing to the development of novel cancer treatments.
Used in Chemical Research:
Phthalazine serves as a key component in chemical research and development, particularly in the synthesis of various organic compounds and materials. Its unique structure and properties make it a valuable building block for creating new molecules with specific functions and applications in different industries.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 2, p. 206, 1965 DOI: 10.1002/jhet.5570020219

Purification Methods

Phthalazine crystallises from diethyl ether or *benzene, and sublimes under a vacuum. The hydrochloride forms needles from EtOH with m 235-236o(dec) and the picrate has m 208-210o. [Armarego J Appl Chem 11 70 1961, Beilstein 23 H 174, 23 III/IV 1233.]

InChI:InChI=1/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H

Upstream product

• 5784-45-2 1-chlorophthalazine 
• 4752-10-7 1,4-dichlorophthalazine 
• 52866-89-4 1,1',2,2'-tetrahydro-1,1'-biphthalazine 
• 21452-55-1 1-cyano-1H-phthalazine-2-carboxylic acid diethylamide 
• 484-23-1 1,4-bis(hydrazino)phthalazine 
• 65997-87-7 (E,Z)-Benzaldehyde azine 
• 38710-51-9 2-methyl-phthalazinium; iodide 
• 5678-02-4 pyridazine-3,4-dicarboxylic acid anhydride 
• 21415-94-1 1-cyano-1H-phthalazine-2-carboxylic acid diphenylamide 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 13152-89-1 1,2,3,4-tetrahydrophthalazine 
• 10034-85-2 hydrogen iodide 
• 302-01-2 hydrazine 
• 25641-99-0 α,α,α',α'-tetrachloro-o-xylene 

Downstream Products

• 106590-18-5 5-phenyl-phthalazine 
• 97435-88-6 2-benzyl-phthalazinium; chloride 
• 59648-14-5 pyridazine-4,5-dicarboxylic acid 
• 17300-02-6 1,2-benzenedimethanamine 
• 26641-27-0 4-isopropylidene-1,1-dimethyl-1,11b-dihydro-[1,3]oxazino[4,3-a]phthalazin-2-one 
• 1624-26-6 2,3-dihydro-1H-cyclopenta[b]naphthalene 
• 78287-39-5 2-(2-chloromethylbenzoyl)-1-cyano-1,2-dihydrophthalazine 
• 106937-56-8 1,10b-Dihydro-1,1-diphenylpyrrolo<2,1-a>phthalazin-2,3-dicarbonsaeure-dimethylester 
• 128404-65-9 13-benzoylindeno<1',2':5,4>pyrrolo<2,1-a>phthalazin-12-one 
• 152897-86-4 6-<(4-Chlorophenyl)amino>-2,4-dimethyl-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione 
• 13925-27-4 1-Cyano-2-benzoyl-1,2-dihydrophthalazine 
• 65397-76-4 2-benzoyl-1-ethoxy-1,2-dihydro-phthalazine 
• 108965-28-2 Dimethyl 2-Benzoyl-1,2-dihydro-1-phthalazinylphosphonate 
• 152897-85-3 2,4-Dimethyl-6-(phenylamino)-1H,2H-phthalazino<2',1':3,4>pyrimido<4,5-d>pyrimidine-1,3(2H,4H)-dione 

Relevant articles and documents

DUAL PHOTOREACTIONS OF PHTHALAZINE FROM THE LOWEST EXCITED SINGLET AND TRIPLET STATES

Phthalazine undergoes the photoreduction and the photo-reductive dimerization simultaneously to give 1,2-dihydrophthalazine and its dimer (1H,1'H,2H,2'H-1,1'-biphthalazine), respectively, upon ultraviolet light irradiation in 2-propanol.It has been suggested that the photoreduction proceeds through the lowest excited singlet state and the photodimerization through the lowest triplet state.

Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides

A scalable and operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the same molecule through the judicious selection of a photocatalyst.

Nitrogen activation and conversion method promoted by divalent rare earth iodine compound

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for activating and converting nitrogen through a divalent rare earth compound. A divalent rare earth diodide is used as a reducing agent, a solvent is added in, the mixture reacts with nitrogen, then a hydrogen source is added in, and then the mixture reacts with an aldehyde or ketone compound to obtain an azine or pyridazine compound. According to the method, the nitrogen is activated and converted into the organic compound containing nitrogen on the mild condition. Compared with a classical ammonia synthesis path, strict reaction conditions such as high temperature, high pressure and ammonia oxidation are avoided, and the method is of great significance in developing the new technology of nitrogen molecule activation and broadening the application range of rare earth metal in organic synthesis.