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

Chemical Properties

SLIGHTLY BROWN TO BEIGE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 253-52-1 differently. You can refer to the following data:
1. Phthalazine is a heterocyclic organic compound isomeric with quinoxaline, cinnoline and quinazoline. Aminophthalazine compounds serve as effective phosphodiesterase (PDE) inhibitors.
2. Phthalazine derivatives including copper and platinum complexes were induce the apoptosis in breast cancer cell lines and renal hyperemia.

Definition

ChEBI: An azaarene that is the 2,3-diaza analogue of naphthalene. The parent of the class of phthalazines.

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 
• 21452-55-1 1-cyano-1H-phthalazine-2-carboxylic acid diethylamide 
• 484-23-1 1,4-bis(hydrazino)phthalazine 
• 302-01-2 hydrazine 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 100-52-7 benzaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 576-22-7 2-Bromo-m-xylene 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 25641-99-0 α,α,α',α'-tetrachloro-o-xylene 
• 10034-85-2 hydrogen iodide 
• 13152-89-1 1,2,3,4-tetrahydrophthalazine 
• 21415-94-1 1-cyano-1H-phthalazine-2-carboxylic acid diphenylamide 

Downstream Products

• 18636-89-0 phthalazine 2-oxide 
• 17300-02-6 1,2-benzenedimethanamine 
• 65326-28-5 2-(2-oxo-2-(4-bromophenyl)ethyl)phthalazin-2-ium bromide 
• 5004-42-2 1-phenyl-1,2-dihydro-phthalazine 
• 527678-83-7 [(CuBr(P(C₆H₅)3))(phthalazine)] 
• 527678-85-9 [(CuCl(P(OC₆H₅)3))(phthalazine)] 
• 527678-84-8 [(CuI(P(C₆H₅)3))(phthalazine)] 
• 1240139-45-0 1-chloroethyl 1-phenyl-1H-phthalazine-2-carboxylate 
• 1240139-47-2 phenyl 1-vinyl-1H-phthalazine-2-carboxylate 
• 1260073-93-5 C₂₇H₂₆N₂O₅ 
• 853319-06-9 C₂₆H₂₃ClN₂O₅ 
• 853319-05-8 C₂₆H₂₃BrN₂O₅ 
• 1260073-81-1 C₂₀H₁₃N₃O₄ 

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.

Ligand Redox-Controlled Tandem Synthesis of Azines from Aromatic Alcohols and Hydrazine in Air: One-Pot Synthesis of Phthalazine

A controlled tandem synthetic route to azines from various alcohols and hydrazine hydrate by the use of a Ni(II) complex of 2,6-bis(phenylazo)pyridine as a catalyst is reported. In marked contrast to the previous report, the reaction is operative using an earth-abundant metal catalyst, milder reaction conditions, and aerobic conditions, which though are desirable but unprecedented in the literature. The catalytic reaction has a vast substrate scope including a single-step synthesis of phthalazine from 1,2-benzenedimethanol and hydrazine hydrate via intramolecular coupling. Mechanistic investigation suggests that the coordinated ligand redox controls the reaction by the use of a reversible azo (N=N)/ hydrazo (NH - NH) redox couple where the metal center is used primarily as a template.

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.