67073-39-6

Basic information

• Product Name: 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE
• Synonyms: 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE;TIMTEC-BB SBB003688;4-Chloro-5-nitro-o-phenylenediamine,98%;4-Chloro-5-nitrobenzene-1,2-diamine
• CAS NO: 67073-39-6
• Molecular Formula: C₆H₆ClN₃O₂
• Molecular Weight: 187.58
• Mol File: 67073-39-6.mol

Chemical Properties

• Melting Point: 189-193 °C
• Boiling Point: 458.9°Cat760mmHg
• Flash Point: 231.3°C
• Appearance: Red/Crystalline Powder
• Density: 1.592g/cm³
• Vapor Pressure: 1.32E-08mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.46±0.10(Predicted)
• CAS DataBase Reference: 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE(67073-39-6)
• EPA Substance Registry System: 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE(67073-39-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 2811
• Hazardous Substances Data: 67073-39-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE is used as a key intermediate compound for the synthesis of purinone compounds, which serve as DNA-PK inhibitors. These inhibitors play a crucial role in the treatment of cancer by targeting the DNA-dependent protein kinase, a critical enzyme involved in the repair of DNA double-strand breaks. By inhibiting this enzyme, the compound can potentially enhance the effectiveness of cancer therapies and improve patient outcomes.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, 4-CHLORO-5-NITRO-O-PHENYLENEDIAMINE can also be utilized as a building block in the synthesis of various other organic compounds. Its unique structural features, including the chlorine and nitro substituents, make it a versatile starting material for the development of new molecules with potential applications in different industries, such as agrochemicals, dyes, and materials science.

InChI:InChI=1/C6H6ClN3O2/c7-3-1-4(8)5(9)2-6(3)10(11)12/h1-2H,8-9H2

Upstream product

• 113269-04-8 N-[4-chloro-5-nitro-2-(4-toluenesulfonylamino)-phenyl]-4-toluenesulfonamide 
• 541-73-1 1,3-Dichlorobenzene 
• 100245-74-7 1-azido-5-chloro-2,4-dinitro-benzene 
• 3698-83-7 2,4-dichloro-1,5-dinitrobenzene 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 27185-54-2 N,N'-(4-chloro-1,2-phenylene)bis(4-methylbenzenesulfonamide) 
• 98138-02-4 1-chloro-2-nitro-4,5-dinitroso-benzene 

Downstream Products

• 122457-29-8 3,7-dimethyl-6-aminoquinoxaline 
• 916051-69-9 1,1-dimethylethyl 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-chloro-6-nitro-1H-benzimidazole-1-carboxylate 
• 1383677-25-5 (7-(2-(methylsulfonyl)phenyl)quinoxalin-6-yl)methanamine 
• 1383677-24-4 6-(azidomethyl)-7-(2-(methylsulfonyl)phenyl)quinoxaline 
• 1383677-23-3 6-(bromomethyl)-7-(2-(methylsulfonyl)phenyl)quinoxaline 
• 1383677-21-1 6-methyl-7-(2-(methylsulfonyl)phenyl)quinoxaline 
• 1383677-07-3 4-amino-6-((7-(2-(methylsulfonyl)phenyl)-quinoxalin-6-yl)methylamino)pyrimidine-5-carbonitrile 
• 60713-78-2 5-chloro-6-nitro-1H-benzo[]imidazol-2(3H)-one 
• 109541-21-1 6-chloro-7-nitroquinoxaline 

Relevant articles and documents

THE FOUR 6-HALO-7-NITROQUINOXALINES

The study of relative nucleofugicities of nitro and halogen in quinoxalines required the synthesis of the four 6-halo-7-nitroquinoxalines 2a-d.The fluoro-, chloro- and bromo-derivatives were made from the commercially available or readily accessible 1,2-diamino-4-halobenzenes, using the nitration of the corresponding p-toluenesulfonamides.This scheme failed in the case of the iodo compound because of extensive nitro-deiodination.The synthesis of 6-iodo-7-nitroquinoxaline was finally achieved from m-fluoroiodobenzene by taking advantage of the high reactivity of fluorine, compared to iodine, in 2,4-dinitrohalobenzenes.

Process for the manufacture of benzimidazolones-(2)

Process for the manufacture of benzimidazolones-(2) wherein an o-phenylenediamine is reacted with optionally alkylated urea in the ratio of 1 to 1.3 moles per mole o-phenylenediamine in an organic solvent which has a solubility in water of not more than 5 g/l and has a boiling point above 100° C, at a temperature between 100° and 200° C.