4693-02-1

Basic information

• Product Name: 5-NITROISATOIC ANHYDRIDE
• Synonyms: 5-NITROISATOIC ANHYDRIDE;6-NITRO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;4(1h)-dione,6-nitro-2h-1-benzoxazine-2;6-Nitro IA;6-Nitro-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione;6-Nitro-1,4-dihydro-2H-3,1-benzoxazine-2,4-dione;6-Nitroisatoic anhydride;6-nitro-1H-3,1-benzoxazine-2,4-dione
• CAS NO: 4693-02-1
• Molecular Formula: C₈H₄N₂O₅
• Molecular Weight: 208.13
• EINECS: 225-151-1
• Product Categories: pharmacetical
• Mol File: 4693-02-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 259 °C
• Boiling Point: 347.31°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.623±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.29±0.20(Predicted)
• CAS DataBase Reference: 5-NITROISATOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROISATOIC ANHYDRIDE(4693-02-1)
• EPA Substance Registry System: 5-NITROISATOIC ANHYDRIDE(4693-02-1)

Safety Data

• Hazardous Substances Data: 4693-02-1(Hazardous Substances Data)

Usage

Preparation

5-Nitroisatoic anhydride is prepared from 5-nitro indole (9g) by stirring in a 4:1 mixture of CH3CN/H2O for 1 h at 40℃. 1 H NMR (DMSO-d6): δ12.34 (s, Br., 1H), 8.59 (s Hz, 1H), 8.51 (d, J = 7.8 Hz, 1H), 7.31 (d, J = 8.7 Hz, 1H).

InChI:InChI=1/C8H4N2O5/c11-7-5-3-4(10(13)14)1-2-6(5)9-8(12)15-7/h1-3H,(H,9,12)

Upstream product

• 118-48-9 isatoic anhydride 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 1066-30-4 chromium(lll) acetate 
• 611-09-6 5-nitroisatin 
• 6146-52-7 5-nitroindole 
• 75-44-5 phosgene 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 201230-82-2 carbon monoxide 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 124-38-9 carbon dioxide 
• 1339630-41-9 C₁₂H₁₄N₂O₆ 
• 610-27-5 4-nitrophthalic acid 
• 5466-84-2 4-nitrophthalic anhydride 

Downstream Products

• 99358-81-3 1-(2-amino-5-nitro-benzoyl)-aziridine 
• 100128-01-6 1-(2-amino-5-nitro-benzoyl)-2,2-dimethyl-aziridine 
• 87597-83-9 2-amino-4-hydroxy-6-nitroquinazoline 
• 87723-26-0 6-Nitro-1-(3,4,5-trimethoxy-benzoyl)-1H-benzo[d][1,3]oxazine-2,4-dione 
• 123333-36-8 2-Amino-5-nitro-N-p-tolyl-benzamide 
• 6943-17-5 6-nitroquinazolin-4-ol 
• 144129-05-5 7-Nitro-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 
• 90971-98-5 5-Nitroanthranilsaeure-N²,N²-dimethylhydrazid 
• 52377-70-5 5-nitroanthranilic acid hydrazide 
• 181813-16-1 2-amino-N-(4-methoxyphenyl)-5-nitrobenzamide 
• 3816-62-4 5-nitroanthranilic acid methyl ester 
• 220651-06-9 N-(2-amino-5-nitrobenzoyl)-β-alanine ethyl ester 
• 257944-69-7 2-amino-N-methyl-5-nitro-N-prop-2-ynyl-benzamide 
• 610-74-2 1,4-phenylenediamine-2-carboxylic acid 

Relevant articles and documents

Design, synthesis, and biological evaluation of rutacecarpine derivatives as multitarget-directed ligands for the treatment of Alzheimer's disease

A series of 3-amino-substituted rutacecarpine derivatives were synthesized to identify novel multitarget-directed ligands (MTDLs) for the treatment of Alzheimer's disease (AD). Biological evaluation showed that most of the synthesized compounds inhibited butyrylcholinesterase (BuChE) and exerted antioxidant effects. Among the synthesized compounds, 6n was subjected to further biological evaluation. Lineweaver–Burk plotting and molecular modeling illustrated that 6n bound simultaneously to the peripheral anionic site (PAS) and catalytic sites (CAS) of BuChE. Furthermore, 6n modulated Aβ aggregation; chelated biometals; presented good absorption, distribution, metabolism, excretion, and toxicity properties; and showed remarkable neuroprotective activity. Previous research has shown that the optimized compound 6n has considerable potential for development as an MTDL for the treatment of AD.

Green synthesis of novel phosphonate derivatives using ultrasonic irradiation

[Figure not available: see fulltext.] A novel and efficient procedure for the generation of quinazolinone phosphonate derivatives employing the reaction of euparin, isatin or its derivatives, primary amines, dialkyl acetylenedicarboxylates, trimethyl phosphite or triphenyl phosphite, and acidic solution of hydrogen peroxide in aqueous media at ambient temperature under ultrasonic irradiation was developed. Without ultrasonic irradiation, the reaction does not proceed and agitation of the reaction mixture is difficult. Some advantages of this procedure are: short time of reaction, high yields of products, easy isolation of products.

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.