63480-10-4

Basic information

• Product Name: 4-NITRO-ISATOIC ANHYDRIDE
• Synonyms: 7-NITRO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;4-NITRO-ISATOIC ANHYDRIDE;4-Nitroisatoic anhydride 97%;7-Nitro-2H-3,1-benzoxazine-2,4(1H)-dione, 7-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione;NSC 135175;7-nitro-1H-3,1-benzoxazine-2,4-dion;4-Nitroisatoicanhydride97%;2H-3,1-Benzoxazine-2,4(1H)-dione, 7-nitro-
• CAS NO: 63480-10-4
• Molecular Formula: C₈H₄N₂O₅
• Molecular Weight: 208.13
• Mol File: 63480-10-4.mol

Chemical Properties

• Appearance: /
• Density: 1.623 g/cm³
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-NITRO-ISATOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-ISATOIC ANHYDRIDE(63480-10-4)
• EPA Substance Registry System: 4-NITRO-ISATOIC ANHYDRIDE(63480-10-4)

Safety Data

• Hazardous Substances Data: 63480-10-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-NITRO-ISATOIC ANHYDRIDE is used as an intermediate in the synthesis of various pharmaceuticals due to its ability to participate in organic reactions such as nitration, halogenation, and Friedel-Crafts acylation. Its strong electron-withdrawing properties make it a valuable component in the development of new drugs and medicinal compounds.
Used in Dye Industry:
In the dye industry, 4-NITRO-ISATOIC ANHYDRIDE is utilized as an intermediate for the synthesis of dyes. Its unique structural properties and reactivity contribute to the creation of a wide range of dye products with diverse color characteristics and applications.
Used in Organic Reactions:
4-NITRO-ISATOIC ANHYDRIDE is used as a reagent in various organic reactions, including nitration, halogenation, and Friedel-Crafts acylation. Its strong electron-withdrawing properties make it an effective participant in these reactions, facilitating the formation of desired products and enhancing the overall efficiency of the processes.
Used in Heterocyclic Compound Preparation:
4-NITRO-ISATOIC ANHYDRIDE is employed as a reagent in the preparation of heterocyclic compounds. Its unique structural properties and reactivity enable the synthesis of a variety of heterocyclic compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.
Used as a Catalyst in Organic Transformations:
In the realm of organic transformations, 4-NITRO-ISATOIC ANHYDRIDE serves as an efficient catalyst. Its strong electron-withdrawing properties and versatile reactivity contribute to the acceleration of various organic reactions, improving the overall yield and selectivity of the processes.

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

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 619-17-0 4-Nitroanthranilic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 219491-92-6 2-amino-N-(4-methoxyphenyl)-4-nitrobenzamide 
• 791098-03-8 1-(2-amino-4-nitrobenzoyl)piperidine 
• 1348276-84-5 2-amino-N-(2-methoxybenzyl)-4-nitrobenzamide 
• 1254069-38-9 3-(methylthio)-1-phenyl-1H-indazol-6-amine 
• 1254069-41-4 4-(3-methylsulfanyl-1-phenyl-1H-indazol-6-ylcarbamoyl)piperidine-1-carboxylicacid tert-butyl ester 
• 1254069-36-7 N-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)piperidine-4-carboxamide hydrochloride 
• 1254069-39-0 6-nitro-1-phenyl-2,3-dihydro-1H-indazol-3-one 
• 67571-10-2 2-amino-4-nitro-N'-phenylbenzohydrazide 
• 1520077-97-7 2-amino-N-methoxy-4-nitrobenzamide 
• 128054-22-8 2-Amino-4-nitrobenzoesaeure-(4-nitrophenyl)ester 
• 128054-21-7 2-Amino-4-nitrobenzoesaeure-(4-methoxyphenyl)ester 
• 49565-62-0 2-(methylamino)-4-nitro-benzoic acid 
• 31930-18-4 2-amino-4-nitrobenzamide 
• 1520078-16-3 3-methoxy-7-nitro-2-phenylquinazolin-4(3H)-one 

Relevant articles and documents

Fluorescent biaryl uracils with C5-dihydro- And quinazolinone heterocyclic appendages in PNA

There has been much effort to exploit fluorescence techniques in the detection of nucleic acids. Canonical nucleic acids are essentially nonfluorescent; however, the modification of the nucleobase has proved to be a fruitful way to engender fluorescence. Much of the chemistry used to prepare modified nucleobases relies on expensive transition metal catalysts. In this work, we describe the synthesis of biaryl quinazolinone-uracil nucleobase analogs prepared by the condensation of anthranilamide derivatives and 5-formyluracil using inexpensive copper salts. A selection of modified nucleobases were prepared, and the effect of methoxy- or nitro- group substitution on the photophysical properties was examined. Both the dihydroquinazolinone and quinazolinone modified uracils have much larger molar absorptivity (~4-8×) than natural uracil and produce modest blue fluorescence. The quinazolinone-modified uracils display higher quantum yields than the corresponding dihydroquinazolinones and also show temperature and viscosity dependent emission consistent with molecular rotor behavior. Peptide nucleic acid (PNA) monomers possessing quinazolinone modified uracils were prepared and incorporated into oligomers. In the sequence context examined, the nitro-substituted, methoxy-substituted and unmodified quinazolinone inserts resulted in a stabilization (?Tm = +4.0/insert; +2.0/insert; +1.0/insert, respectively) relative to control PNA sequence upon hybridization to complementary DNA. All three derivatives responded to hybridization by the “turn-on” of fluorescence intensity by ca. 3-to-4 fold and may find use as probes for complementary DNA sequences.

New spiro pyrrole[2, 1-b]quinazolone derivative, preparation method and application thereof

The invention relates to a new spiro pyrrole[2, 1-b]quinazolone derivative, a preparation method and application thereof. The new spiro pyrrole[2, 1-b]quinazolone derivative is synthesized by using asimple method. The yield is high, the production cost is

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.

Amino evodiamine derivative and preparation method and application thereof

The invention discloses an amino evodiamine derivative and a preparation method and application thereof. A carboline compound and N-methyl-7-nitro isatoic anhydride are used for preparing a 2-nitro evodiamine derivative, and the 2-nitro evodiamine derivative is reduced to obtain the amino evodiamine derivative. A cytotoxicity experiment is performed by using a CCK-8 method, the anti-proliferationeffect of the compound on breast cancer MDA-MB-231 cells, colon cancer SW620 cells and normal liver LO2 cells is evaluated, and cell apoptosis detection is performed by using FITC/PI double staining;experiments show that compared with evodiamine, the compound 2-NH2-EVO has a very strong inhibition effect on breast cancer cells MDA-MB-231, the IC50 value is 0.79 uM, meanwhile, cell apoptosis can be remarkably induced, and the compound 2-NH2-EVO is expected to be developed into an anti-cancer drug with potential.

Amino evodiamine polymer micelle as well as preparation method and application thereof

The invention discloses an amino evodiamine polymer micelle as well as a preparation method and application thereof. The preparation method comprises the following steps: preparing a 2-nitro evodiamine derivative from a carboline compound and N-methyl-7-nitro isatoic anhydride, reducing the 2-nitro evodiamine derivative to obtain an amino evodiamine derivative, and reacting a polymer with amino evodiamine to prepare an amino evodiamine polymer conjugate; and then carrying out self-assembly on the amino evodiamine polymer conjugate to obtain the amino evodiamine polymer micelle. The water solubility and bioavailability of a drug are improved, the drug is combined with a nanotechnology, a nano drug loading system is developed for drug delivery, and the nano drug can be passively enriched intumor tissues in a targeting manner through an EPR effect.

Doxorubicin-loaded polymeric micelle as well as preparation method and application thereof

The present invention discloses a doxorubicin-loaded polymeric micelle as well as a preparation method and application thereof. Novel amino evodiamine is adopted to react with polyethylene glycol, a micelle obtained by self-assembly is used as a carrier to load doxorubicin, a prepared mPEG-CO-NH-EVO micelle and a mPEG-CO-NH-EVO-OCH3 micelle have low toxicity to normal hepatocytes so that the two amphipathic polymeric micelles are used as carriers to load DOX to prepare DOX-loaded polymeric micelles, namely a mPEG-CO-NH-EVO/DOX micelle and a mPEG-CO-NH-EVO-OCH3/DOX micelle, and DOX enters hydrophobic shells of the micelles due to the dialysis effect; shapes of the micelles are represented by using a transmission electron microscope and a scanning electron microscope, and the drug loading efficiency and encapsulation efficiency of DOX are tested and calculated by using an ultraviolet spectrophotometer; and finally, evaluating the cytotoxicity by using a CCK-8 method. Shown by cytotoxicity tests, a DOX-loaded polymer has an effect on inhibiting breast cancer cells and particularly has greatly reduced toxicity to the normal hepatocytes.

Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita

To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.

Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: Preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives

A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–buildup strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project.

METHOD OF PRODUCING NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a chemical compound production method realizing easy and high-yield production of a nitrogen-containing heterocyclic compound useful as a synthetic intermediate and the like in many fields such as medicine, agriculture and synthetic resin additives. SOLUTION: In the production method, an ortho-substituted benzene azide derivative represented by formula (1) is reacted with carbon dioxide in the presence of a reductant to obtain a compound represented by formula (2). [R is H and/or a substituent; A is an intramolecular cyclizable group; and B is a divalent linking group of C, N and O. COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.