4693-00-9

Basic information

• Product Name: 3,5-DICHLOROISATOIC ANHYDRIDE
• Synonyms: 3,5-DICHLOROISATOIC ANHYDRIDE;6,8-DICHLORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;6,8-DICHLOROISATOIC ANHYDRIDE;6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione;6,8-dichloro-1H-3,1-benzoxazine-2,4-dione;6,8-dichloro-1H-3,1-benzoxazine-2,4-quinone;2H-3,1-Benzoxazine-2,4(1H)-dione, 6,8-dichloro-
• CAS NO: 4693-00-9
• Molecular Formula: C₈H₃Cl₂NO₃
• Molecular Weight: 232.02
• EINECS: 225-149-0
• Mol File: 4693-00-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.654 g/cm³
• Refractive Index: 1.613
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-DICHLOROISATOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DICHLOROISATOIC ANHYDRIDE(4693-00-9)
• EPA Substance Registry System: 3,5-DICHLOROISATOIC ANHYDRIDE(4693-00-9)

Safety Data

• Hazardous Substances Data: 4693-00-9(Hazardous Substances Data)

Usage

General Description

3,5-Dichloroisatoic Anhydride is a chemical compound used in various industrial and scientific applications. Its molecular formula is C8H3Cl2NO3 and it appears as an off-white crystalline powder. It is relatively stable but may decompose upon heating, while it is also known to be incompatible with strong oxidizing agents. The exact properties and potential health effects of this chemical are not well-studied, therefore it should be handled with care. It's largely used in the pharmaceutical industry and in scientific research, often playing a role as a reagent in organic synthesis.

InChI:InChI=1/C8H3Cl2NO3/c9-3-1-4-6(5(10)2-3)11-8(13)14-7(4)12/h1-2H,(H,11,13)

Upstream product

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• 91-56-5 indole-2,3-dione 
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• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 56821-48-8 2-Amino-3,5-dichloro-N-morpholin-4-yl-benzamide 
• 250124-66-4 2-amino-3,5-dichloro-N-[4-(6-ethoxy-benzothiazol-2-ylsulfanyl)-phenyl]-benzamide 
• 1422677-85-7 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(diethyl-λ⁴-sulfanylidene)carbamoyl]phenyl]-5-(trifluoromethyl)-2H-pyrazole-3-carboxamide 
• 1422677-86-8 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(bis-2-propyl-λ⁴-sulfanylidene)carbamoyl]phenyl]-5-(trifluoromethyl)-2H-pyrazole-3-carboxamide 
• 1422677-58-4 2-amino-N-(bis-(2-propyl)-λ⁴-sulfanylidene)-3,5-dichlorobenzamide 
• 1422677-59-5 2-amino-3,5-dichloro-N-(diethyl-λ⁴-sulfanylidene)benzamide 

Relevant articles and documents

Synthesis, insecticidal activities, and SAR studies of novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives

Diamide compounds such as chlorantraniliprole, a famous anthranilic diamide insecticide targeting the insect ryanodine receptor (RyR), have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials. With the aim of discovering new heterocyclic pesticides used for crop protection, based on the structural information of compound M from the reported pharmacophore-based virtual screening for RyR insecticides and diamide compound, a series of new heterocyclic mono-, di-, and tri-amide derivatives containing piperazine moiety have been synthesized in this paper. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and HRMS. Compound M was firstly validated for insecticidal activities, and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm. The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials, particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8g, 14a, 15a, 15g, 15i, 15j, 15k, 15l, and 15m could be used as new insecticidal leading structures for further study (e.g., towards diamondback moth, 15i-15m LC50: 0.0022?0.0081 mg/L). The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.

Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives

To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.

Palladium-Catalyzed Cyclization Reaction of o-Iodoanilines, CO2, and CO: Access to Isatoic Anhydrides

Isatoic anhydrides, a class of valuable synthetic intermediates and RNA structure probing reagents, are usually prepared with highly toxic phosgene or stoichiometric oxidants. Herein we report a highly selective palladium-catalyzed cyclization reaction for the efficient synthesis of isatoic anhydrides from readily available o-iodoanilines, CO2, and CO. The reaction proceeds under mild conditions and is redox-neutral. Both CO2 and CO are indispensable C1 building blocks for this catalytic reaction.