321-69-7

Basic information

• Product Name: 5-Fluoroisatonic anhydride
• Synonyms: 6-FLUORO ISATIN ANHYDRIDE;5-FLUOROISATOIC ANHYDRIDE;5-FLUOROISATONIC ANHYDRIDE;6-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE;6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione;6-fluoro-1H-3,1-benzoxazine-2,4-dione;6-fluoro-1H-3,1-benzoxazine-2,4-quinone;6-Fluorobenzo[d][1,3]oxazine-2,4-dione
• CAS NO: 321-69-7
• Molecular Formula: C₈H₄FNO₃
• Molecular Weight: 181.12
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 321-69-7.mol
• Article Data: 35

Chemical Properties

• Melting Point: 259-262°C
• Appearance: /
• Density: 1.502 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: 5-Fluoroisatonic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoroisatonic anhydride(321-69-7)
• EPA Substance Registry System: 5-Fluoroisatonic anhydride(321-69-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 321-69-7(Hazardous Substances Data)

Usage

Chemical Properties

Dark yellow Solid

Preparation

5-Fluoroisatonic anhydride is prepared from 5-fluoro indole (9d) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature. 1 H NMR (DMSO-d6): δ11.19 (s, br., 1H), 7.36 (dd, J = 8.4, 2.6 Hz, 1H), 6.87 (dt, J = 8.4, 2.2 Hz, 1H), 6.74 (dd, J = 9.3, 2.2 Hz, 1H).

Upstream product

• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 75-44-5 phosgene 
• 446-08-2 2-amino-5-fluorobenzoic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 399-52-0 5-fluoro-1H-indole 
• 530-62-1 1,1'-carbonyldiimidazole 
• 371-40-4 4-fluoroaniline 
• 201230-82-2 carbon monoxide 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 124-38-9 carbon dioxide 
• 455-38-9 3-fluorobenzoic acid 
• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 76361-57-4 2-amino-N-(4-ethoxy-3-thienyl)-5-fluorobenzamide 
• 144155-10-2 7-Fluoro-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 
• 76746-19-5 5-fluoroanthranilic hydrazide 
• 477933-12-3 1-(2-cyclopropylethyl)-6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 881312-97-6 2-(2'-ethoxybiphenyl-4-yl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile 
• 881312-98-7 4-chloro-2-(2'-ethoxybiphenyl-4-yl)-6-fluoroquinoline-3-carbonitrile 
• 144155-39-5 1-[(E)-3-Dimethylamino-propylimino]-7-fluoro-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one 
• 888952-51-0 2-amino-5-fluoro-N'-(2-fluorophenyl)benzohydrazide 
• 881313-55-9 2-(2'-ethoxy-3-fluorobiphenyl-4-yl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile 
• 749865-72-3 6-fluoro-1-(4-fluoro-benzyl)-1H-benzo[d][1,3]oxazine-2,4-dione 
• 773846-62-1 2-amino-5-fluoro-N-methylbenzamide 
• 1155900-54-1 2-amino-N-(4-sec-butylphenyl)-5-fluorobenzamide 
• 881311-60-0 2-(4-bromophenyl)-6-fluoro-4-hydroxyquinoline-3-carbonitrile 
• 881313-83-3 6-fluoro-4-hydroxy-2-(4-propylphenyl)quinoline-3-carbonitrile 

Relevant articles and documents

Preparation method of flumazenil

The invention discloses a preparation method of flumazenil, and belongs to the field of medicine synthesis. The method comprises the following steps: by taking 5-fluoro-2-nitrobenzoic acid as a raw material, carrying out condensation on 5-fluoro-2-nitrobenzoic acid and sarcosine ester, and then carrying out ring closing while reducing, so as to obtain 7-fluoro-3, 4-dihydro-4-methyl-1H-[1, 4] benzodiazepine-2, 5-diketone; and finally, carrying out halogenation and cycloaddition reaction to obtain flumazenil. According to the novel synthesis method of the flumazenil key intermediate 7-fluoro-3, 4-dihydro-4-methyl-1H-[1, 4] benzodiazepine-2, 5-diketone, provided by the invention, a green synthesis process is adopted, an intramolecular cyclization reaction is performed while a nitro group is reduced, and compared with a known flumazenil synthesis method, a strong oxidant, a highly toxic reagent (such as ethyl chloroformate) and the like are not needed, and the yield is higher.

Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam

An anionic annulation strategy employing isatoic anhydrides and a wide assortment of enolizable partners was developed to afford over 80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented privileged template. Multiple factors governing the efficiency of the transformation were determined, resulting in a reliable and tunable synthetic platform applicable for a broad range of substrates with variable deprotonation susceptibility, such as tetramic and tetronic acids, cyclic 1,3-diketones, and cycloalkanones. Application to the synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis of the alkaloid in three steps and a 36% overall yield.

Dihydroquinozolinone antiport process blocking agent, and preparation method and application thereof

The invention belongs to the field of pharmaceutical and chemical industry, and relates to dihydroquinozolinone antiport process blocking agent, and a preparation method and application thereof, in particular to a novel dihydroquinozolinone antiport process blocking agent compound, a medicinal salt, isomer, hydrate and solvate thereof, application of the compound and the medicinal salt, isomer, hydrate and solvate thereof to preparation of drugs for preventing and/or first aiding diseases caused by ribosome-inactivating proteins, and application of the compound and the medicinal salt, isomer,hydrate and solvate thereof to preparation of drugs for preventing and/or curing diseases caused by enterovirus, filoviridae or polyomavirus. The compound can effectively resist II-type ribosome-inactivating protein poisoning and/or the diseases caused by enterovirus, filoviridae or polyomavirus.