15028-10-1

Basic information

• Product Name: INDAN-1,2-DIONE-2-OXIME
• Synonyms: SPECS AE-508/36398054;2-OXIMINO-1-INDANONE;INDAN-1,2-DIONE-2-OXIME;1,2-indandione-2-oxime;2-(Hydroxyimino)-2,3-dihydro-1H-inden-1-one;1,2-Indandione-2-oxime 97%
• CAS NO: 15028-10-1
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Mol File: 15028-10-1.mol

Chemical Properties

• Melting Point: 209 °C (dec.)(lit.)
• Boiling Point: 345.9 °C at 760 mmHg
• Flash Point: 163 °C
• Appearance: /solid
• Density: 1.34 g/cm³
• Vapor Pressure: 2.26E-05mmHg at 25°C
• Refractive Index: 1.65
• PKA: 8.96±0.20(Predicted)
• CAS DataBase Reference: INDAN-1,2-DIONE-2-OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: INDAN-1,2-DIONE-2-OXIME(15028-10-1)
• EPA Substance Registry System: INDAN-1,2-DIONE-2-OXIME(15028-10-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 15028-10-1(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
INDAN-1,2-DIONE-2-OXIME is utilized as a reagent for the detection of nitrite ions in environmental samples. Its role in analytical chemistry is pivotal for monitoring and assessing the presence of these ions, which are significant in various environmental contexts.
Used in Organic Synthesis:
In the field of organic synthesis, EDDN serves as a precursor for the synthesis of other organic compounds. Its chemical properties make it a valuable intermediate in the creation of a range of products, contributing to the development of new materials and chemical entities.
Given the potential hazards associated with EDDN, including its toxic and irritant nature, it is imperative that this chemical compound is handled with appropriate safety measures in place across all applications and industries where it is utilized.

InChI:InChI=1/C9H7NO2/c11-9-7-4-2-1-3-6(7)5-8(9)10-12/h1-4,12H,5H2/b10-8+

Upstream product

• 544-16-1 n-Butyl nitrite 
• 83-33-0 inden-1-one 
• 463-04-7 n-Amyl nitrite 
• 110-46-3 isopentyl nitrite 
• 16214-27-0 indan-1,2-dione 
• 645-45-4 hydrocinnamic acid chloride 
• 7647-01-0 hydrogenchloride 
• 10544-72-6 dinitrogen tetraoxide 
• 71-43-2 benzene 

Downstream Products

• 13575-72-9 2-amino-1-indanol 
• 6941-16-8 2-AMINO-2,3-DIHYDRO-1H-INDEN-1-ONE HYDROCHLORIDE 
• 16214-27-0 indan-1,2-dione 
• 2975-41-9 2,3-dihydro-1H-inden-2-amine 
• 94077-16-4 (+)-(1S,2S)-2-(2,3-dimethoxybenzylideneamino)-5-methoxyindan-1-ol 
• 94077-16-4 (1R,2R)-2-{[1-(2,3-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-5-methoxy-indan-1-ol 
• 94077-06-2 (+)-(1S,2S)-2-(3,4-dimethoxybenzylideneamino)-5-methoxyindan-1-ol 
• 94077-06-2 (1R,2R)-2-{[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-5-methoxy-indan-1-ol 
• 94077-21-1 (1R,2R)-2-(3,4-Dimethoxy-benzylamino)-5-methoxy-indan-1-ol 
• 94077-21-1 (+)-(1S,2S)-2-(3,4-dimethoxybenzylamino)-5-methoxyindan-1-ol 
• 94077-05-1 (-)-(1R,2R)-2-benzylideneamino-5-methoxyindan-1-ol 
• 94077-05-1 (1S,2S)-5-Methoxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-indan-1-ol 
• 94077-20-0 (+)-(1S,2S)-2-benzylamino-5-methoxyindan-1-ol 
• 94077-44-8 (R)-3,3,3-Trifluoro-N-((1R,2R)-1-hydroxy-5-methoxy-indan-2-yl)-2-methoxy-2-phenyl-propionamide 

Relevant articles and documents

A novel one-step conversion of 3,3,3-Triphenylpropionic acid to 10- cyano-10-phenyl-9-anthrone

3,3,3-Triphenylpropionic acid transformed to 10-cyano-10-phenyl-9- anthrone when it was treated in consecutive order with trifluoroacetic anhydride and sodium nitrite in trifluoroacetic acid.

Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone-Thioimidazolidine-Oxindoles

This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone-thioimidazolidine-oxindoles bearing two adjacent spiro-quaternary stereocenters in good to excellent yields with excellent diastereo- and enantioselectivities. Versatile transformations of the products into other potential bioactive bispirocyclic heterocycles have also been demonstrated.

Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones

A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient

Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.

Synthesis of 2-(Cyanomethyl)benzoic Esters via Carbon-Carbon Bond Cleavage of Indanones

A novel synthesis of 2-(cyanomethyl)benzoic esters from indanone derivatives has been established. This reaction proceeds via a deprotonation of alcohols with a chemical base, followed by a nucleophilic addition to indanones and Beckmann fragmentation. In addition, this reaction could also work under electrochemical conditions, and no external chemical bases were needed. This mild method offers a novel strategy for the late-stage functionalization of various natural alcohols.

Cu-catalyzed coupling of indanone oxime acetates with thiols to 2,3-difunctionalized indenones

A Cu-catalyzed coupling reaction of indanone oxime acetates with thiols has been developed for the synthesis of 2,3-functionalized 1-indenones. This protocol has several features including easy mild reaction conditions, stabilized enamine products, good t

Preparation method of 2-aminoindan derivative

The invention discloses a preparation method of a 2-aminoindan derivative. The preparation method comprises the following steps: with a 1-indanone derivative as a starting raw material, carrying out oximation reaction, and synchronously reducing carbonyl and hydroxyl oxime under the catalysis of Lewis acid such as aluminum chloride in the presence of a boron metal reducing agent, so as to obtain the 2-aminoindan derivative. The invention further provides the 2-aminoindan derivative prepared by virtue of a synthetic method and a corresponding intermediate derivative. Compared with a synthetic method of the 2-aminoindan derivative in the prior art, the synthetic method disclosed by the invention has the beneficial effects that (1) only two reaction steps are adopted, and the reaction steps are obviously less than the reaction steps in the prior art; (2) the cost is relatively low, the operation is simple and convenient, and the yield is high; and (3) the preparation method is suitable for large-scale industrial production and has relatively good application prospects.

Rapid Construction of Complex 2-Pyrrolines through Lewis Acid-Catalyzed, Sequential Three-Component Reactions via in Situ-Generated 1-Azaallyl Cations

The first Sc(OTf)3-catalyzed dehydration of 2-hydroxy oxime ethers to generate benzylic stabilized 1-azaallyl cations, which are captured by 1,3-carbonyls, is described. A subsequent addition of primary amines in a sequential three-component re

INDOLAMID DERIVATIVES WHICH POSSESS GLYCOGENPHOSPHORYLASE INHIBITORY ACTIVITY

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Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors

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