28752-91-2

Basic information

• Product Name: 2-(dimethylaminomethylidene)indene-1,3-dion
• Synonyms: 2-(dimethylaminomethylidene)indene-1,3-dion;2-(dimethylaminomethylidene)indene-1,3-dione;2-[(dimethylamino)methylidene]-1H-indene-1,3(2H)-dione
• CAS NO: 28752-91-2
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.23
• EINECS: -0
• Mol File: 28752-91-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 324.7°C at 760 mmHg
• Flash Point: 142.6°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 0.000242mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 2-(dimethylaminomethylidene)indene-1,3-dion(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(dimethylaminomethylidene)indene-1,3-dion(28752-91-2)
• EPA Substance Registry System: 2-(dimethylaminomethylidene)indene-1,3-dion(28752-91-2)

Safety Data

• Hazardous Substances Data: 28752-91-2(Hazardous Substances Data)

Usage

Molecular structure

2-(dimethylaminomethylidene)indene-1,3-dione

Type of compound

Organic compound

Use

Reagent in organic synthesis

Characteristic features

Indene-1,3-dione core with a dimethylaminomethylidene substituent

Reactions

Ability to react with a variety of nucleophiles, such as alkoxides, amines, and enolates

Applications

Building block in the synthesis of pharmaceuticals and agrochemicals, formation of heterocyclic compounds (e.g. pyrazoles, pyrazines, and pyrroles), precursor in the synthesis of various materials (e.g. polymers, metal-organic frameworks)

InChI:InChI=1/C12H11NO2/c1-13(2)7-10-11(14)8-5-3-4-6-9(8)12(10)15/h3-7H,1-2H3

Upstream product

• 81054-58-2 Kalium-(2-chlor-1,3-dioxo-indan-2-yl)-methansulfonat 
• 81054-40-2 1,3,4-Dioxathian-2,6-dispiro-bis<2'-(1,3-dioxo-indan)>-4,4-dioxid 
• 124-40-3 dimethyl amine 
• 81066-47-9 (2-Chlor-1,3-dioxo-indan-2-yl)-methansulfonylchlorid 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 496024-68-1 2-[(4-phenylpyrazol-3-ylamino)methylene]-1,3-indenedione 
• 658693-49-3 2-[(3-phenylpyrazol-5-ylamino)methylene]-1,3-indenedione 
• 1318754-02-7 2-[2-(1,3-diphenyl-1,3-dihydro-2H-benzimidazol-2-ylidene)ethylidene]-1H-indene-1,3(2H)-dione 
• 1224734-29-5 2-((2-(2-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-30-8 2-((2-(3-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-27-3 2-((2-p-tolylhydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 1224734-28-4 2-((2-(4-isopropylphenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 53162-10-0 1-phenylindeno<1,2-c>pyrazol-4(1H)-one 
• 650597-81-2 1H-indeno[1,2-b]pyridine-2,5-dione 
• 81054-84-4 2-((2-(4-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione 
• 53162-69-9 2-(N'-phenylhydrazinomethylene)indane-1,3-dione 

Relevant articles and documents

Indenopyrazole oxime ethers: Synthesis and β1-adrenergic blocking activity

This paper reports the synthesis and cardiac activity of new β-blockers derived from (Z/E)-indeno[1,2-c]pyrazol-4(1H)-one oximes (5a,b). The latter compounds were allowed to react with epichlorohydrin, followed by reacting the oxiranyl derivatives formed

Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors

Biological screening of (hetero)aromatic compounds allowed the identification of some novel inhibitors of Aβ1-40 aggregation, bearing indane and indole rings as common scaffolds. Molecular decoration of lead compounds led to inhibitors exhibiting a potency, measured by the Thioflavin T fluorimetric assay, ranging from high to low micromolar IC50. The 2-(p-isopropylphenyldiazenylmethylene)indolone derivative 6c resulted as the most potent aggregation inhibitor exhibiting an IC50 of 1.4?μM, with complete lack of fibril formation as confirmed by transmission electron microscopy. Structure-activity relationships suggested that binding to the Aβ peptide may be largely guided by π-stacking and hydrogen bond interactions.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. I. Synthesis of 1,5-Disubstituted 4-Acylpyrazoles

Reaction of open-chain and cyclic sym-1,3-diones with N,N-dimethylformamide dimethyl acetal gave, generally in high yield, a series of sym-2-dimethylaminomethylene-1,3-diones which reacted with phenylhydrazine and methylhydrazine to afford, generally in satisfactory yield, a number of 1,5-disubstituted 4-acylpyrazoles.The applications and limits of this new pyrazole synthesis are presented and discussed.