5339-80-0

Basic information

• Product Name: 3,3-bis[4-(dimethylamino)phenyl]phthalide
• Synonyms: 3,3-bis[4-(dimethylamino)phenyl]phthalide;1,1-Bis[4-(dimethylamino)phenyl]isobenzofuran-3(1H)-one;3,3-Bis[4-(dimethylamino)phenyl]isobenzofuran-1(3H)-one;3,3-Bis[4-(N,N-dimethylamino)phenyl]phthalide;1(3H)-Isobenzofuranone, 3,3-bis(4-(dimethylamino)phenyl)-;Ai3-17348;Einecs 226-274-3
• CAS NO: 5339-80-0
• Molecular Formula: C₂₄H₂₄N₂O₂
• Molecular Weight: 372.45956
• EINECS: 226-274-3
• Mol File: 5339-80-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 549.8°Cat760mmHg
• Flash Point: 286.3°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 3.87E-12mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 3,3-bis[4-(dimethylamino)phenyl]phthalide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-bis[4-(dimethylamino)phenyl]phthalide(5339-80-0)
• EPA Substance Registry System: 3,3-bis[4-(dimethylamino)phenyl]phthalide(5339-80-0)

Safety Data

• Hazardous Substances Data: 5339-80-0(Hazardous Substances Data)

Usage

General Description

3,3-bis[4-(dimethylamino)phenyl]phthalide, also known as crystal violet lactone, is a synthetic organic compound commonly used as a colorimetric indicator in chemical analysis. It has a molecular formula of C31H30N2O3 and a molecular weight of 478.58 g/mol. This chemical compound is known for its blue to colorless reversible reaction in the presence of acids or bases, making it useful as a pH indicator. It is also used in carbonless copy paper as a component of the color-forming reaction. Additionally, it has been studied for its potential application in the development of fluorescent probes and sensors for bioimaging and environmental monitoring. Despite its versatility, caution should be exercised when handling 3,3-bis[4-(dimethylamino)phenyl]phthalide, as it is classified as a hazardous chemical with potential health and environmental risks.

InChI:InChI=1/C24H24N2O2/c1-25(2)19-13-9-17(10-14-19)24(18-11-15-20(16-12-18)26(3)4)22-8-6-5-7-21(22)23(27)28-24/h5-16H,1-4H3

Upstream product

• 85-44-9 phthalic anhydride 
• 121-69-7 N,N-dimethyl-aniline 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 21528-31-4 2-(4-(dimethylamino)benzoyl)benzoic acid 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 74317-52-5 4,4-bis-(p-dimethylaminophenyl)-3,4-dihydro-1(2H)-phthalazinone 
• 88-95-9 Phthaloyl dichloride 
• 119-67-5 o-carboxybenzaldehyde 
• 7647-01-0 hydrogenchloride 
• 74415-34-2 7-dimethylamino-4b-(p-dimethylaminophenyl)benzazulen-10-one 
• 108-24-7 acetic anhydride 
• 62632-80-8 2-(4,4'-bis-dimethylamino-benzhydryl)-benzoic acid 
• 76763-92-3 4,4-Bis-(4-dimethylamino-phenyl)-4H-phthalazin-1-one 

Downstream Products

• 1552-42-7 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone 
• 29199-07-3 6-amino-3,3-bis(4-dimethylaminophenyl)phthalide 
• 74453-96-6 methyl o--methyl benzoate 
• 129-73-7 bis(4-dimethylaminophenyl)phenylmethane 
• 121-69-7 N,N-dimethyl-aniline 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 65-85-0 benzoic acid 
• 62632-80-8 2-(4,4'-bis-dimethylamino-benzhydryl)-benzoic acid 
• 29199-08-4 6-nitro-3,3-bis(4-dimethylaminophenyl)phthalide 
• 74317-52-5 4,4-bis-(p-dimethylaminophenyl)-3,4-dihydro-1(2H)-phthalazinone 
• 21528-31-4 2-(4-(dimethylamino)benzoyl)benzoic acid 
• 2491-74-9 N,N-dimethyl-4-(4-nitrophenylazo)aniline 

Relevant articles and documents

Malachite green derivatives with double protein activation sites as well as synthesis method and application of malachite green derivatives

The invention relates to malachite green derivatives with double protein activation sites as well as a synthesis method and application of the malachite green derivatives. The structural formula of the malachite green derivative is shown as (I). The synthetic method has the advantages of high total yield, simple reaction conditions, convenience in operation, large-scale preparation, wide substrate selection range and the like. The derivative has the characteristic of two protein activation sites, and can be applied to the fields of fluorescence imaging, fluorescent probes, stimulation response materials and the like.

A NOVEL REGIOSPECIFIC INTRAMOLECULAR CYCLOADDITION OF AN AROMATIC RING. MOLECULAR ORBITAL STUDY OF CONJUGATED KETENES THERMALLY GENERATED FROM SIX-MEMBERED α-MONOCARBONYL AZO-COMPOUNDS

When a methylene dichloride solution containing 4,4-diarylphthalazin-1(4H)-one (3) was warmed above -50 deg C, nitrogen extrusion occurred to result in the formation of the quinonoid ketene (19).The quinonoid ketene thus generated underwent a facile and regiospecific intramolecular ?4a + ?2a> cycloaddition with NN-dimethylaniline to afford a norcaradiene (22), followed by ring opening to an azulenone derivative (14).It was found, however, that this process takes place only with an aromatic ring bearing strong electron-donating substituents such as dialkylamino groups.FMO analyses based on the model system calculated by the CNDO/2 method showed that the dominant HOMO-LUMO interaction in the transition state should involve the HOMO of NN-dialkylaniline and LUMO of the quinonoid ketene.Thus, the in-plane ?*-orbital induces the orthogonal approach of the two components favouring an antarafacial pathway and the cyclisation is initiated by preferential bond formation between the central carbon of the ketene moiety and the para-carbon of NN-dialkylaniline to result in the formation of (22).

Substituent effects and structural limitations in the conversion of 3,3-diaryl-phthalides to 4,4-diaryl-3,4-dihydro-1(2H)-phthalazinones

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