3340-93-0

Usage

Chemical classification

Polycyclic aromatic hydrocarbon compound

Physical state

Yellow solid

Molecular weight

263.33 g/mol

Known properties

Potent mutagenic and carcinogenic

Usage

Laboratory research (inducing DNA damage, studying mutagenesis and carcinogenesis mechanisms), organic dyes and pigments component

Health risks

Increased risk of developing cancer (inhalation or skin contact)

Concerns

Occupational and environmental health and safety

InChI:InChI=1/C18H13N/c1-12-14-7-4-5-9-16(14)19-17-11-10-13-6-2-3-8-15(13)18(12)17/h2-11H,1H3

Upstream product

• 135-88-6 N-Phenyl-2-naphthylamine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 574-19-6 1-(2-hydroxy-1-naphthyl)ethan-1-one 
• 62-53-3 aniline 
• 32316-92-0 naphthalene-2-boronic acid 
• 551-93-9 2-aminoacetophenone 
• 580-13-2 2-bromonaphthalene 

Downstream Products

• 96003-38-2 N'-benz[a]acridin-12-ylmethylene-N,N-dimethyl-p-phenylenediamine 
• 63021-46-5 12-(3-nitro-trans-styryl)-benz[a]acridine 
• 63019-59-0 4-(2-benzo[a]acridin-12-yl-vinyl)-N,N-dimethyl-aniline 
• 104134-85-2 N-benz[a]acridin-12-ylmethylene-N',N'-dimethyl-p-phenylenediamine-N-oxide 
• 13471-30-2 7H-benzo[a]acridin-12-one 
• 101-81-5 Diphenylmethane 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 1609956-64-0 (benzo[a]acridin-12-yl)methyl 4-nitrobenzoate 
• 1609956-63-9 (benzo[a]acridin-12-yl)methyl 4-vinylbenzoate 
• 1609956-62-8 (benzo[a]acridin-12-yl)methyl 4-methoxybenzoate 
• 1609956-61-7 (benzo[a]acridin-12-yl)methyl 4-methylbenzoate 
• 1609956-60-6 (benzo[a]acridin-12-yl)methyl benzoate 
• 1609956-59-3 (benzo[a]acridin-12-yl)methyl 2-phenylacetate 
• 34331-96-9 12-(bromomethyl)benzo[a]acridine 

Relevant academic research and scientific papers

Tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C-N Coupling: Synthesis of Acridines at Room Temperature

Herein, a facile intramolecular cyclization of 2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan-Evans-Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted acridines from readily available 2-amino phenyl ketones and aryl boronic acids at room temperature.

Benzo[a]acridinylmethyl esters as pH sensitive fluorescent photoactive precursors: Synthesis, photophysical, photochemical and biological applications

A newsworthy class of carboxylate esters based on the (benzo[a]acridin-12- yl)methyl (BAM) chromophore has been shown to perform dual functions as a "pH sensitive fluorescent probe" and a "phototrigger" for acids. The photophysical properties of all the BAM ester conjugates were investigated and found to be highly sensitive to solvent polarity, H-bonding capability and pH of the environment. On irradiation using UV light (≥410 nm), BAM ester conjugates underwent heterolytic cleavage of C-O bonds resulting in efficient release of carboxylic and amino acids. Interestingly, the newly synthesized BAM chromophore was also explored for the construction of a drug delivery system (DDS). In the current DDS, the BAM chromophore plays two important roles: (i) a "fluorophore" for cell imaging and (ii) a "phototrigger" for the drug release. In vitro biological studies revealed that the newly developed BAM based DDS has a good biocompatibility, cellular uptake properties and efficient photoregulated anticancer drug release ability. the Partner Organisations 2014.

Rapid synthesis of acridines using microwave

Microwave irradiation for several minutes caused reaction of diarylamines with carboxylic acids in the presence of zinc chloride to give 9-substituted acridines in good yield.