46710-42-3

Basic information

• Product Name: 2,6-Anthracenediamine
• CAS NO: 46710-42-3
• Molecular Formula: C14H12N2
• Molecular Weight: 208.263
• Mol File: 46710-42-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,6-Anthracenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Anthracenediamine(46710-42-3)
• EPA Substance Registry System: 2,6-Anthracenediamine(46710-42-3)

Safety Data

• Hazardous Substances Data: 46710-42-3(Hazardous Substances Data)

Usage

General Description

2,6-Anthracenediamine, also known as 2,6-diaminoanthraquinone, is a chemical compound with the molecular formula C14H12N2. It is a type of diamine and anthracene derivative, and is used in the production of dyes and pigments. 2,6-Anthracenediamine is a dark gray to black solid at room temperature, and is insoluble in water. It is commonly used in the dyeing of textiles and has also been investigated for its potential use in organic electronic materials. The compound is known to be toxic if ingested or inhaled, and can cause skin and eye irritation upon contact. Overall, 2,6-Anthracenediamine is a versatile chemical with various industrial applications, but caution should be exercised in its handling and use.

Upstream product

• 96886-97-4 3,7-diamino-10,11-dihydro-5H-dibenzocyclohepten-5-one 
• 131-14-6 2,6-diamino-9,10-anthraquinone 
• 1335230-35-7 N,N'-(anthracene-2,6-diyl)dihexanamide 
• 87120-50-1 2,6-diaminoanthracen-9(10H)-one 
• 1335230-37-9 di-t-butyl (anthracene-2,6-diyl)dicarbamate 
• 1335230-36-8 C₃₄H₄₂N₂O₁₀ 
• 1210-35-1 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one 
• 633-70-5 2,6-dibromoanthraquinone 
• 96886-98-5 3,7-dinitro-10,11-dihydro-5H-dibenzocyclohepten-5-one 

Downstream Products

• 232921-67-4 2,6-bis(2,3-dihydroxybenzamido)anthracene 
• 186517-01-1 2,6-dibromoanthracene 

Relevant articles and documents

Excited-state intermolecular proton transfer dependent on the substitution pattern of anthracene-diurea compounds involved in fluorescent ON1-OFF-ON2 response by the addition of acetate ions

We report anthracene-diurea compounds which behave as anion sensors based on the fluorescence emission regulated by the substitution position on the anthracene ring. Anthracene-diurea compounds exhibit different excited-state intermolecular proton transfer (ESIPT) reactions depending on the pattern of the substituents. Three new anthracene-diurea compounds that have two phenylurea groups substituted at different positions on anthracene were synthesized. These compounds formed complexes with acetate ions through intermolecular hydrogen bonding between N-H and CO moieties in the ground state. The positions of the substituents greatly affected the excited-state intermolecular proton transfer. 1,5BPUA with urea groups at the 1 and 5 positions exhibited ESIPT reaction, which is energetically favorable for tautomer formation, in the presence of TBAAc. In contrast, 2,6BPUA with urea groups at low-electron-density positions (2 and 6 positions) showed no ESIPT reaction due to the inversion of the lowest unoccupied molecular orbital (LUMO) energy levels of the normal and tautomer states. Detailed spectroscopic measurements showed that the LUMO energy level of the normal form was lowered because the urea group acted as an electron-withdrawing group. In addition, 9,10BPUA exhibited strong electronic interactions between the two phenylurea moieties at the 9 and 10 positions, resulting in an ON1-OFF-ON2 response for acetate ions. Our findings offer guidelines for the molecular design of materials with anthracene moieties based on the substitution patterns of anthracene derivatives.

An optimized method for the synthesis of 2,6-diaminoanthracene

The reduction of 2,6-diaminoanthraquinone to 2,6-diaminoanthracene was examined under a variety of conditions. Direct reduction using zinc powder gave a mixture of the target product and 9,10-dihydro-2,6-diaminoanthracene under all the conditions examined. Protection of the starting amine, followed by borohydride reduction and deprotection, gave the target product in 14-50% yield. Finally, tin powder was used to reduce the anthraquinone to 2,6-diaminoanthrone in quantitative yield. This compound was further reduced to the target 2,6-diaminoanthracene in 55-65% yield.

Regiospecific Formation of Anthracenes in the Flash Vacuum Pyrolysis of Dibenzosuberones

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