17122-96-2

Usage

Chemical Family

Anthracene family

Type

Polycyclic aromatic hydrocarbon

Derivative

Anthracene with two chlorine atoms and one methyl group

Usage

Organic synthesis and chemical research

Application

Building block for new compounds

Potential Applications

Medicinal chemistry and fluorescent probe in biological imaging

Health Risks

Toxic and potentially carcinogenic properties

Environmental Risks

May pose environmental risks

Handling Precaution

Handle with caution due to health and environmental risks

Upstream product

• 50259-93-3 1,8-dichloro-9,10-dihydroanthracen-9-one 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 60624-80-8 1,8-dichloro-9-methyl-9,10-dihydro-[9]anthrol 
• 64-19-7 acetic acid 
• 917-54-4 methyllithium 
• 82-43-9 1,8-dichloroanthraquinone 

Downstream Products

• 100367-16-6 1,8-Bis-(2,3-dimethyl-phenyl)-9-methyl-anthracene 

Relevant academic research and scientific papers

Restricted Rotation Involving the Tetrahedral Carbon. LX. peri-Substituent Effect on the Rotational Barrier of the 9-Methyl Group in Several Trypticene Derivatives

Dynamic 1H NMR study was made on several 1-substituted 8,13-dichloro-9-methyltriptycenes and 8-chloro-13-fluoro-9-methyltriptycenes to examine the effect of peri-substituents on the rotational barrier of the 9-methyl group.The rotational barrier height increases in the expected order as the 1-hydrogen is repleaced by a bulkier group up to CH3, but shows a very low value when a t-butyl group is introduced into 1-position to show that destabilization of the ground state by the bulky t-butyl group exceeds that of the transition state for rotation.

1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head -to- Tail Photodimerisation

Several 1,8,10-functionalised anthracene derivatives and a couple of 1,8,9-functionalised anthracene analogous, bearing alkynyl substituents at positions 1 and 8 were synthesised and their photochemistry investigated in UV irradiation experiments. Almost all compounds could be converted into their 9,10:10′,9′- head -to- tail photodimers completely excluding the formation of the corresponding head -to- head isomers. Working under non-inert conditions led to formation of endoperoxides in some cases. Furthermore, a non-classical [4π+2π] photodimer was obtained from 1,8,10-tris[(trimethylsilyl)ethynyl]anthracene with one of the alkynyl substituents involved in the photoreaction. The 1 H and 13 C NMR spectra of all classical and non-classical photodimers were compared with those of the endoperoxides identifying characteristic shifts for the atoms at positions 9 and 10. Moreover, solid-state structures were determined for one or more of each representative.

Unsymmetrically Substituted 1,8-Diarylanthracenes

Unsymmetrically substituted 1,8-diarylanthracenes where the aryl rings are m-tolyl (5), o-tolyl (6), and 2,3-dimethylphenyl (7) have been synthesized; the barriers to aryl ring rotation in these hydrocarbons were found to be 5.3, 10.4, and 16.3 kcal/mol, respectively.Addition of either an acetoxyl (14) or a methyl (15) substituent at C-9 of the dixylylanthracene gave mixtures of cis and trans isomers that also exhibited rotation of an aryl ring within the temperature range 25-120 deg C.X-ray crystal structures for the cis- (14b) and trans- (14a) 9-acetoxydixylylanthracenes demonstrated significant distortion in the geometry of the anthracene ring, permitting rotation of the aryl rings with unexpected ease in solutions at temperatures above 100 deg C.