17135-78-3

Basic information

• Product Name: 2-Chloroanthracene
• Synonyms: 2-CHLOROANTHRACENE;BETA-CHLORO ANTHRACENE;2-chloro-anthracen;2-Chloroanthracene,95%
• CAS NO: 17135-78-3
• Molecular Formula: C₁₄H₉Cl
• Molecular Weight: 212.67
• Product Categories: Electronic Chemicals;Anthracenes;Aryl;C13 to C37+;Halogenated Hydrocarbons;Building Blocks;C13 to C37+;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 17135-78-3.mol

Chemical Properties

• Melting Point: 221-223 °C(lit.)
• Boiling Point: 275.35°C (rough estimate)
• Flash Point: 179.2 °C
• Appearance: beige to brown-beige powder or flakes
• Density: 1.1779 (rough estimate)
• Vapor Pressure: 2.42E-05mmHg at 25°C
• Refractive Index: 1.6012 (estimate)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2-Chloroanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroanthracene(17135-78-3)
• EPA Substance Registry System: 2-Chloroanthracene(17135-78-3)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• RTECS: CA9560000
• Hazardous Substances Data: 17135-78-3(Hazardous Substances Data)

Usage

Uses

Used in Environmental Research:
2-Chloroanthracene is used as a model compound for investigating the formation of polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs) in fly ash. This application is crucial for understanding the environmental impact and potential health risks associated with these toxic substances.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-Chloroanthracene serves as a key intermediate in the synthesis of polyfluorenes with anthraquinone or naphtylimide end caps. These synthesized materials have potential applications in various industries, such as electronics and pharmaceuticals, due to their unique properties and structures.

InChI:InChI=1/C14H9Cl/c15-14-6-5-12-7-10-3-1-2-4-11(10)8-13(12)9-14/h1-9H

Upstream product

• 131-09-9 2-chloroanthracene-9,10-dione 
• 1321539-25-6 2-(4-chlorobenzyl)benzaldehyde 
• 591-50-4 iodobenzene 
• 40137-29-9 2-methyl-4-chlorobenzaldehyde 
• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 
• 108-90-7 chlorobenzene 
• 1292302-63-6 C₁₄H₁₁ClO 
• 84-45-7 2,3-dichloro-anthraquinone 
• 7758-99-8 copper(II) sulfate 
• 7664-41-7 ammonia 
• 4887-99-4 2-chloroanthrone 
• 16331-51-4 Anthracene-2-carboxylic acid chloride 
• 98-46-4 3-trifluoromethylnitrobenzene 

Downstream Products

• 131-09-9 2-chloroanthracene-9,10-dione 
• 1981-38-0 2-phenylanthracene 
• 120-12-7 anthracene 
• 52251-71-5 2-ethylanthracene 
• 929103-27-5 2,2 '-(2-phenylanthracene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 929103-26-4 9,10-dibromo-2-phenylanthracene 
• 676578-20-4 2-(anthracene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1137660-99-1 2-phenylselenylanthracene 
• 189882-97-1 2-phenylthioanthracene 
• 613-12-7 2-methylanthracene 
• 17604-23-8 2-Chloro-11,12-cis-dichloro-9,10-dihydro-9,10-ethanoanthracen 

Relevant articles and documents

Cascade reaction for the synthesis of polycyclic aromatic hydrocarbons via transient directing group strategy

A Pd(II)-catalyzed cascade synthesis of diverse polycyclic aromatic hydrocarbons via transient directing group strategy has been developed, involving the consecutive arylation, cyclization and aromatization. The efficiency and practicality were demonstrated by wide substrate range, concise synthetic pathway and mild reaction conditions. The subsequent transformations of the benz[a]anthracene core accessed natural bioactive PAH molecules.

Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation

2-Anthrylethylene derivatives 1 E-5 E and 1 Z are synthesized to study the cis-trans photoisomerization. Interestingly, unlike 9-anthrylethylene derivatives, 2-anthrylethylene derivatives 1 E to 5 E do not exhibit E(trans) to Z (cis) photoisomerization upon direct and triplet sensitization. One-way Z (cis) to E (trans) photoisomerization of 1 Z is found to be very efficient under direct and triplet sensitization conditions, demonstrating the involvement of both singlet and triplet states. 1 E-5 E exhibits excitation wavelength dependent fluorescence indicating the existence of conformers (rotamers) at room temperature, which is confirmed by fluorescence lifetimes measurements of compounds 1 E and 2 E. Theoretical studies are carried out at DFT and ab initio methodology and the calculated relative energy difference of the conformers is very small; it ranges between 2.9 kJ·mol-1 to 6.3 kJ·mol-1 for both ground and excited states.

Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration

Polycyclic aromatic compounds can be synthesized from 2-benzylic- or 2-allylbenzaldehydes using a catalytic amount of In(III) or Re(I) complexes. By using this method, polycyclic aza-aromatic compounds can also be prepared efficiently. In these reactions, only water is formed as a side product.

Efficient synthesis of 9-tosylaminofluorene derivatives by boron trifluoride etherate-catalyzed aza-friedel-crafts reaction of in situ generated N-tosylbenzaldimines

An efficient and expeditious boron trifluoride etherate (BF 3·Et2O) catalyzed one-pot reaction for the synthesis of N-tosyl-9-aminofluorenes and anthracene derivatives from in situ generated N-tosylbenzaldimines via an aza-Friedal-Crafts reaction has been developed. The catalytic reaction shows high substrate tolerance with excellent yields.

A new InCl3-catalyzed reduction of anthrones and anthraquinones by using aluminum powder in aqueous media

InCl3-catalyzed reduction of anthrones and anthraquinones was investigated under different conditions. A new synthetic method for anthracenes in aqueous media under mild conditions is described.

Electron and oxygen transfer in polyoxometalate, H5PV2Mo10O40, catalyzed oxidation of aromatic and alkyl aromatic compounds: Evidence for aerobic Mars-van Krevelen-type reactions in the liquid homogeneous phase

The mechanism of aerobic oxidation of aromatic and alkyl aromatic compounds using anthracene and xanthene, respectively, as a model compound was investigated using a phosphovanadomolybdate polyoxometalate, H5PV2Mo10O40, as catalyst under mild, liquid-phase conditions: The polyoxometalate is a soluble analogue of insoluble mixed-metal oxides often used for high-temperature gas-phase heterogeneous oxidation which proceed by a Mars-van Krevelen mechanism. The general purpose of the present investigation was to prove that a Mars-van Krevelen mechanism is possible also in liquid-phase, homogeneous oxidation reactions. First, the oxygen transfer from H5PV2Mo10O40 to the hydrocarbons was studied using various techniques to show that commonly observed liquid-phase oxidation mechanisms, autoxidation, and oxidative nucleophilic substitution were not occurring in this case. Techniques used included (a) use of 18O-labeled molecular oxygen, polyoxometalate, and water; (b) carrying out reactions under anaerobic conditions; (c) performing the reaction with an alternative nucleophile (acetate) or under anhydrous conditions; and (d) determination of the reaction stoichiometry. All of the experiments pointed against autoxidation and oxidative nucleophilic substitution and toward a Mars-van Krevelen mechanism. Second, the mode of activation of the hydrocarbon was determined to be by electron transfer, as opposed to hydrogen atom transfer from the hydrocarbon to the polyoxometalate. Kinetic studies showed that an outer-sphere electron transfer was probable with formation of a donor-acceptor complex. Further studies enabled the isolation and observation of intermediates by ESR and NMR spectroscopy. For anthracene, the immediate result of electron transfer, that is formation of an anthracene radical cation and reduced polyoxometalate, was observed by ESR spectroscopy. The ESR spectrum, together with kinetics experiments, including kinetic isotope experiments and 1H NMR, support a Mars-van Krevelen mechanism in which the rate-determining step is the oxygen-transfer reaction between the polyoxometalate and the intermediate radical cation. Anthraquinone is the only observable reaction product. For xanthene, the radical cation could not be observed. Instead, the initial radical cation undergoes fast additional proton and electron transfer (or hydrogen atom transfer) to yield a stable benzylic cation observable by 1H NMR. Again, kinetics experiments support the notion of an oxygen-transfer rate-determining step between the xanthenyl cation and the polyoxometalate, with formation of xanthen-9-one as the only product. Schemes summarizing the proposed reaction mechanisms are presented.

METHANOANTHRACENEYL METHYL PIPERIDINYL COMPOUNDS

Compounds of formula I or I', STR1 wherein X and Y are independently selected from hydrogen, halo, and (1-6C)alkoxy;R 1 is selected from(A) (1-6C)alkyl; (B) phenyl and naphthyl or substituted versions thereof; (C) phenyl (1-3C)alkyl and naphthyl (1-3C) alkyl;(D) five-and six-membered heteroaryl rings;(E) heteroaryl (1-3C) alkyl and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disorders such as psychoses; pharmaceutical compositions comprising a compound of formula I or I' and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropsychiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I or I', or a pharmaceutically acceptable salt thereof are claimed. The invention also relates to novel processes for producing enantiomeric methanoanthracenyl sulfoxides.

Methanoanthrancenyl piperidyl antipsychotics

Compounds of formula I STR1 wherein X and Y are H or halo; R 2 is: [structures Ia, Ib or Ic;] STR2 R 3 is selected from unsubstituted or substituted alkyl, aryl or heteroaryl groups;R 4 is selected from H or (Cl-6)alkyl,and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disoders such as psychoses; pharmaceutical compositions comprising a compound of formula I and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropschiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof.

Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes

The determination of electron transfer equilibria A(1-) + B = A + B(1-) in the gas phase, with a pulsed-electron high-pressure mass spectrometer, leads to ΔG10, ΔH10, and ΔS10 values.These can be converted into the free energy, enthalpy and entropy changes, ΔGa0(B), ΔHa0(B) and ΔSa0(B), for the reaction e + B = B(1-), since the corresponding values for the reference compounds A are known.Results were obtained for 18 substituted naphthalenes, anthracene and substituted anthracenes.The results are compared with some theoretical predictions and the corresponding reduction potentials in solution.Rate constants for 13 exoergic electron-transfer reactions were also measured.These were found to be close to the ADO collision rates.

Piperidine derivatives, compositions and use

Compounds of formula I, Ia or Ib and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disorders such as psychoses; pharmaceutical compositions comprising a compound of formula I and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropschiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof; STR1