1,8-Dichloroanthracene-9,10-dione

1,8-Dichloroanthracene-9,10-dione

CAS Nr .: 82-43-9
Cov roj formula: C14H6Cl2O2
Molecular Luj: 277.1
SMILES Code: O=C1C2=C(C=CC=C2Cl)C(C3=CC=CC(Cl)=C13)=O

Khoom Taw qhia

Khoom npe

1,8-Dichloroanthracene-9,10-dione

CAS Nr

82-43-9

Molecular Formula

C14H6Cl2O2

Molecular Luj

277.1

SMILES Code

O{{0}C1C2=C(C=CC=C2Cl)C(C3=CC=CC(Cl)=C13)=O

MDL Nr.

PAB 000001191

 

Chemical Properties

 

Cov tshuaj no feem ntau tau txais los ntawm daj mus rau golden - daj crystalline hmoov nrog ib tug faint aromatic cim. Nws cov mis molecular yog C14H6Cl2O2, sib xws rau qhov hnyav molecular ntawm 277.10. Lub melting point feem ntau ntog nyob rau hauv thaj tsam ntawm 200-204 degree, qhia ib tug qhov dej-txhais crystalline lattice. Qhov ntsuas qhov ceev yog kwv yees li 1.58 g / cm³ nyob rau hauv ambient tej yam kev mob. Nws nthuav tawm me ntsis solubility hauv cov kuab tshuaj organic xws li acetic acid, nitrobenzene, thiab kub toluene, thaum qhia txog kev solubility hauv ethanol, diethyl ether, thiab xyaum tsis muaj solubility hauv dej. Cov molecule nta ib qho anthraquinone core nrog chlorine atoms hloov ntawm 1 thiab 8 txoj haujlwm. Cov quinone carbonyls thiab halogen substituents tsim ib qho hluav taws xob -tsis muaj ntxhiab tsw. Kev khaws cia rau hauv cov thawv kaw nruj nreem tiv thaiv los ntawm lub teeb ntawm qhov kub thiab txias yog feem ntau txaus, txawm hais tias desiccated tej yam kev mob raug pom zoo rau kev cia ntev. Kev sib cuag nrog cov muaj zog txo cov neeg ua haujlwm thiab cov hauv paus muaj zog yuav tsum zam.

 

Kev piav qhia

 

1,8-Dichloroanthracene-9,10-dione muaj cov txheej txheem tricyclic anthraquinone nrog cov tshuaj chlorine atom nyob rau ntawm 1 thiab 8 txoj haujlwm, uas yog peri rau cov pa roj carbonyl pawg. Cov tub ntxhais anthraquinone nta ob pawg carbonyl ntawm 9 thiab 10 txoj haujlwm, tsim kom muaj kev sib koom ua ke zoo heev, cov qauv txheej txheem nrog cov cim quinoid. Txoj kev sib raug zoo ntawm cov chlorine atoms thiab carbonyls tso cai rau muaj peev xwm intramolecular kev sib cuam tshuam uas cuam tshuam rau molecular conformation thiab hluav taws xob khoom. Cov hluav taws xob- rho tawm qhov xwm txheej ntawm ob qho tib si carbonyls thiab cov tshuaj chlorine atoms ua rau cov roj ntsha uas tsis muaj hluav taws xob, ua rau lawv muaj kev cuam tshuam rau nucleophilic nres. Qhov kev sib xyaw ua ke ntawm redox-active quinone core nrog halogen hloov pauv muab lub platform ntau yam rau kev ua haujlwm ntxiv los ntawm nucleophilic aromatic hloov pauv lossis kev sib txuas sib txuas. Lub compound sawv cev rau lub hauv paus tsev thaiv nyob rau hauv anthraquinone chemistry, qhov twg nws ua hauj lwm raws li ib tug precursor rau ntau complex derivatives nrog tailored zog.

 

Siv

 

Dye thiab Pigment Intermediate
Qhov no chlorinated anthraquinone ua haujlwm ua cov khoom siv tseem ceeb rau kev sib txuas ntawm vat dyes thiab disperse dyes. Cov chlorine atoms tuaj yeem hloov pauv los ntawm ntau yam nucleophiles xws li amines thiab phenoxides los qhia cov xim - hloov pauv hloov. Cov txiaj ntsig anthraquinone derivatives nthuav tawm zoo heev lightfastness thiab tinctorial zog, ua rau lawv muaj nuj nqis rau textile dyeing thiab luam ntawv daim ntaub ntawv. Keeb kwm, derivatives ntawm no compound tau siv los tsim xiav thiab violet dyes nrog superior ceev ceev zog.

 

Pharmaceutical Intermediate
Anthraquinone derivatives raug tshawb xyuas rau lawv cov haujlwm lom neeg, suav nrog tshuaj tua kab mob, tshuaj tua kab mob, thiab tshuaj tua kab mob. Cov tshuaj chlorine atoms nyob rau hauv cov compound no muab tes rau kev qhia cov pab pawg pharmacophoric los ntawm nucleophilic hloov pauv lossis ntoo khaub lig- kev sib txuas lus. Hloov kho anthraquinones tau pom tias muaj peev xwm ua DNA intercalators thiab topoisomerase inhibitors, nrog rau lub hom phiaj aromatic core enabling insertion ntawm DNA puag khub thiab cov neeg hloov pauv hloov affinity thiab selectivity.

 

Organic Electronic Khoom
Lub redox- nquag nquag thiab txuas ntxiv π-conjugation ntawm no anthraquinone derivative ua rau nws muaj txiaj ntsig rau kev tsim cov khoom siv hluav taws xob organic. Nws raug soj ntsuam raws li cov khoom siv cathode hauv lithium- ion roj teeb, qhov twg cov quinone moieties tau thim rov qab ob -electron txo. Cov hluav taws xob- rho chlorine atoms tuaj yeem kho qhov txo qis, cuam tshuam lub zog ceev thiab kev ruaj ntseg. Nws kuj tseem ua lub tsev thaiv rau cov organic semiconductors thiab them nqi -cov khoom thauj hauv cov organic teb- cuam tshuam cov transistors.

 

Synthetic Intermediate rau Functional Dyes
Tshaj li cov ntawv siv textile ib txwm siv, qhov sib xyaw no yog ua haujlwm hauv kev sib xyaw ua haujlwm ntawm cov dyes rau cov thev naus laus zis siab. Cov derivatives tau tshawb nrhiav los ua cov xim rau cov kua siv lead ua kua, xws li nyob ze -infrared absorbing dyes rau kho qhov muag cov ntaub ntawv, thiab raws li cov duab sensitizers hauv photodynamic kho. Cov tshuaj chlorine atoms ua kom muaj kev sib txuas ntxiv los ntawm palladium-catalyzed cross-coupling cov tshuaj tiv thaiv, tso cai rau kev qhia txog cov kab ke sib txuas uas txuas ntxiv kev nqus mus rau hauv thaj tsam ze -infrared.

 

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