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4981-66-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 4981-66-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,9,8 and 1 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4981-66:
(6*4)+(5*9)+(4*8)+(3*1)+(2*6)+(1*6)=122
122 % 10 = 2
So 4981-66-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H10O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8,15-16H

4981-66-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name anthracene-9,10-diol

1.2 Other means of identification

Product number -
Other names 9,10-Anthracenediol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4981-66-2 SDS

4981-66-2Synthetic route

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

cyclopentadienyliron hexafluorophosphate of 9,10-dihydroanthracene

cyclopentadienyliron hexafluorophosphate of 9,10-dihydroanthracene

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
In N,N-dimethyl-formamide electrolysis in 0.2M KClO4 with mercury pool working electrode, Ag/0.1M AgNO3 reference electrode, Pt counter electrode, potential -1.95 V;88%
ethanol
64-17-5

ethanol

oxanthrone
549-99-5

oxanthrone

sodium acetate
127-09-3

sodium acetate

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

anthracene
120-12-7

anthracene

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
With lead dioxide; acetic acid anschl. mit NaOH;
oxanthrone
549-99-5

oxanthrone

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
With water Darst.;
ethanol
64-17-5

ethanol

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
Irradiation;
9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

phenylmagnesium bromide

phenylmagnesium bromide

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

9,10-diphenylanthracene
1499-10-1

9,10-diphenylanthracene

C

anthranol
6318-17-8

anthranol

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

A

9,10-dihydroanthracene
613-31-0

9,10-dihydroanthracene

B

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

C

anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

Conditions
ConditionsYield
Elektrochemische Reduktion;
oxanthrone
549-99-5

oxanthrone

acetic acid
64-19-7

acetic acid

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

oxanthrone
549-99-5

oxanthrone

toluene
108-88-3

toluene

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

anthracene
120-12-7

anthracene

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With 2-Picolinic acid; tert.-butylhydroperoxide; air; ferric nitrate In pyridine; acetic acid at 20℃; for 1h;A 0.38 mmol
B 0.87 mmol
With 2-Picolinic acid; tert.-butylhydroperoxide; ferric nitrate In pyridine; acetic acid at 20℃; for 1h; Product distribution; Mechanism; variation of reagents and reaction conditions;A 0.56 mmol
B 1.30 mmol
anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With perchloric acid; copper(II) ion In water; acetonitrile at 83℃; Rate constant;
1-Bromoanthraquinone
632-83-7

1-Bromoanthraquinone

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
In ethanol Quantum yield; Ambient temperature; Irradiation; different irradiation wavelengths, different products;
1,5-dibromo-9,10-anthraquinone
602-77-7

1,5-dibromo-9,10-anthraquinone

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
In ethanol Quantum yield; Ambient temperature; Irradiation; different irradiatione wavelengths, different product;
1,8-dibromoanthraquinone
38313-16-5

1,8-dibromoanthraquinone

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
In ethanol Quantum yield; Ambient temperature; Irradiation; different irradiation wavelengths, different products;
Dikalium-9,10-dihydroxyanthracendischwefelsaeureester
86370-22-1

Dikalium-9,10-dihydroxyanthracendischwefelsaeureester

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
In ethanol Quantum yield; Mechanism; Ambient temperature; Irradiation; deoxygenated solutions, E(excit.), further solvent and temp.;
tetralin
119-64-2

tetralin

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

A

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

B

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
at 295℃; Mechanism; other hydrogen donors and acceptors; kinetic isotope effects;
9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

9,10-dihydro-9,10-dihydroxyanthracene
58343-58-1

9,10-dihydro-9,10-dihydroxyanthracene

Conditions
ConditionsYield
With lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran at 15℃; for 1h; Product distribution;
With lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran at 15℃; for 1h; Yield given. Yields of byproduct given;
With triethylamine alane In tetrahydrofuran for 6h;
C19H18O4
113160-92-2

C19H18O4

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
In diphenylether at 200℃; Thermodynamic data; Rate constant; ΔH(excit.), ΔS(excit.);
ethanol
64-17-5

ethanol

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

hydrosulfite sodium

hydrosulfite sodium

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

ethanol
64-17-5

ethanol

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

platinum black

platinum black

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
Hydrogenation;
ethanol
64-17-5

ethanol

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

zinc dust

zinc dust

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

sulfuric acid
7664-93-9

sulfuric acid

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

aluminium-powder

aluminium-powder

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

aluminium alkoxide

aluminium alkoxide

A

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

B

anthracene
120-12-7

anthracene

C

cis-9,10-dihydroanthracene-9,10-diol
35058-16-3

cis-9,10-dihydroanthracene-9,10-diol

hydrogenchloride
7647-01-0

hydrogenchloride

oxanthrone
549-99-5

oxanthrone

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

oxanthrone
549-99-5

oxanthrone

water
7732-18-5

water

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

oxanthrone
549-99-5

oxanthrone

alcoholic alkali

alcoholic alkali

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester
1705-94-8

acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester

alkaline solution

alkaline solution

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

oxanthrone
549-99-5

oxanthrone

alkali

alkali

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

3-(triethoxypropyl) isocyanate
24801-88-5

3-(triethoxypropyl) isocyanate

C34H52N2O10Si2

C34H52N2O10Si2

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 65℃; for 20h;78%
1-thiopropane
107-03-9

1-thiopropane

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-bis(1-propylthio)anthracene

9,10-bis(1-propylthio)anthracene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 1h; Heating;77%
succinic acid anhydride
108-30-5

succinic acid anhydride

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-bis(2-carboxyethyl)carbonyloxyanthracene

9,10-bis(2-carboxyethyl)carbonyloxyanthracene

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 60℃; for 2h;65%
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

cyclohexane-1,2-dicarboxylic acid
1687-30-5

cyclohexane-1,2-dicarboxylic acid

9,10-bis(2-carboxycyclohexyl)carbonyloxyanthracene

9,10-bis(2-carboxycyclohexyl)carbonyloxyanthracene

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 60℃; for 2h; Inert atmosphere;58%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-bis(trimethylsilyloxy)anthracene
28871-52-5

9,10-bis(trimethylsilyloxy)anthracene

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 12h; Heating;49%
With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane for 8h;
3-chloromethyl-3-methyl oxetane
822-48-0

3-chloromethyl-3-methyl oxetane

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-bis((3-methyloxetan-3-yl)methyloxy)anthracene

9,10-bis((3-methyloxetan-3-yl)methyloxy)anthracene

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl acetamide; water at 60℃; for 5h; Inert atmosphere;45%
1-iodopropan-3-ol
627-32-7

1-iodopropan-3-ol

9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-bis(3-hydroxypropyloxy)anthracene
433718-08-2

9,10-bis(3-hydroxypropyloxy)anthracene

Conditions
ConditionsYield
Stage #1: 9,10-Dihydroxyanthracene With sodium hydroxide In dichloromethane for 0.166667h;
Stage #2: 1-iodopropan-3-ol In dichloromethane; water at 20℃; for 16h; Further stages.;
32%
at 20℃; for 12h;
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9-aminoanthracene
779-03-3

9-aminoanthracene

Conditions
ConditionsYield
With ammonium hydroxide at 150℃; under 18387.7 - 20594.2 Torr;
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With ethanol; platinum
With diethyl ether; platinum
With hydrogen iodide; acetic acid
With air In ethanol
With cobalt(III) phosphide In tetrahydrofuran-d8 at 20℃; for 24h; Catalytic behavior;
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

A

anthracen-9(10H)-one
90-44-8

anthracen-9(10H)-one

B

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With sulfuric acid
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

benzoyl chloride
98-88-4

benzoyl chloride

9,10-bis-benzoyloxy-anthracene
7437-71-0

9,10-bis-benzoyloxy-anthracene

Conditions
ConditionsYield
With alkali
9,10-Dihydroxyanthracene
4981-66-2

9,10-Dihydroxyanthracene

Dikalium-9,10-dihydroxyanthracendischwefelsaeureester
86370-22-1

Dikalium-9,10-dihydroxyanthracendischwefelsaeureester

Conditions
ConditionsYield
With pyridine; chlorosulfonic acid; potassium hydroxide 2.) H2O, pH=10; Yield given;

4981-66-2Relevant articles and documents

DNA-Triggered Enhancement of Singlet Oxygen Production by Pyridinium Alkynylanthracenes

Fudickar, Werner,Bauch, Marcel,Ihmels, Heiko,Linker, Torsten

, p. 13591 - 13604 (2021)

There is an ongoing interest in 1O2 sensitizers, whose activity is selectively controlled by their interaction with DNA. To this end, we synthesized three isomeric pyridinium alkynylanthracenes 2 o–p and a water-soluble trapping reagent for 1O2. In water and in the absence of DNA, these dyes show a poor efficiency to sensitize the photooxygenation of the trapping reagent as they decompose due to electron transfer processes. In contrast, in the presence of DNA 1O2 is generated from the excited DNA-bound ligand. The interactions of 2 o–p with DNA were investigated by thermal DNA melting studies, UV/vis and fluorescence spectroscopy, and linear and circular dichroism spectroscopy. Our studies revealed an intercalative binding with an orientation of the long pyridyl-alkynyl axis parallel to the main axis of the DNA base pairs. In the presence of poly(dA : dT), all three isomers show an enhanced formation of singlet oxygen, as indicated by the reaction of the latter with the trapping reagent. With green light irradiation of isomer 2 o in poly(dA : dT), the conversion rate of the trapping reagent is enhanced by a factor >10. The formation of 1O2 was confirmed by control experiments under anaerobic conditions, in deuterated solvents, or by addition of 1O2 quenchers. When bound to poly(dG : dC), the opposite effect was observed only for isomers 2 o and 2 m, namely the trapping reagent reacted significantly slower. Overall, we showed that pyridinium alkynylanthracenes are very useful intercalators, that exhibit an enhanced photochemical 1O2 generation in the DNA-bound state.

Radical-Pair Dynamics in the Photoreduction of Anthraquinone in Sodium Dodecyl Sulfate Micellar Solution Detected by Pulse-Mode Product-Yield-Detcted Electron Spin Resonance: Temperature and Salt Dependence

Polyakov, Nicolai E.,Okazaki, Masaharu,Konishi, Yoshinari,Toriyama, Kazumi

, p. 15108 - 15113 (1995)

The dynamical behavior of the radical pair (RP) produced in the photoreduction of anthraquinone in sodium dodecyl sulfate (SDS) micellar solutions has been observed at various temperatures and salt concentrations by using the pulse-mode product-yield-detected ESR (PYESR) technique.Trough the numerical calculation of the time-domain PYESR response by the Runge-Kutta method applied to a reaction scheme, dynamical parameters such as the escape rate of the RP (kESC) and the rate of spin trapping directly from the RP (kST) have been obtained.Since these kinetic parameters are very informative for elucidating the micelle dynamics, we may call this method the "spin-pair-probe" technique.

Luminescence of a new Ru(II) polypyridine complex controlled by a redox-responsive protonable anthra[1,10]phenanthrolinequinone

Hartl, Frantisek,Vernier, Sandrine,Belser, Peter

, p. 1891 - 1908 (2005)

Redox-controlled luminescence quenching is presented for a new Ru(II)-bipyridine complex [Ru(bpy)2(1)]2+ where ligand 1 is an anthra[1,10]phenanthrolinequinone. The complex emits from a short-lived metal-to-ligand charge transfer, 3MLCT state (τ = 5.5 ns in deaerated acetonitrile) with a low luminescence quantum yield (5 × 10 -4). The emission intensity becomes significantly enhanced when the switchable anthraquinone unit is reduced to corresponding hydroquinone. On the contrary, chemical one-electron reduction of the anthraquinone moiety to semiquinone in aprotic tetrahydrofuran results in total quenching of the emission.

PHOTOCHEMICAL REACTIONS OF CHLOROANTHRAQUINONES

Hamanoue, Kumao,Yokoyama, Kazuo,Miyake, Takao,Kasuya, Toshihiro,Nakayama, Toshihiro,Teranishi, Hiroshi

, p. 1967 - 1970 (1982)

Irradation of 1,5-dichloroanthraquionone (1,5-DCAQ) with 366 nm light in ethanol gives anthrahydroquinone (AQH2) as a final product.This is interpreted interms of the following cosecutive reactions; 1,5-DCAQ --hν--> 1,5-dichloroanthrahydroquinone --hν--> 1-chloroanthraquinone --hν--> 1-chloroanthrahydroquinone --hν--> anthraquinone --hν--> AQH2.Similar reactions were also observed for other α-chloroanthraquinones.

Th-symmetrical hexakisadducts of C60 with a densely packed π-donor shell can act as energy- or electron-transducing systems

Diekers, Michael,Luo, Chuping,Guldi, Dirk M.,Hirsch, Andreas

, p. 979 - 991 (2002)

For the first time several Th-symmetrical hexakisadducts of C60 bearing up to six electro- and photoactive o-phenylene diamine or 9,10-dialkoxyanthracene moieties were synthesized and subjected to photoinduced electron/energy-transfer studies. Both donors form a densely packed π-donor shell surrounding the fullerene core. In these novel core-shell ensembles (7 and 19), either an efficient energy transfer from the dialkoxyanthracene periphery, or an electron transfer from the o-phenylene diamine periphery transduces the flow of excited-state energy or electrons, respectively, to the fullerene moiety, which resides in the central core. Due to the relatively high reduction potential of the fullerene core, which is anodically shifted by ≈0.7 V, compared with that of pristine C60, the outcome of these intramolecular reactions depends mainly on the donor ability of the peripheral system. Interestingly, the charge-separated state in the o-phenylene diamine heptad (7; τ = 2380 ns in benzonitrile) is stabilized by a factor of 20 relative to the corresponding o-phenylene diamine dyad (6; τ = 120 ns in benzonitrile), an effect that points unequivocally to the optimized storage of charges in this highly functionalized fullerene ensemble.

Bolton et al.

, p. 465,469 (1962)

Intermediates in the cleavage of endoperoxides

Bauch, Marcel,Klaper, Matthias,Linker, Torsten

supporting information, (2017/03/24)

The decomposition of anthracene endoperoxides has been investigated under various conditions. Thermolyses proceed via radical intermediates and afford anthracenes and rearrangement products, depending on the substitution pattern. Interestingly, not only the O–O but also the C–O bond can be cleaved homolytically. Under basic conditions fragmentations take place, affording anthraquinone, and reactive oxygen species. This mechanism explains the often observed decomposition of endoperoxides during work-up. Finally, an acid-catalyzed cleavage has been observed under release of hydrogen peroxide. The results should be interesting for the mechanistic understanding of peroxide decomposition and the endoperoxides might serve as mild sources of reactive oxygen species for future applications. Copyright

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