853-68-9

Usage

Uses

Used in Proteomics Research:
Anthraquinone-2,6-disulfonic acid disodium salt is used as a research compound for proteomics, a branch of molecular biology that focuses on the large-scale study of proteins. Its chemical properties make it a valuable tool in this field, aiding in the identification, quantification, and characterization of proteins.

Purification Methods

Crystallise it three times from water, in the dark [Moore et al. J Chem Soc. Faraday Trans1 82 745 1986]. [Beilstein 11 IV 673.]

InChI:InChI=1/C14H8O8S2.2Na/c15-13-9-3-1-7(23(17,18)19)5-11(9)14(16)10-4-2-8(6-12(10)13)24(20,21)22;;/h1-6H,(H,17,18,19)(H,20,21,22);;/q;2*+1/p-2

Synthetic route

1,10-Phenanthroline (66-71-7) + cobalt(II) chloride hexahydrate + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → bis(2,6-anthraquinone disulfonate)tetrakis(1,10-phenanthroline)dicobalt(II)

Conditions	Yield
In water metal:S compd.:phen=1:1:2, stirred at room temp. for 5 min, heated at 160°C for 17 h; cooled to room temp., crysts. filtered, washed (water, acetone); elem. anal., TGA, powder XRD;	91%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + benzidine dihydrochloride (531-85-1) → C40H20N2O14S4(4-)*4Na(1+)

Conditions	Yield
In ethanol; water for 2h; Reflux;	82%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 9,10-dioxo-9,10-dihydro-2,6-anthracenedisulfonyl dichloride (36003-87-9)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 95℃; for 16h;	78%
With thionyl chloride; N,N-dimethyl-formamide 1.) reflux, 30 min, 2.) reflux, 2 h; Multistep reaction;
With phosphorus pentachloride at 180℃;
With thionyl chloride In N,N-dimethyl-formamide at -5 - 20℃; for 22h;

1,10-Phenanthroline (66-71-7) + manganese(II) chloride tetrahydrate + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + water (7732-18-5) → (2,6-anthraquinone disulfonate)bis(1,10-phenanthroline)aquamanganese(II) monohydrate

Conditions	Yield
In water metal:S compd.:phen=1:1:2, stirred at room temp. for 5 min, heated at 160°C for 17 h; cooled to room temp., crysts. filtered, washed (water, acetone); elem. anal., TGA, powder XRD;	76%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H6O8S2(2-)*Ca(2+)

Conditions	Yield
With calcium acetate In water; butan-1-ol at 170℃; for 72h; Autoclave;	70%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → Ba(2+)*C14H6O8S2(2-)

Conditions	Yield
With barium(II) acetate In water; butan-1-ol at 170℃; for 72h; Autoclave;	65%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H6O8S2(2-)*2H2O*Mg(2+)

Conditions	Yield
With water; magnesium acetate In butan-1-ol at 170℃; for 72h; Autoclave;	65%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H6O8S2(2-)*H2O*Sr(2+) (1276031-50-5)

Conditions	Yield
With water; strontium(II) acetate In butan-1-ol at 170℃; for 72h; Autoclave;	62%

[Cd(1,10-phenanthroline)2(NO3)2] (1184177-53-4, 128085-39-2, 399535-00-3, 725708-65-6) + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + water (7732-18-5) → [Cd2(1,10-phenanthroline)4(9,10-anthraquinone-2,6-disulfonate)2(H2O)1.5]

Conditions	Yield
In water High Pressure; aq. soln. was sealed in vessel, heated to 433 K in oven and kept for twodays, then slowly cooled to room temp.; ppt. was filtered, washed with water and EtOH, dried in vac.; elem. anal.;	54%

1,10-Phenanthroline (66-71-7) + copper(II) choride dihydrate + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + water (7732-18-5) → [Cu(anthraquinone-2,6-disulfonate)(1,10-phenanthroline)(H2O)3]*4H2O

Conditions	Yield
In water High Pressure; mixt. of anthraquinone deriv., phen and CuCl2*2H2O in water sealed into PTFE-lined stainless steel container, under autogeneous pressure, heatedat 140°C for 3 d, cooled to 20°C at 5°C/h; collected by filtration, washed with H2O and EtOH, dried at room temp.; elem. anal.;	48%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → anthracene-2,6-disulfonic acid dipotassium salt (66601-74-9)

Conditions	Yield
Stage #1: disodium 9,10-anthraquinone-2,6-disulfonate With ammonium carbonate In water at 80℃; Stage #2: With hydrogenchloride; zinc In water at 80℃; for 72h; Further stages;	48%

[2,2]bipyridinyl (366-18-7) + zinc diacetate (557-34-6) + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + water (7732-18-5) → [Zn(anthraquinone-2,6-disulfonate)(2,2'-bipyridine)(H2O)]*2H2O

Conditions	Yield
In water High Pressure; mixt. of anthraquinone deriv., 2,2'-bipy and Zn acetate in water sealed into PTFE-lined stainless steel container, under autogeneous pressure, heated at 170°C for 4 d, cooled to 20°C at 5°C/h; elem. anal.;	43%

[2,2]bipyridinyl (366-18-7) + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + water (7732-18-5) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → [Mn(anthraquinone-2,6-disulfonate)(2,2'-bipyridine)(H2O)]*2H2O

Conditions	Yield
In water High Pressure; mixt. of anthraquinone deriv., 2,2'-bipy and Mn acetate in water sealed into PTFE-lined stainless steel container, under autogeneous pressure, heated at 170°C for 4 d, cooled to 20°C at 5°C/h; elem. anal.;	36%

copper(II) choride dihydrate + disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) + 1,2-bis(imidazole-1-ylmethyl)benzene (42032-51-9) → 2C14H14N4*C14H6O8S2(2-)*Cu(2+)*H2O

Conditions	Yield
In water at 120℃; for 96h; Autoclave;	36%

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 2,6-dichloro-9,10-anthraquinone (605-40-3)

Conditions	Yield
With hydrogenchloride; sulfuric acid; sodium perchlorate In water at 100℃; for 336h;	28%
With hydrogenchloride; sodium chlorate

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H8O8S2(2-)*2Na(1+) (35199-34-9, 63118-37-6)

Conditions	Yield
With benzo[c][1,2,5]thiadiazole-4,7-dicarbonitrile; ethylenediaminetetraacetic acid; sodium acetate; cetyltrimethylammonim bromide; acetic acid In water Irradiation; pH=5.5;

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 9,10-anthraquinol-2,6-disodium sulphonate cation radical

Conditions	Yield
With trifluorormethanesulfonic acid at 40.9℃; Irradiation;

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H4Br2O8S2(2-)*2Na(1+) + C14H4Br2O8S2(2-)*2Na(1+) + C14H2Br4O8S2(2-)*2Na(1+)

Conditions	Yield
With sulfuric acid; bromine; nitric acid at 80℃; for 2h; Title compound not separated from byproducts;

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H8O8S2(3-)*2Na(1+) + sulfite radical anion

Conditions	Yield
With sodium sulfite In water Product distribution; Ambient temperature; Irradiation; photoreduction; reaction in the presence of Aerosol OT reverse micelles;

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → N,N'-bis<4-butyl>-2,6-anthraquinonedisulfonamide (158331-41-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / phosphoryl chloride, phosphorus pentachloride / 16 h / 95 °C 2: 78 percent / Et3N / dimethylformamide; CH2Cl2 / 40 h / Ambient temperature View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → N,N'-bis(4-aminobutyl)-2,6-anthraquinonedisulfonamide dihydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / phosphoryl chloride, phosphorus pentachloride / 16 h / 95 °C 2: 78 percent / Et3N / dimethylformamide; CH2Cl2 / 40 h / Ambient temperature 3: 75 percent / HCl gas / dimethylformamide View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 2,6-dichloroanthracene (26154-35-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaClO3, HCl 2: Al cyclohexoxide / various solvent(s) View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; sulfuric acid; sodium perchlorate / water / 336 h / 100 °C 2: aluminium; mercury dichloride / tetrachloromethane; cyclohexanol / 48 h / Reflux View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 9-bromo-2,6-dichloroanthracene (88847-74-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaClO3, HCl 2: Al cyclohexoxide / various solvent(s) 3: CuBr / chlorobenzene View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → bis(2,6-dichloro-9-triptycyl)methane

Conditions	Yield
Multi-step reaction with 4 steps 1: NaClO3, HCl 2: Al cyclohexoxide / various solvent(s) 3: CuBr / chlorobenzene 4: stable conformers View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → bis(2,6-dichloro-9-triptycyl)methane

Conditions	Yield
Multi-step reaction with 4 steps 1: NaClO3, HCl 2: Al cyclohexoxide / various solvent(s) 3: CuBr / chlorobenzene 4: stable conformers View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → 2,6-dichloro-9,10-dihydroanthracene (216107-59-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sulfuric acid; sodium perchlorate / water / 336 h / 100 °C 2: phosphorus; hydrogen iodide; iodine / 140 °C / Sealed ampoule View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → C14H6(2)H4Cl2

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; sulfuric acid; sodium perchlorate / water / 336 h / 100 °C 2: phosphorus; hydrogen iodide; iodine / 140 °C / Sealed ampoule 3: sodium / Reflux View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → S,S-anthracene-2,6-diyl di-thioacetate (1155232-20-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium carbonate / water / 80 °C 1.2: 72 h / 80 °C 2.1: phosphorus pentachloride / 120 °C 3.1: hydrogenchloride; tin(II) chloride dihdyrate / 90 °C View Scheme

disodium 9,10-anthraquinone-2,6-disulfonate (853-68-9) → anthracene-2,6-di(sulfonylchloride) (17408-01-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ammonium carbonate / water / 80 °C 1.2: 72 h / 80 °C 2.1: phosphorus pentachloride / 120 °C View Scheme

Downstream Products

• 26154-35-8 2,6-Dichlor-anthracen 
• 605-40-3 2,6-dichloro-9,10-anthraquinone