853-68-9

Basic information

• Product Name: ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT
• Synonyms: sodiumanthraquinone-2,6(2,7)-disulfonate;Sodiumanthraquinone-2,6-disulfonate;ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT;DISODIUM ANTHRAQUINONE-2,6-DISULFONATE;2,6-ANTHRAQUINONEDISULFONIC ACID DISODIUM SALT;9,10-DIHYDRO-9,10-DIOXO-2,6-ANTHRACENEDISULFONIC ACID DISODIUM SALT;9,10-ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT;disodium 9,10-dihydro-9,10-dioxoanthracene-2,6-disulphonate
• CAS NO: 853-68-9
• Molecular Formula: C₁₄H₆O₈S₂*2Na
• Molecular Weight: 412.3
• EINECS: 212-719-9
• Product Categories: Anthraquinones;Anthraquinonesulfonic Acids
• Mol File: 853-68-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 325 °C
• Appearance: pink powder
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: H2O: 10 mg/mL, clear
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT(853-68-9)
• EPA Substance Registry System: ANTHRAQUINONE-2,6-DISULFONIC ACID DISODIUM SALT(853-68-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 853-68-9(Hazardous Substances Data)

Usage

Description

Anthraquinone-2,6-disulfonic acid disodium salt, also known as Disodium anthraquinone-2,6-disulfonate, is an anthraquinone compound characterized by its pink powder appearance. It is primarily used in proteomics research, where its unique chemical properties contribute to the study and analysis of proteins.

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