6408-78-2

Basic information

• Product Name: ACID BLUE 25
• Synonyms: Acid Blue 25 (C.I.);Acid Blue?5;sodium 1-amino-9,10-dioxo-4-phenylaminoanthracene-2-sulphonate;Alizarin saphirol A;Acid Green P-3B;2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-9,10-dioxo-4-(phenylamino)-, monosodium salt;alizarine saphirol A;ACID ANTHRACENE BLUE A
• CAS NO: 6408-78-2
• Molecular Formula: C₂₀H₁₃N₂O₅S*Na
• Molecular Weight: 416.38
• EINECS: 229-068-1
• Product Categories: Dyes and Pigments;Organics;A;Stains and Dyes;Stains&Dyes, A to
• Mol File: 6408-78-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: >300℃
• Boiling Point: 846.88℃[at 101 325 Pa]
• Appearance: Blue/Powder
• Density: 1.491[at 20℃]
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: DMSO (Slightly), Water (Slightly)
• Water Solubility: 2.79g/L at 20℃
• CAS DataBase Reference: ACID BLUE 25(CAS DataBase Reference)
• NIST Chemistry Reference: ACID BLUE 25(6408-78-2)
• EPA Substance Registry System: ACID BLUE 25(6408-78-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 6408-78-2(Hazardous Substances Data)

Usage

Uses

Acid Blue 25, is used for dyeing wool, silk and mixed fabric and printing them in a direct method.Dyes and metabolites.

Preparation

(a) 1-Amino-2,4-dibromoanthracene-9,10-dione?with aniline condensation, its product 1-amino-4- anilino-2-bromo-anthraquinone?in phenol in pressure with aqueous sodium sulfite, were hot. (b) the 1-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (sodium) in water medium copper salt as the catalyst used with aniline condensation.

Flammability and Explosibility

Nonflammable

Properties and Applications

blue. Blue powder. The little blue soluble in water, but soluble in acetone, ethanol, slightly soluble in benzene, four hydrogen naphthalene, insoluble in nitrobenzene and xylene. Meet strong sulfuric acid as dark, after diluted blue precipitation. Mainly used for dyeing nylon, polyamide for supporting the dye. Can also be used for wool, silk and blended fabric dyeing and printing directly. Can also be used in leather, electrical-controlled aluminum soap and color. Standard Light Fastness Soaping Persperation Fastness Oxygen bleaching Fastness to seawater Fading Stain Fading Stain Fading Stain ISO 5-6 3-4 4 3 3 AATCC 4-5 1-2 1-2 4 1-2 2

Standard

Light Fastness

Fading

Stain

ISO

5-6

AATCC

4-5

InChI:InChI=1/C20H14N2O5S.Na/c21-18-15(28(25,26)27)10-14(22-11-6-2-1-3-7-11)16-17(18)20(24)13-9-5-4-8-12(13)19(16)23;/h1-10,22H,21H2,(H,25,26,27);/q;+1/p-1

Synthetic route

sodium 1-amino-4-bromoanthraquinone-2-sulfonate (6258-06-6) + aniline (62-53-3) → acid blue 25 (6408-78-2)

Conditions	Yield
With copper In aq. phosphate buffer at 80℃; for 0.333333h; pH=6 - 7; Microwave irradiation;	90%
With disodium hydrogenphosphate; sodium dihydrogenphosphate; copper In water at 80℃; for 0.333333h; Microwave irradiation;	90%
With sodium carbonate; copper(II) sulfate In water at 90℃; for 48h; Ullmann coupling;	60%

sodium 1-amino-4-bromoanthraquinone-2-sulfonate (6258-06-6) + aniline (62-53-3) → sodium 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (25492-62-0) + acid blue 25 (6408-78-2)

Conditions	Yield
With disodium hydrogenphosphate; sodium dihydrogenphosphate; copper In water at 80℃; under 7500.75 Torr; for 0.0833333h; pH=6 - 7; Ullmann coupling reaction; microwave irradiation;	A n/a B 55%

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + aniline (62-53-3) → acid blue 25 (6408-78-2)

Conditions	Yield
With copper Ullmann reaction; aq. phosphate buffer; Microwave irradiation; Heating;

sodium cyanide (143-33-9) + acid blue 25 (6408-78-2) → 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2,3-dicarbonitrile (86397-45-7)

Conditions	Yield
With ammonium bicarbonate 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h;	96%

acid blue 25 (6408-78-2) → 1,4-diamino-9,10-anthraquinone (128-95-0)

Conditions	Yield
With hydrogenchloride; acetic acid; tin(ll) chloride for 3h; Heating;	89%

acid blue 25 (6408-78-2) → 4-phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (102160-11-2)

Conditions	Yield
Stage #1: acid blue 25 With hydrogenchloride; water; sodium nitrite at 0 - 20℃; Stage #2: With ethanol; zinc at 20℃; for 0.00833333h;	79%

ethanol (64-17-5) + 2'-benzyloxyacetophenone (31165-67-0) + acid blue 25 (6408-78-2) → C37H28N2O3 (698355-95-2)

Conditions	Yield
With potassium hydroxide for 2h; Heating / reflux;	32.7%

1-dodecyl alcohol (112-53-8) + acid blue 25 (6408-78-2) + sodium hydroxide → 1-amino-4-anilino-2-dodecyloxy-anthraquinone

Conditions	Yield
at 120℃;
at 120℃;

acid blue 25 (6408-78-2) → sodium salt of 1,4-diaminoanthraquinone-2-sulfonic acid (6471-06-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / acetic acid; SnCl2; HCl / 3 h / Heating 2: 51 percent / chlorosulfonic acid; Na2CO3 / nitrobenzene / 3 h / 130 °C View Scheme

acid blue 25 (6408-78-2) → 1-Amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracen-2-carbonitril (32571-82-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 0.08 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 2-amino-ethanol / 0.08 h / 160 °C View Scheme

acid blue 25 (6408-78-2) → 4-Amino-3-hydroxy-9,10-dioxo-1-phenylamino-9,10-dihydroanthracen-2-carbonitril

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 3.1 g / 30percent aq. NaOH / pyridine / 2 h / 100 °C View Scheme

acid blue 25 (6408-78-2) → 1-Amino-2-(Δ2-1,3-oxazolin-2-yl)-4-(phenylamino)anthrachinon

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 0.08 h / 160 °C 3: 3.1 g / 1,2-dichloro-benzene / 24 h / 160 °C View Scheme
Multi-step reaction with 3 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 0.08 h / 160 °C 3: 0.14 g / nitrobenzene / 24 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 0.15 g / 0.08 h / 160 °C View Scheme

acid blue 25 (6408-78-2) → 4-Amino-3-(2-hydroxyaethylamino)-9,10-dioxo-1-phenylamino-9,10-dihydroanthracen-2-carbonitril

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 0.16 g / 0.08 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 2 g / pyridine / 48 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 0.16 g / 2-amino-ethanol / 0.08 h / 160 °C View Scheme

acid blue 25 (6408-78-2) → 1-Amino-2-(benzimidazol-2'-yl)-4-(phenylamino)anthrachinon

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 0.08 h / 160 °C 3: 1.26 g / nitrobenzene / 24 h / 160 °C View Scheme
Multi-step reaction with 3 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 1.2 g / 2-amino-ethanol / 0.08 h / 160 °C 3: 1.26 g / nitrobenzene / 24 h / 160 °C View Scheme

acid blue 25 (6408-78-2) → 1-Amino-9,10-dioxo-4-phenylamino-2-(1'H-tetrazol-5'-yl)9,10-dihydroanthracen-3-carbonitril

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 4 g / NaN3, NH4Cl / dimethylformamide / 15 h / 80 °C View Scheme

acid blue 25 (6408-78-2) → 4-Amino-3-(3-(dimethylamino)propylamino)-9,10-dioxo-1-phenylamino-9,10-dihydroanthracen-2-carbonitril

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 1.) ammonium hydrogen carbonate / 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h 2: 2.8 g / 24 h / Ambient temperature View Scheme

acid blue 25 (6408-78-2) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → C29H17N2O6S(1-)*Na(1+) (1388148-81-9)

Conditions	Yield
With sodium carbonate In dimethyl sulfoxide; 1,2-dichloro-benzene at 170 - 172℃; for 4h;

acid blue 25 (6408-78-2) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → C29H14N2O15S4(4-)*4Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / 1,2-dichloro-benzene; dimethyl sulfoxide / 4 h / 170 - 172 °C 2.1: sulfur trioxide; sulfuric acid / 3 h / 85 - 90 °C 2.2: 1 h / 40 - 45 °C View Scheme

acid blue 25 (6408-78-2) → C20H11N3O5S*Na(1+)

Conditions	Yield
With sulfuric acid; acetic acid; sodium nitrite at 5 - 10℃;

Upstream product

• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 62-53-3 aniline 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 

Downstream Products

• 1388148-81-9 C₂₉H₁₇N₂O₆S^(1-)*Na⁽¹⁺⁾ 
• 102160-11-2 4-phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid 
• 698355-95-2 C₃₇H₂₈N₂O₃ 
• 32571-82-7 1-Amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracen-2-carbonitril 
• 6471-06-3 sodium salt of 1,4-diaminoanthraquinone-2-sulfonic acid 
• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 86397-45-7 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2,3-dicarbonitrile 

Relevant articles and documents

Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3

Ectonucleoside triphosphate diphosphohydrolases (NTPDases) catalyze the hydrolysis of nucleoside tri- and di-phosphates to mono-phosphates. The products are subsequently hydrolyzed by ecto-5′-nucleotidase (ecto-5′-NT) to nucleosides. NTPDase inhibitors have potential as novel drugs, e.g., for the treatment of inflammation, neurodegenerative diseases, and cancer. In this context, a series of anthraquinone derivatives structurally related to the anthraquinone dye reactive blue-2 (RB-2) was synthesized and evaluated as inhibitors of human NTPDases utilizing a malachite green assay. We identified several potent and selective inhibitors of human NTPDase2 and -3. Among the most potent NTPDase2 inhibitors were 1-amino-4-(9-phenanthrylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (20, PSB-16131, IC50 of 539 nM) and 1-amino-4-(3-chloro-4-phenylsulfanyl)phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (48, PSB-2020, IC50 of 551 nM). The most potent NTPDase3 inhibitors were 1-amino-4-[3-(4,6-dichlorotriazin-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (42, PSB-1011, IC50 of 390 nM) and 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (33, PSB-2046, IC50 of 723 nM). The best NTPDase2 inhibitor 20 showed a non-competitive inhibition type, while the NTPDase3 inhibitor 42 behaved as a mixed-type inhibitor. These potent compounds were found to be selective vs. other NTPDases. They will be useful tools for studying the roles of NTPDase2 and -3 in physiology and under pathological conditions.

Development of 1-Amino-4-(phenylamino)anthraquinone-2-sulfonate Sodium Derivatives as a New Class of Inhibitors of RANKL-Induced Osteoclastogenesis

A series of 1-amino-4-(phenylamino)anthraquinone-2-sulfonate sodium derivatives was synthesized and evaluated for osteoclast inhibition using a TRAP-staining assay. Among them, two compounds, LCCY-13 and LCCY-15, dose-dependently suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclast formation. Moreover, the cytotoxicity assay on RAW264.7 cells suggested that the inhibition of osteoclastic bone resorption by these compounds was not a result of their cytotoxicity. Further, the inhibitory activities of compounds LCCY-13 and LCCY-15 were further confirmed by including specific inhibition of NFATc1 expression levels in nuclei using an immunofluorescent analysis. In addition, LCCY-13 and LCCY-15 also significantly attenuated the bone resorption activity of osteoclasts according to a pit formation assay. Thus, a new class of 1-amino-4-(phenylamino)anthraquinone-2-sulfonate sodium compounds might be considered as an essential lead structure for the further development of anti-resorptive agents.

Erratum : Correction to anthraquinone derivatives as potent inhibitors of c-met kinase and the extracellular signaling pathway (ACS Medicinal Chemistry Letters (2013) 4 (408-403) DOI: 10.1021/ml4000047)

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