131-14-6

Basic information

• Product Name: 2,6-Diaminoanthraquinone
• Synonyms: 2,6-DIAMINOANTHRAQUINONE;2,6-ANTHRAQUINONYLDIAMINE;10-Anthracenedione,2,6-diamino-9;2,6-diamino-10-anthracenedione;2,6-Diamino-9,10-anthracenedione;2,6-diamino-9,10-anthraquinone;2,6-diaminoanthrachinon;2,6-diamino-anthraquinon
• CAS NO: 131-14-6
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.24
• EINECS: 205-013-7
• Product Categories: Intermediates of Dyes and Pigments;Aminoanthraquinones;Anthraquinones;C13 to C14;Carbonyl Compounds;Ketones;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 131-14-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: >325 °C(lit.)
• Boiling Point: 380.84°C (rough estimate)
• Flash Point: 287.6 °C
• Appearance: solid
• Density: 1.1907 (rough estimate)
• Vapor Pressure: 3.17E-12mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: insoluble in Chloroform
• PKA: 1.32±0.20(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,6-Diaminoanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diaminoanthraquinone(131-14-6)
• EPA Substance Registry System: 2,6-Diaminoanthraquinone(131-14-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CB6450000
• Hazardous Substances Data: 131-14-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

Safety Profile

An eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise it from pyridine or nitrobenzene (red needles). Column-chromatography on Al2O3/toluene is used to remove a fluorescent impurity, then it is recrystallised from EtOH. [Beilstein 14 H 215, 14 I 471, 14 II 120, 14 III 480, 14 IV 486.]

InChI:InChI=1/C14H10N2O2/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6H,15-16H2

Synthetic route

piperidine (110-89-4) + pyridine (110-86-1) + 1,1'-(9,10-dioxo-9,10-dihydro-anthracene-2,6-diyl)-bis-pyridinium; dichloride → 2,6-diamino-9,10-anthraquinone (131-14-6)

2,6-dichloro-9,10-anthraquinone (605-40-3) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With copper(I) sulfate; ammonia; copper(II) sulfate at 200℃;

Anthraquinone-2,6-disulfonic acid (84-50-4) + ammonium hydroxide → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
at 190℃; gibt zuerst 6-Amino-anthrachinon-sulfonsaeure-(2);
das Umwandlung verlaeuft mit besserer Ausbeute, wenn man dem Reaktionsgemisch Kupfersulfat zusetzt;

2,6-dichloro-9,10-anthraquinone (605-40-3) + ammonia (7664-41-7) + copper(II) sulfate (7758-99-8) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
at 200℃;

9,10-dichloroanthracene (605-48-1) + sulfuric acid (7664-93-9) → 2,7-diaminoanthraquinone (605-44-7) + 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
Erhitzen des Reaktionsgemischs mit Ammoniak und Braunstein auf 180grad;

2.6-dipyridinio-anthraquinone dichloride → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With piperidine; pyridine

ammonium salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With sodium chlorate; ammonium hydroxide

sodium-salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With ammonium hydroxide; potassium chlorate; ammonium nitrite
With ammonium hydroxide; sodium hydrogen arsenate

sodium-salt of/the/ 6-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With ammonia

sodium salt of/the/ anthraquinone-disulfonic acid-(2.6) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With ammonium hydroxide; copper(I) sulfate; copper(II) sulfate
With ammonium hydroxide; barium(II) chloride
With ammonium hydroxide at 190℃; im geschlossenen Rohr;

2,6-dibromoanthraquinone (633-70-5) → 2,6-diamino-9,10-anthraquinone (131-14-6)

Conditions	Yield
With ammonium hydroxide; copper(l) iodide

2,6-diamino-9,10-anthraquinone (131-14-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 2,6-bis(4-chlorobutyramido)anthracene-9,10-dione (134916-10-2)

Conditions	Yield
With pyridine for 4h; Heating;	100%

2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-diaminoanthracen-9(10H)-one (87120-50-1)

Conditions	Yield
With tin; water; sodium hydroxide In ethanol for 24h; Inert atmosphere; Reflux;	100%

2,6-diamino-9,10-anthraquinone (131-14-6) + Hexanoyl chloride (142-61-0) → N,N′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)dihexanamide (1335230-34-6)

Conditions	Yield
With pyridine In dichloromethane for 3h;	100%
With pyridine In dichloromethane at 27℃; for 3h; Inert atmosphere;	93%

2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-dibromoanthraquinone (633-70-5)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃;	98.4%
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 70℃; for 4h; Inert atmosphere;	98%
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 90℃; for 24h; Inert atmosphere;	97%

tert.-butylnitrite (540-80-7) + Cu(II)Br + 2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-dibromoanthraquinone (633-70-5)

Conditions	Yield
With hydrogenchloride	98.4%

3-hydroxy-2-naphthoyl chloride (1734-00-5) + 2,6-diamino-9,10-anthraquinone (131-14-6) → C36H22N2O6

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 10 - 20℃; for 2h;	97.8%
In 1-methyl-pyrrolidin-2-one at 10 - 20℃; for 2h;

2,6-diamino-9,10-anthraquinone (131-14-6) + 2-chloropropionyl chloride (625-36-5) → 2,6-bis(3-chloropropionamido)anthracene-9,10-dione (72966-79-1)

Conditions	Yield
for 5h; Heating;	95%
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	90%

2,6-diamino-9,10-anthraquinone (131-14-6) + 9H-fluoren-9-ylmethyl N-(3-chloro-3-oxo-propyl)carbamate (183720-79-8) → 2,6-bis-[N-(3-Fmoc-amino)-propionamide]anthracene-9,10-dione (1007890-01-8)

Conditions	Yield
In tetrahydrofuran for 7h; Heating;	95%
In tetrahydrofuran for 7h; Reflux;	95%
In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;

2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-diamino-9,10-dihydroanthracene (129032-19-5)

Conditions	Yield
With ammonium hydroxide; zinc at 90℃; for 64h;	94%
With ammonium hydroxide; zinc at 90℃; for 64h; Reduction;	94%
With hydrogenchloride; ammonium hydroxide; zinc In water at 100℃; for 23h; Sealed tube;	88%
With ammonium hydroxide; zinc In water at 90℃; for 72h;

2,6-diamino-9,10-anthraquinone (131-14-6) + 9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate (103321-49-9) → 2,6-bis-[N-(2-Fmoc-amino)-acetamide]anthracene-9,10-dione (1060669-72-8)

Conditions	Yield
In tetrahydrofuran for 7h; Reflux;	94%
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	88%
In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;

2,6-diamino-9,10-anthraquinone (131-14-6) + chloroacetyl chloride (79-04-9) → N,N’-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-chloroacetamide) (55077-07-1)

Conditions	Yield
for 3h; Heating;	91%
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	90%
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 24h;	90%

2,6-diamino-9,10-anthraquinone (131-14-6) → anthracene-2,6-diamine (46710-42-3)

Conditions	Yield
With sodium tetrahydroborate In isopropyl alcohol at 80℃; for 12h;	90%
With ammonium hydroxide; zinc
Multi-step reaction with 2 steps 1: tin; water; sodium hydroxide / ethanol / 24 h / Inert atmosphere; Reflux 2: sodium tetrahydroborate; sodium hydroxide / ethanol; water / 6 h / Reflux View Scheme

2-chloropropionyl chloride (7623-09-8) + 2,6-diamino-9,10-anthraquinone (131-14-6) → C20H16Cl2N2O4 (62799-41-1)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	90%

2,6-diamino-9,10-anthraquinone (131-14-6) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C34H20N6O10S2(2-)*2Na(1+)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 20 - 40℃; for 0.666667h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid at 5 - 10℃; pH=0.5 - 1;	90%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 40℃; for 0.5h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide at 5 - 10℃; pH=0.5 - 1;

2,6-diamino-9,10-anthraquinone (131-14-6) + methyl iodide (74-88-4) → 2,6-bis(dimethylamino)-9,10-anthraquinone (106580-21-6)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: methyl iodide In dimethyl sulfoxide at 20℃; for 0.166667h;	87%

2,6-diamino-9,10-anthraquinone (131-14-6) + Chloroacetic anhydride (541-88-8) → N,N’-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-chloroacetamide) (55077-07-1)

Conditions	Yield
With pyridine In nitrobenzene for 3h; Heating;	83%

2,6-diamino-9,10-anthraquinone (131-14-6) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 2,6-bis-(dimethylamino-methylene-imino)-anthraquinone

Conditions	Yield
In pyridine	83%

2,6-diamino-9,10-anthraquinone (131-14-6) + o-chlorobenzoyl chloride (609-65-4) → C28H16Cl2N2O4 (882864-41-7)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	80%

2,6-diamino-9,10-anthraquinone (131-14-6) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C34H20N6O10S2(2-)*2Na(1+)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 20 - 40℃; for 0.666667h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid at 0 - 5℃; pH=8 - 9;	80%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 40℃; for 0.5h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide at 0 - 5℃; pH=8 - 9;

2,6-diamino-9,10-anthraquinone (131-14-6) → 3,7-diamino-9,10-anthraquinone-2,6-disulfonic acid

Conditions	Yield
With sulfuric acid; dihydrogen peroxide at 100℃; for 5h; Cooling with ice;	80%

Phosphoroxy chloride + 2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-bis-(dimethylamino-methylene-imino)-anthraquinone

Conditions	Yield
In N-methyl-acetamide; dichloromethane; water	79%

2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-bis-(1-methylpyrrolidone-2-imino)-anthraquinone

Conditions	Yield
With ammonia; trichlorophosphate In 1-methylpyrrolidone-2-(N-methyl-butyrolactam); dichloromethane; water	78%

pyridine-2-carbaldehyde (1121-60-4) + iron(II) triflate + 2,6-diamino-9,10-anthraquinone (131-14-6) + water (7732-18-5) + acetonitrile (75-05-8) → C156H96Fe4N24O12(8+)*2C2H3N*H2O*8CF3O3S(1-)

Conditions	Yield
Reflux;	78%

Ni[H2CNCHC2(CH3)(OCH3)C(CH3)NCH2]2(2+)*2PF6(1-)=Ni[H2CNCHC2(CH3)(OCH3)C(CH3)NCH2]2(PF6)2 (74465-80-8) + 2,6-diamino-9,10-anthraquinone (131-14-6) → Ni[H2CNCHC2(CH3)(NHC14H6O2NH2)C(CH3)NCH2][H2CNCHC2(CH3)(OCH3)C(CH3)NCH2](2+)*2(PF6)(1-)=Ni(C17H25N4O(C14H9N2O2))(PF6)2

Conditions	Yield
In acetonitrile Ni-complex dissolved in acetonitrile, triethylamine, excess 1,6-diamineanthraquinone dissolved in acetonitrile added, soln. concd., refrigerated; crystals filtered off, washed with abs. methanol, vac.-dried, recrystd. in 1:1 acetonitrile-methanol, elem. anal.;	77.8%

2,6-diamino-9,10-anthraquinone (131-14-6) + benzoyl chloride (98-88-4) → 2,6-bis-benzoylamino-anthraquinone (6470-90-2)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃; for 24h;	75%
With 2,3-Dimethylaniline

dilitium phthalocyanine + 2,6-diamino-9,10-anthraquinone (131-14-6) → C14H10N2O2*C32H16N8(2-)*2Li(1+)

Conditions	Yield
In methanol for 72h; Reflux;	75%

2,6-diamino-9,10-anthraquinone (131-14-6) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 2,6-diamino-9,10-[di-(2,4-dinitrophenyl)hydrazono]-9H,10H-anthracene

Conditions	Yield
With phosphoric acid In ethanol for 24h; Heating;	70%

pyridine-2-carbaldehyde (1121-60-4) + nickel(II) tetrafluoroborate hexahydrate + 2,6-diamino-9,10-anthraquinone (131-14-6) + acetonitrile (75-05-8) → C156H96N24Ni4O12(8+)*8BF4(1-)*2C2H3N*2H2O

Conditions	Yield
Reflux;	67%

2,6-diamino-9,10-anthraquinone (131-14-6) → 2,6-diiodoanthracene-9,10-dione (78507-46-7)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With hydrogenchloride; sodium nitrite In water; acetonitrile at 0℃; for 0.5h; Stage #2: With potassium iodide In water; acetonitrile at 0 - 60℃; for 2h; Further stages.;	65%
Stage #1: 2,6-diamino-9,10-anthraquinone With hydrogenchloride; sodium nitrite In water; acetonitrile at 0℃; for 0.5h; Sandmeyer Reaction; Stage #2: With potassium iodide In water; acetonitrile at 20 - 60℃; for 2h;	63%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid; sodium nitrite at 0℃; Stage #2: With potassium iodide at 20℃; Sandmeyer reaction; Further stages.;	45%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid for 0.166667h; Inert atmosphere; Stage #2: With sodium nitrite In water at 0℃; for 3.5h; Inert atmosphere; Stage #3: With potassium iodide In water for 3h; Inert atmosphere;	24%
Stage #1: 2,6-diamino-9,10-anthraquinone With hydrogenchloride; sodium nitrite In water; acetonitrile Stage #2: With potassium iodide In water; acetonitrile

pyridine (110-86-1) + 11-bromoundecanoyl chloride (15949-84-5) + 2,6-diamino-9,10-anthraquinone (131-14-6) → (9,10-dioxo-2,6-anthracendiyl)bis(imino) bis(11-oxo-11,1-undecandiyl)bis(pyridinium)-diperchlorate

Conditions	Yield
r.t., 3 h; then reflux, 4 h;	63%

Upstream product

• 633-70-5 2,6-dibromoanthraquinone 
• 605-48-1 9,10-dichloroanthracene 
• 7664-93-9 sulfuric acid 
• 605-40-3 2,6-dichloro-9,10-anthraquinone 
• 7664-41-7 ammonia 
• 7758-99-8 copper(II) sulfate 
• 84-50-4 Anthraquinone-2,6-disulfonic acid 
• 110-89-4 piperidine 
• 110-86-1 pyridine 

Downstream Products

• 4478-06-2 2,6-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone 
• 63967-93-1 2,6-Bis(α-piperidinobenzylideneamino)anthraquinone 
• 528609-98-5 2,6-dibromo-9,10-diphenylanthracene 
• 633-70-5 2,6-dibromoanthraquinone 
• 186517-01-1 2,6-dibromoanthracene 
• 46710-42-3 anthracene-2,6-diamine 
• 129-09-9 Algol Yellow-GC 
• 6448-91-5 2,6-diamino-1,5-dichloro-anthraquinone 
• 6470-90-2 2,6-bis-benzoylamino-anthraquinone 
• 1026853-48-4 2,6-bis-benzoylamino-1,5-dichloro-anthraquinone 
• 605-40-3 2,6-dichloro-9,10-anthraquinone 
• 882864-41-7 C₂₈H₁₆Cl₂N₂O₄ 
• 864377-54-8 2,6-bis(3-bromopropionamido)anthracene-9,10-dione 

Related news

Photophysical behaviour of 2,6-Diaminoanthraquinone (cas 131-14-6) in different solvents and at various pH09/30/2019

The absorption and fluorescence spectral properties of 2,6-diaminoanthraquinone (DAAQ) have been investigated in a series of organic solvents of different polarity and in aqueous solutions with H o /pH/H_ in the range −10 to 17. The Stokes shift of DAAQ is correlated with various polarit...detailed

Study of preferential solvation of 2,6-Diaminoanthraquinone (cas 131-14-6) in binary mixtures by absorption and fluorescence studies09/29/2019

The role of solute–solvent and solvent–solvent interaction on the preferential solvation characteristics of 2,6-diaminoanthraquinone (DAAQ) has been analysed by monitoring the optical absorption and fluorescence emission spectra. Binary mixtures consist of dimethylformamide (DMF)–ethanol (EtO...detailed

Relevant articles and documents

Long-wavelength analogue of PRODAN: Synthesis and properties of Anthradan, a fluorophore with a 2,6-donor-acceptor anthracene structure

We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polarity-sensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.