2,6-Diaminoanthraquinone supplier

Name
2,6-Diaminoanthraquinone
EINECS 205-013-7
CAS No. 131-14-6
Article Data11
CAS DataBase
Density 1.456 g/cm³
Solubility
Melting Point >325 °C(lit.)
Formula C₁₄H₁₀N₂O₂
Boiling Point 551.9 °C at 760 mmHg
Molecular Weight 238.246
Flash Point 287.6 °C
Transport Information
Appearance solid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Anthraquinone,2,6-diamino- (7CI,8CI);2,6-Anthraquinonyldiamine;2,6-Diamino-9,10-anthraquinone;NSC 39935;
PSA 86.18000
LogP 2.78880

Synthetic route

: 110-89-4
piperidine

: 110-86-1
pyridine

: 1,1'-(9,10-dioxo-9,10-dihydro-anthracene-2,6-diyl)-bis-pyridinium; dichloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

...Expand

: 605-40-3
2,6-dichloro-9,10-anthraquinone

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

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

: 84-50-4
Anthraquinone-2,6-disulfonic acid

: ammonium hydroxide

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

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

: 605-40-3
2,6-dichloro-9,10-anthraquinone

: 7664-41-7
ammonia

: 7758-99-8
copper(II) sulfate

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

Conditions	Yield
at 200℃;

...Expand

: 605-48-1
9,10-dichloroanthracene

: 7664-93-9
sulfuric acid

A: 605-44-7
2,7-diaminoanthraquinone

B: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

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

...Expand

2.6-dipyridinio-anthraquinone dichloride: 2.6-dipyridinio-anthraquinone dichloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

Conditions	Yield
With piperidine; pyridine

ammonium salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6): ammonium salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6)

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

Conditions	Yield
With sodium chlorate; ammonium hydroxide

sodium-salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6): sodium-salt of 9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6)

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

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: sodium-salt of/the/ 6-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

Conditions	Yield
With ammonia

sodium salt of/the/ anthraquinone-disulfonic acid-(2.6): sodium salt of/the/ anthraquinone-disulfonic acid-(2.6)

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

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;

: 633-70-5
2,6-dibromoanthraquinone

: 131-14-6
2,6-diamino-9,10-anthraquinone

Conditions

Conditions	Yield
With ammonium hydroxide; copper(l) iodide

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 4635-59-0
4-Chlorobutanoyl chloride

: 134916-10-2
2,6-bis(4-chlorobutyramido)anthracene-9,10-dione

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 87120-50-1
2,6-diaminoanthracen-9(10H)-one

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 142-61-0
Hexanoyl chloride

: 1335230-34-6
N,N′-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)dihexanamide

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 633-70-5
2,6-dibromoanthraquinone

Conditions

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%

: 540-80-7
tert.-butylnitrite

Cu(II)Br: Cu(II)Br

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 633-70-5
2,6-dibromoanthraquinone

Conditions

Conditions	Yield
With hydrogenchloride	98.4%

...Expand

: 1734-00-5
3-hydroxy-2-naphthoyl chloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

: C36H22N2O6

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 625-36-5
2-chloropropionyl chloride

: 72966-79-1
2,6-bis(3-chloropropionamido)anthracene-9,10-dione

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 183720-79-8
9H-fluoren-9-ylmethyl N-(3-chloro-3-oxo-propyl)carbamate

: 1007890-01-8
2,6-bis-[N-(3-Fmoc-amino)-propionamide]anthracene-9,10-dione

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 129032-19-5
2,6-diamino-9,10-dihydroanthracene

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 103321-49-9
9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate

: 1060669-72-8
2,6-bis-[N-(2-Fmoc-amino)-acetamide]anthracene-9,10-dione

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 79-04-9
chloroacetyl chloride

: 55077-07-1
N,N’-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-chloroacetamide)

Conditions

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%

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 46710-42-3
anthracene-2,6-diamine

Conditions

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

: 7623-09-8
2-chloropropionyl chloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 62799-41-1
C20H16Cl2N2O4

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 35400-55-6
5-amino-4-hydroxy-2-naphthalenesulphonic acid

: C34H20N6O10S2(2-)*2Na(1+)

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 74-88-4
methyl iodide

: 106580-21-6
2,6-bis(dimethylamino)-9,10-anthraquinone

Conditions

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%

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 541-88-8
Chloroacetic anhydride

: 55077-07-1
N,N’-(9,10-dioxo-9,10-dihydroanthracene-2,6-diyl)bis(2-chloroacetamide)

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 1188-33-6
N,N-dimethylformamide diethyl diacetal

: 2,6-bis-(dimethylamino-methylene-imino)-anthraquinone

Conditions

Conditions	Yield
In pyridine	83%

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 609-65-4
o-chlorobenzoyl chloride

: 882864-41-7
C28H16Cl2N2O4

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 35400-55-6
5-amino-4-hydroxy-2-naphthalenesulphonic acid

: C34H20N6O10S2(2-)*2Na(1+)

Conditions

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;

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 3,7-diamino-9,10-anthraquinone-2,6-disulfonic acid

Conditions

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

: Phosphoroxy chloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 2,6-bis-(dimethylamino-methylene-imino)-anthraquinone

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 2,6-bis-(1-methylpyrrolidone-2-imino)-anthraquinone

Conditions

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

: 1121-60-4
pyridine-2-carbaldehyde

: iron(II) triflate

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 7732-18-5
water

: 75-05-8
acetonitrile

: C156H96Fe4N24O12(8+)*2C2H3N*H2O*8CF3O3S(1-)

Conditions

Conditions	Yield
Reflux;	78%

...Expand

: 74465-80-8
Ni[H2CNCHC2(CH3)(OCH3)C(CH3)NCH2]2(2+)*2PF6(1-)=Ni[H2CNCHC2(CH3)(OCH3)C(CH3)NCH2]2(PF6)2

: 131-14-6
2,6-diamino-9,10-anthraquinone

: Ni[H2CNCHC2(CH3)(NHC14H6O2NH2)C(CH3)NCH2][H2CNCHC2(CH3)(OCH3)C(CH3)NCH2](2+)*2(PF6)(1-)=Ni(C17H25N4O(C14H9N2O2))(PF6)2

Conditions

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%

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 98-88-4
benzoyl chloride

: 6470-90-2
2,6-bis-benzoylamino-anthraquinone

Conditions

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

: dilitium phthalocyanine

: 131-14-6
2,6-diamino-9,10-anthraquinone

: C14H10N2O2*C32H16N8(2-)*2Li(1+)

Conditions

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

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 119-26-6
(2,4-dinitro-phenyl)-hydrazine

: 2,6-diamino-9,10-[di-(2,4-dinitrophenyl)hydrazono]-9H,10H-anthracene

Conditions

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

: 1121-60-4
pyridine-2-carbaldehyde

: nickel(II) tetrafluoroborate hexahydrate

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 75-05-8
acetonitrile

: C156H96N24Ni4O12(8+)*8BF4(1-)*2C2H3N*2H2O

Conditions

Conditions	Yield
Reflux;	67%

...Expand

: 131-14-6
2,6-diamino-9,10-anthraquinone

: 78507-46-7
2,6-diiodoanthracene-9,10-dione

Conditions

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

: 110-86-1
pyridine

: 15949-84-5
11-bromoundecanoyl chloride

: 131-14-6
2,6-diamino-9,10-anthraquinone

: (9,10-dioxo-2,6-anthracendiyl)bis(imino) bis(11-oxo-11,1-undecandiyl)bis(pyridinium)-diperchlorate

Conditions

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

...Expand

2,6-Diaminoanthraquinone Chemical Properties

Chemical Name: 2,6-Diaminoanthraquinone
IUPAC NAME: 2,6-diaminoanthracene-9,10-dione
CAS No.: 131-14-6
EINECS: 205-013-7
RTECS: CB6450000
Molecular Formula: C₁₄H₁₀N₂O₂
Molecular Weight: 238.24 g/mol
Density: 1.456 g/cm³
Melting Point: >325 °C(lit.)
Flash Point: 287.6 °C
Boiling Point: 551.9 °C at 760 mmHg
Following is the structure of 2,6-ANTHRAQUINONYLDIAMINE(131-14-6):

The chemical synonymous of 2,6-ANTHRAQUINONYLDIAMINE(131-14-6) are 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;2,6-DIAMINOANTHRAQUINONE;2,6-ANTHRAQUINONYLDIAMINE.

2,6-Diaminoanthraquinone Uses

2,6-ANTHRAQUINONYLDIAMINE(131-14-6) is used for the manufacture of dyes named GCN,and used as a dye intermediates for the manufature of reductive dye.

2,6-Diaminoanthraquinone Production

Product Categories about 2,6-ANTHRAQUINONYLDIAMINE(131-14-6) are Intermediates of Dyes and Pigments;Aminoanthraquinones;Anthraquinones;C13 to C14;Carbonyl Compounds;Ketones.

2,6-Diaminoanthraquinone Toxicity Data With Reference

1.		eye-rbt 500 mg/24H MLD		28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,122.
2.		mma-sat 100 µg/plate		MUREAV Mutation Research. 40 (1976),203.

2,6-Diaminoanthraquinone Consensus Reports

Reported in EPA TSCA Inventory.

2,6-Diaminoanthraquinone Safety Profile

An eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes:
    Xi: Harmful
Risk Statements about 2,6-ANTHRAQUINONYLDIAMINE(131-14-6):
    R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements about 2,6-ANTHRAQUINONYLDIAMINE(131-14-6):
    S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
    S36 Wear suitable protective clothing.

Product Name

2,6-Diaminoanthraquinone

Synthetic route

2,6-Diaminoanthraquinone Chemical Properties

2,6-Diaminoanthraquinone Uses

2,6-Diaminoanthraquinone Production

2,6-Diaminoanthraquinone Toxicity Data With Reference

2,6-Diaminoanthraquinone Consensus Reports

2,6-Diaminoanthraquinone Safety Profile

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