Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; tin(ll) chloride for 3h; Heating; | 89% |
1-amino-9,10-anthracenedione
N-butylamine
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-butylaminoanthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine at 30℃; for 8h; | A n/a B 79% |
With CoCl2 In butan-1-ol at 80 - 82℃; for 24h; Product distribution; Mechanism; var. metals chlorides; var. cobalt salts; var. time; var. ammount of CoCl2; other 1-alkylaminoantraquinones, antraquinone, 2-aminoantraquinone; | A 4.7 % Chromat. B 58.7 % Chromat. |
With cobalt(II) bromide In butan-1-ol at 30℃; for 8h; | A 2.9 % Chromat. B 63.5 % Chromat. |
Conditions | Yield |
---|---|
anthracene In isopropyl alcohol for 0.166667h; Irradiation; | 75% |
With sodium sulfide | |
With sodium sulfide |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
In nitrobenzene for 19h; Heating; | 68% |
1-amino-9,10-anthracenedione
cyclohexylamine
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-cyclohexylamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine at 40℃; for 20h; | A n/a B 52% |
N-(4-acetylamino-9,10-dioxo-9,10-dihydro-anthracene-1-yl)-acetamide
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide for 3h; Heating; | 43% |
1-amino-9,10-anthracenedione
methylamine
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-(methylamino)anthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine; water at 30℃; for 26h; | A 8.2% B 39% |
SEC-BUTYLAMINE
1-amino-9,10-anthracenedione
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-(s-butylamino)anthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine at 30℃; for 50h; | A n/a B 38% |
n-Octylamine
1-amino-9,10-anthracenedione
A
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine at 30℃; for 30h; | A n/a B 34% C 2.4% |
9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With methylhydrazine for 4h; Heating; | 30% |
1-amino-9,10-anthracenedione
benzylamine
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-(benzylamino)anthraquinone
Conditions | Yield |
---|---|
With CoCl2 In pyridine at 40℃; for 12h; | A 29% B 5.5% |
1-amino-4-nitroanthraquinone
A
1,4-diamino-9,10-anthraquinone
B
4-hydroxy-1-aminoanthraquinone
Conditions | Yield |
---|---|
In water; isopropyl alcohol for 1h; Product distribution; other solvents: methanol, benzene; presence of KOH; other reaction times; reaction with sensitizer.; | A 12% B 20% |
1-methyl-4-nitrosobenzene
1,4-diamino-anthracene-9,10-diol
A
anthracene-1,4,9,10-tetraone
B
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With manganese(IV) oxide; sulfuric acid | |
With sulfuric acid; chlorine | |
With sulfuric acid; bromine |
N-(9,10-dioxo-9,10-dihydro-[1]anthryl)-formamide
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid Erhitzen des Reaktionsprodukts mit wss. Natronlauge und Natriumsulfid; |
2-(2,5-diamino-benzoyl)-benzoic acid
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid at 190℃; |
N-(9,10-dioxo-9,10-dihydro-1-anthryl)oxamic acid
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0℃; Kochen der mit Soda neutralisierten Saeure mit Natriumsulfid; | |
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; HNO3+H2SO4 / 5 °C / man verseift das Reaktionsprodukt mit Soda 2: alkali; sodium sulfide View Scheme |
2-(5-acetylamino-2-amino-benzoyl)-benzoic acid
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid at 190 - 200℃; |
1,4-bis-(toluene-4-sulfonylamino)-anthraquinone
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sulfuric acid |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium sulfide; water |
1,4-diamino-anthracene-9,10-diol
nitrobenzene
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide |
6H-anthra<1,9-cd>isoxazol-6-one
dimethyl amine
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium sulfide; oxygen; potassium nitrate 1.) water, acetonitrile, 15-20 deg C; 2.) aq. ethanol, 3 h, 80 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 90℃; |
solvent blue 35
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-butylaminoanthraquinone
C
1-amino-4-butyrylamidoanthraquinone
Conditions | Yield |
---|---|
With air; tetra(n-butyl)ammonium hydroxide 1.) DMF/propan-2-ol, 30 s, 2.) 2 min; Multistep reaction; | |
With perchloric acid; air; tetra(n-butyl)ammonium hydroxide Mechanism; Product distribution; multistep reaction; variation of the amount of the reagent; | A 85 % Spectr. B 5 % Spectr. C 10 % Spectr. |
1-amino-9,10-anthracenedione
A
1,4-diamino-9,10-anthraquinone
B
1-amino-4-butylaminoanthraquinone
Conditions | Yield |
---|---|
With N-butylamine In butan-1-ol at 80 - 82℃; for 24h; | A 4.7 % Chromat. B 58.7 % Chromat. |
N-(1-Amino-4-anthraquinonyl)-5-amino-2,4-pentadien-1-ol
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran for 1h; Product distribution; |
5-diethylaminoanthra<1,9-c,d>isoxazol-6-one
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium sulfide; oxygen In ethanol at 80℃; for 3h; Yield given; |
5-dibutylaminoanthra<1,9-c,d>isoxazol-6-one
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium sulfide; oxygen In ethanol at 80℃; for 3h; Yield given; |
5-N-amyl-N-benzylaminoanthra<1,9-c,d>isoxazol-6-one
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With sodium sulfide; oxygen In ethanol at 80℃; for 3h; Yield given; |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In 1,2-dichloro-ethane at 30 - 35℃; for 3h; | 96% |
1,4-diamino-9,10-anthraquinone
1,4-dibromoanthracene-9,10-dione
Conditions | Yield |
---|---|
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 5h; Sandmeyer reaction; | 94% |
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; | 94% |
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 5h; | 84% |
9-{2-[(4,7-diisobutoxy-9-phenylcarbamoyl-[1,10]phenanthroline-2-carbonyl)-amino]-phenylcarbamoyl}-4,7-diisobutoxy-[1,10]phenanthroline-2-carboxylic acid
1,4-diamino-9,10-anthraquinone
C126H120N16O18
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Reflux; | 93% |
1,4-diamino-9,10-anthraquinone
acetyl chloride
N-(4-acetylamino-9,10-dioxo-9,10-dihydro-anthracene-1-yl)-acetamide
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 92% |
(1,5-cyclooctadiene)(methoxy)iridium(l) dimer
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
In acetone N2-atmosphere; stirring equimolar amts. for 40 min; evapn., pptn. on hexane addn., filtration, washing (hexane), drying (vac.); elem. anal.; | 92% |
4,7-diisobutoxy-9-phenylcarbamoyl-[1,10]phenanthroline-2-carboxylic acid
1,4-diamino-9,10-anthraquinone
C70H64N8O10
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Reflux; | 91% |
1,4-diamino-9,10-anthraquinone
4-[(4-amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-3-(4-methylbenzoyl)-4-(4-methylphenyl)-2-oxobut-3-enoic acid
Conditions | Yield |
---|---|
In benzene at 20℃; for 48h; | 90% |
C13H10O4
1,4-diamino-9,10-anthraquinone
3-acetyl-4-[(4-amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-4-(4-methylphenyl)-2-oxobut-3-enoic acid
Conditions | Yield |
---|---|
In benzene at 20℃; for 48h; | 90% |
Conditions | Yield |
---|---|
With copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 190℃; for 6h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 88% |
1,4-diamino-9,10-anthraquinone
1,4-diamino-5,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sodium chlorate; sulfuric acid at -5 - 20℃; for 3h; | 88% |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 87% |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 87% |
1,4-diamino-9,10-anthraquinone
4-[(4-amino-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino]-3-(4-methoxybenzoyl)-4-(4-methoxyphenyl)-2-oxobut-3-enoic acid
Conditions | Yield |
---|---|
In benzene at 20℃; for 48h; | 87% |
diethyl sulfate
1,4-diamino-9,10-anthraquinone
1,4-bisethylamino-anthraquinone
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In 1,2-dichloro-ethane at 50 - 55℃; for 3h; | 85% |
1,4-diamino-9,10-anthraquinone
m-Chlorobenzoyl chloride
1,4-bis-(3-chloro-benzoylamino)-anthraquinone
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 85% |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 85% |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With pyridine; sulfuric acid; magnesium sulfate In water | 85% |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
In acetone N2-atmosphere; stirring equimolar amts. for 40 min; evapn., pptn. on hexane addn., filtration, washing (hexane), drying (vac.); elem. anal.; | 85% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0℃; Reflux; | 85% |
With triethylamine In tetrahydrofuran at 0℃; for 1h; Reflux; | 85% |
1,4-diamino-9,10-anthraquinone
4-chloro-benzoyl chloride
1,4-bis-(4-chloro-benzoylamino)-anthraquinone
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 84% |
With pyridine; nitrobenzene | |
With pyridine; nitrobenzene |
1,4-diamino-9,10-anthraquinone
1,4-Dinitroanthracene-9,10-dione
Conditions | Yield |
---|---|
With trifluoroacetyl peroxide In dichloromethane for 2h; Heating; | 84% |
With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane; water at 40℃; for 144h; | 62% |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 84% |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 84% |
1,4-diamino-9,10-anthraquinone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Reflux; | 84% |
1,4-diamino-9,10-anthraquinone
benzoyl chloride
1,4-bisbenzoylaminoanthraquinone
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 83% |
With pyridine; nitrobenzene | |
With chlorobenzene | |
With pyridine; nitrobenzene | |
With nitrobenzene |
Conditions | Yield |
---|---|
With pyridine In various solvent(s) at 20℃; for 24h; | 83% |
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl acetamide at 0 - 20℃; for 24h; | 83% |
1,4-diamino-9,10-anthraquinone
benzoic acid
1,4-bisbenzoylaminoanthraquinone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h; Inert atmosphere; | 83% |
IUPAC Name: 1,4-Diaminoanthracene-9,10-dione
Molecular formula: C14H10N2O2
Formula weight: 238.26 g/mol
EINECS: 204-922-6
Density: 1.456g/cm3
Melting Point: 265-269 °C
Boiling Point: 544.2 °C at 760 mmHg
Refractive Index: 1.757
Molar Volume: 163.6 cm3
Surface Tension: 80.9 dyne/cm
Enthalpy of Vaporization: 82.27 kJ/mol
Flash Point: 282.9 °C
Vapor Pressure: 6.67E-12 mmHg at 25 °C
Molecular Structure of 1,4-Diamino anthraquinone (CAS NO.128-95-0):
XLogP3-AA: 2.6
H-Bond Donor: 2
H-Bond Acceptor: 4
Tautomer Count: 8
Exact Mass: 238.074228
MonoIsotopic Mass: 238.074228
Topological Polar Surface Area: 86.2
Heavy Atom Count: 18
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)N)N
InChI: InChI=1S/C14H10N2O2/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6H,15-16H2
InChIKey: FBMQNRKSAWNXBT-UHFFFAOYSA-N
Product Categories: Intermediates of Dyes and Pigments; Aminoanthraquinones; Anthraquinones; Highly Purified Reagents; Other Categories; Refined Products by Sublimation; Solvent Dyestuff; Amine Monomers; Monomers; Primary Amines
1,4-Diamino anthraquinone (CAS NO.128-95-0) can be used as a synthetic dye intermediate. It is also used for dyeing polyester.
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.: 1972,121. | ||
2. | mmo-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
3. | mma-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
4. | mmo-omi 12,800 µg/L | HEREAY Hereditas. 99 (1983),209. | ||
5. | orl-rat LDLo:5790 mg/kg | 28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,121. | ||
6. | ipr-rat LD50:250 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 21 (12)(1977),27. |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
A poison by intraperitoneal route. Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Mutation data reported. An eye irritant. When heated to decomposition it emits toxic fumes of NOx.
Risk statements: 22
22: Harmful if swallowed.
Safety statements: 22-36/37
36/37: Wear suitable protective clothing and gloves.
22: Do not breathe dust.
1,4-Diamino anthraquinone (CAS NO.128-95-0) is also named as 1,4-Anthraquinonyldiamine ; Acetate Red Violet R ; Acetoquinone Light Heliotrope NL ; Acetylon Fast Red Violet R ; Amacel heliotrope R ; Amaplast Red Violet P 2R ; Artisil Direct Violet 2RP ; Artisil Violet 2RP ; C.I. 61100 ; C.I. Disperse Violet 1 ; C.I. Disperse Violet 9 ; C.I. Solvent Violet 11 ; CCRIS 5603 ; Celanthrene Red Violet R ; Disperse Violet K ; Dispersive Violet K ; Duranol Violet 2R ; Duranol Violet 2R, 1,4-diamino- ; Interchem Disperse Violet 2RH ; Interchem Hisperse Violet 2RH ; Krisolamine ; Resiren Violet TR ; Seacyl Violet R ; Sectacyl Violet Propyl ; Serisol Brilliant Violet 2R ; Setacyl Violet P-R ; Setacyl Violet R ; Transetile Violet P 3R . 1,4-Diamino anthraquinone (CAS NO.128-95-0) is violet powder. It is soluble in benzene, pyridine, nitrobenzene, aniline, slightly soluble in hot acetic acid and ethanol .
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