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145-49-3

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145-49-3 Usage

Uses

1,5-Diamino-4,8-dihydroxy-9,10-anthracenedione is a useful building block for organic synthesis.

Safety Profile

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

Check Digit Verification of cas no

The CAS Registry Mumber 145-49-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 145-49:
(5*1)+(4*4)+(3*5)+(2*4)+(1*9)=53
53 % 10 = 3
So 145-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H10N2O4/c15-5-1-3-7(17)11-9(5)13(19)12-8(18)4-2-6(16)10(12)14(11)20/h1-4,17-18H,15-16H2

145-49-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,5-Diamino-4,8-dihydroxyanthraquinone

1.2 Other means of identification

Product number -
Other names 1,5-DIAMINO-4,8-DIHYDROXYANTHRAQUINONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:145-49-3 SDS

145-49-3Synthetic route

1,5-dihydroxy-4,8-dinitro-anthraquinone
128-91-6

1,5-dihydroxy-4,8-dinitro-anthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sodium hydroxide; palladium-carbon In hydrogen97.8%
1,5-diaminoanthraquinone
129-44-2

1,5-diaminoanthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
Stage #1: 1,5-diaminoanthraquinone With sulfuric acid at 0℃; for 0.25h;
Stage #2: With sodium chlorate at 0 - 20℃; for 3.75h;
83%
Alizarin Saphirol B
128-86-9

Alizarin Saphirol B

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sodium dithionite; water; boric acid
durch Abspaltung beider Sulfogruppen;
With pyridine; sodium dithionite; water
1,5-diaminoanthraquinone
129-44-2

1,5-diaminoanthraquinone

A

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

B

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid
With manganese(IV) oxide; sulfuric acid
1,5-diazido-anthraquinone
85192-94-5

1,5-diazido-anthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sulfuric acid
Alizarin Saphirol B
128-86-9

Alizarin Saphirol B

water
7732-18-5

water

Na2S2O4

Na2S2O4

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

4.8-dinitro-anthrarufin

4.8-dinitro-anthrarufin

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride weiteres Reagens: Wasser;
sodium-salt of/the/ 4.8-diamino-1.5-dihydroxy-9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6)

sodium-salt of/the/ 4.8-diamino-1.5-dihydroxy-9.10-dioxo-9.10-dihydro-anthracene-disulfonic acid-(2.6)

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sodium hydroxide; zinc anschliessendes Erwaermen;
sodium salt of/the/ 4.8-diamino-anthrarufin-disulfonic acid-(2.6)

sodium salt of/the/ 4.8-diamino-anthrarufin-disulfonic acid-(2.6)

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sodium dithionite at 85 - 90℃;
sodium salt of/the/ 4.8-diamino-anthrarufin-sulfonic acid-(2)

sodium salt of/the/ 4.8-diamino-anthrarufin-sulfonic acid-(2)

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sodium dithionite; water Kochen des Reaktionsprodukts mit Sodaloesung;
sulfuric acid
7664-93-9

sulfuric acid

1,5-diaminoanthraquinone
129-44-2

1,5-diaminoanthraquinone

manganese dioxide

manganese dioxide

A

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

B

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

Conditions
ConditionsYield
at 30 - 40℃;
1.5-dinitroanthraquinone
82-35-9

1.5-dinitroanthraquinone

A

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

B

x.x-diamino-x.x-dioxy-anthraquinone

x.x-diamino-x.x-dioxy-anthraquinone

Conditions
ConditionsYield
With sulfuric acid; sulfur das Produkt bei 40-45grad halten, in Schwefelsaeure giessen und mit Wasser versetzen, bis die Temperatur auf 100-110grad gestiegen ist;
1,5-bis-hydroxyamino-anthraquinone
60080-32-2

1,5-bis-hydroxyamino-anthraquinone

A

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

B

x.x-diamino-x.x-dioxy-anthraquinone

x.x-diamino-x.x-dioxy-anthraquinone

Conditions
ConditionsYield
With sulfuric acid; water
hydrogenchloride
7647-01-0

hydrogenchloride

1,5-dihydroxy-4,8-dinitro-anthraquinone
128-91-6

1,5-dihydroxy-4,8-dinitro-anthraquinone

SnCl2

SnCl2

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

sulfuric acid
7664-93-9

sulfuric acid

1,5-diazido-anthraquinone
85192-94-5

1,5-diazido-anthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

sulfuric acid
7664-93-9

sulfuric acid

1,5-bis-hydroxyamino-anthraquinone
60080-32-2

1,5-bis-hydroxyamino-anthraquinone

water
7732-18-5

water

A

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

B

x.x-diamino-x.x-dioxy-anthraquinone

x.x-diamino-x.x-dioxy-anthraquinone

Conditions
ConditionsYield
at 100 - 110℃;
1.5-dinitroanthraquinone
82-35-9

1.5-dinitroanthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tin dichloride; water; NaOH-solution / Verduennen und Filtrieren in ein Gemisch aus konz. Salzsaeure und Wasser
2: concentrated sulfuric acid; water
View Scheme
In ice-water; sulfuric acid; N,N-dimethyl-formamide
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

A

1,4,5,8-tetrahydroxy-anthraquinone
81-60-7

1,4,5,8-tetrahydroxy-anthraquinone

B

1-amino-4,5,8-trihydroxyanthraquinone
6374-78-3

1-amino-4,5,8-trihydroxyanthraquinone

C

leuco-1,4,5,8-tetrahydroxyanthraquinone
69837-14-5

leuco-1,4,5,8-tetrahydroxyanthraquinone

D

5-Amino-8,9,10-trihydroxy-2,3-dihydro-anthracene-1,4-dione

5-Amino-8,9,10-trihydroxy-2,3-dihydro-anthracene-1,4-dione

Conditions
ConditionsYield
With sodium dithionite In water at 100℃; for 0.666667h;A 2.5%
B 1.3%
C 92%
D 6.4%
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,4,5,8-tetrahydroxy-anthraquinone
81-60-7

1,4,5,8-tetrahydroxy-anthraquinone

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite at 100℃; for 1h;80%
With hydrogenchloride at 180℃;
With sodium dithionite; nitrobenzene 1.) 100 deg C; Multistep reaction;
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

1,5-diamino-2,6-di(p-dimethylanilino)-4,8-dihydroxyanthraquinone

1,5-diamino-2,6-di(p-dimethylanilino)-4,8-dihydroxyanthraquinone

Conditions
ConditionsYield
With hydrogenchloride; aluminium trichloride at 20℃; for 2h;75%
Na2S4

Na2S4

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

leuco-1,4,5,8-tetrahydroxyanthraquinone
23478-60-6

leuco-1,4,5,8-tetrahydroxyanthraquinone

Conditions
ConditionsYield
With sodium hydroxide In water74%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

2-(2-((5-amino-4,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-1-yl)amino)ethyl)isoindoline-1,3-dione

2-(2-((5-amino-4,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-1-yl)amino)ethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 24h;61%
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

epichlorohydrin
106-89-8

epichlorohydrin

[1,5-(chloro-2-hydroxypropylamino)-4,8-dihydroxy]-9,10-anthracenedione

[1,5-(chloro-2-hydroxypropylamino)-4,8-dihydroxy]-9,10-anthracenedione

Conditions
ConditionsYield
With acetic acid at 90℃; for 0.5h;56%
methanol
67-56-1

methanol

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

Disperse blue 26
3860-63-7

Disperse blue 26

Conditions
ConditionsYield
With sulfuric acid at 170℃;
tetraacetyl diborate
5187-37-1

tetraacetyl diborate

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-bis-acetylamino-4,8-bis-diacetoxyboranyloxy-anthraquinone

1,5-bis-acetylamino-4,8-bis-diacetoxyboranyloxy-anthraquinone

Conditions
ConditionsYield
With acetic anhydride
m-(trifluoromethyl)benzoyl fluoride
328-99-4

m-(trifluoromethyl)benzoyl fluoride

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-dihydroxy-4,8-bis-(3-trifluoromethyl-benzoylamino)-anthraquinone
6417-47-6

1,5-dihydroxy-4,8-bis-(3-trifluoromethyl-benzoylamino)-anthraquinone

Conditions
ConditionsYield
With pyridine; nitrobenzene
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

4-trifluoromethyl-benzoyl fluoride
368-94-5

4-trifluoromethyl-benzoyl fluoride

1,5-dihydroxy-4,8-bis-(4-trifluoromethyl-benzoylamino)-anthraquinone

1,5-dihydroxy-4,8-bis-(4-trifluoromethyl-benzoylamino)-anthraquinone

Conditions
ConditionsYield
With pyridine; nitrobenzene
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

3-Bromoalizarin
18084-26-9

3-Bromoalizarin

1,5-bis-(3,4-dihydroxy-9,10-dioxo-9,10-dihydro-[2]anthrylamino)-4,8-dihydroxy-anthraquinone

1,5-bis-(3,4-dihydroxy-9,10-dioxo-9,10-dihydro-[2]anthrylamino)-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
With sodium acetate; nitrobenzene; copper dichloride
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

4,8-diamino-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid
5138-23-8

4,8-diamino-1,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid

Conditions
ConditionsYield
With sulfuric acid; boric acid
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,4,5,8,10-pentahydroxy-anthrone

1,4,5,8,10-pentahydroxy-anthrone

Conditions
ConditionsYield
With alkaline aqueous Na2S2O4
With sodium dithionite
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1-amino-4,5,8-trihydroxyanthraquinone
6374-78-3

1-amino-4,5,8-trihydroxyanthraquinone

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid Versetzen mit Wasser und anschliessendes Erwaermen;
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

1,5-diamino-2,4,6,8-tetrahydroxy-anthraquinone

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid man behandelt die erhaltene Verbindung in konz. Schwefelsaeure mit krystallinischer Borsaeure;
tetraacetyl diborate
5187-37-1

tetraacetyl diborate

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

acetic anhydride
108-24-7

acetic anhydride

1,5-bis-acetylamino-4,8-bis-diacetoxyboranyloxy-anthraquinone

1,5-bis-acetylamino-4,8-bis-diacetoxyboranyloxy-anthraquinone

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

acetic anhydride
108-24-7

acetic anhydride

1,5-bis-acetylamino-4,8-dihydroxy-anthraquinone
121614-37-7

1,5-bis-acetylamino-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
With acetic acid
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

5-chlorosulfonyl-2-hydroxybenzoic acid
17243-13-9

5-chlorosulfonyl-2-hydroxybenzoic acid

1,5-bis-(3-carboxy-4-hydroxy-benzenesulfonylamino)-4,8-dihydroxy-anthraquinone

1,5-bis-(3-carboxy-4-hydroxy-benzenesulfonylamino)-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
With sodium acetate; nitrobenzene at 120℃;
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

benzoyl chloride
98-88-4

benzoyl chloride

1,5-bis-benzoylamino-4,8-dihydroxy-anthraquinone
6370-58-7

1,5-bis-benzoylamino-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
With nitrobenzene
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,5-bis-(2-chloro-acetylamino)-4,8-dihydroxy-anthraquinone
121614-42-4

1,5-bis-(2-chloro-acetylamino)-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
With nitrobenzene
4-heptylbenzoyl chloride
50606-96-7

4-heptylbenzoyl chloride

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-bis-(4-n-heptylbenzoylamino)-4,8-dihydroxy-anthraquinone

1,5-bis-(4-n-heptylbenzoylamino)-4,8-dihydroxy-anthraquinone

Conditions
ConditionsYield
In chlorobenzene for 1h; Heating;
4-heptylbenzoyl chloride
50606-96-7

4-heptylbenzoyl chloride

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-bis-(4-n-heptylbenzoylamino)-4,8-bis-(4-n-heptylbenzoyloxy)-anthraquinone

1,5-bis-(4-n-heptylbenzoylamino)-4,8-bis-(4-n-heptylbenzoyloxy)-anthraquinone

Conditions
ConditionsYield
In pyridine for 0.5h; Heating;
4-pentylbenzoyl chloride
49763-65-7

4-pentylbenzoyl chloride

4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

C38H38N2O6

C38H38N2O6

Conditions
ConditionsYield
With pyridine
4,8-diamino-1,5-dihydroxyanthraquinone
145-49-3

4,8-diamino-1,5-dihydroxyanthraquinone

1,5-dihydroxyanthraquinone
117-12-4

1,5-dihydroxyanthraquinone

Conditions
ConditionsYield
With sulfuric acid; N,N-dimethyl-formamide; sodium nitrite 1) water, 0 deg C, 2 h, 2) 65 deg C, 180 min; Yield given. Multistep reaction;

145-49-3Relevant articles and documents

ANTHARQUINONE COMPOUNDS AS ANTI CANCER COMPOUNDS

-

Page/Page column 18-19, (2008/06/13)

Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R1 to R4 are each selected from the group consisting of H, C1-4 alkyl, X1, -NHR0N (R5)2 in which R0 is a C1-12 alkanediyl and each R5 is H or optionally substituted C1-4 alkyl, and a group of formula (II) in which at least one of R6,R7 and R8 is selected from X2 , and X2 substituted C1-4 alkyl and any others are H or C1-4 alkyl; R9 is selected from H, C1-4 alkyl, X2 and X2 substituted C1-4 alkyl; m is 0 or 1; n is 1 or 2; X1 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; and X2 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R1 to R4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.

Process for the manufacture of aminohydroxyanthraquinones

-

, (2008/06/13)

The invention relates to a process for the manufacture of an aminohydroxyanthraquinone of the formula STR1 wherein both of X are hydrogen or one X is --NH2 and the other is --OH and Z is hydrogen, C1 -C4 alkyl or carboxyl, with the proviso that, if Z is C1 -C4 alkyl or carboxyl, both of X must be hydrogen, which process comprises reacting a nitroanthraquinone of the formula STR2 wherein both of Y are hydrogen or one Y is --NO2 and the other is hydrogen and Z is as defined for formula (1), with the proviso that, if Z is C1 -C4 alkyl or carboxyl, both of Y must be hydrogen, in an aprotic dipolar solvent, with an alkali metal azide or alkaline earth metal azide, in the temperature range between 0° and 30° C. The reaction products are disperse dyes or intermediates for obtaining vat dyes and disperse dyes.

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