1,4-DIHYDROXYANTHRAQUINONE supplier

Name
1,4-DIHYDROXYANTHRAQUINONE
EINECS 201-368-7
CAS No. 81-64-1
Article Data141
CAS DataBase
Density 1.54 g/cm³
Solubility <1 g/L (20 °C) in water
Melting Point 198-199 °C(lit.)
Formula C₁₄H₈O₄
Boiling Point 465.3 °C at 760 mmHg
Molecular Weight 240.215
Flash Point 249.3 °C
Transport Information
Appearance orange to red-brown crystalline powder
Safety 22-24/25-36/37-26
Risk Codes 36/37/38-43
Molecular Structure
Hazard Symbols Xi
Synonyms Anthraquinone,1,4-dihydroxy- (8CI);1,4-Dihydroxy-9,10-anthracenedione;1,4-Dihydroxy-9,10-anthraquinone;1,4-Dihydroxyanthraquinone;C.I. 58050;C.I.Solvent Orange 100;C.I. Solvent Orange 86;Chinizarin;Macrolex OrangeGG;NSC 15367;NSC 229036;NSC 40899;NSC 646569;Quinizarin;Quinizarine;Smoke Orange 18;Smoke Orange R;Solvent Orange 100;Solvent Orange 86;
PSA 74.60000
LogP 1.87320

Synthetic route

: 100073-85-6
N-(p-tolyl)-1,4-dihydroxy-9,10-anthraquinone 9-imine

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid at 20℃; for 1h;	100%

: 9a-chloro-5,8-dihydroxy-1-trimethylsilyloxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With pyridine In chloroform for 48h; Ambient temperature;	100%

: 17648-03-2
9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With nitric acid; bentonite for 0.166667h; Product distribution; Further Variations:; Reagents; reaction times; types of irradiation; Oxidation; Irradiation;	100%
With sodium hydroxide; oxygen

: 6119-74-0
1,4-dimethoxyanthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78℃; for 0.166667h;	100%

: 33266-08-9
1,4-dibenzoyloxy-9,10-anthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With water; trifluoroacetic acid at 72℃; for 0.0833333h;	99%

: 2289-36-3
1,4-diacetoxy-9,10-anthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With water; trifluoroacetic acid at 72℃; for 0.0833333h;	96%
Multi-step reaction with 2 steps 1: 4 percent / alkali-metal alcoholate / 70 °C 2: 91 percent / conc. aq. HCl / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: sodium isopropoxide / propan-2-ol / 0.5 h / 70 °C 2: 100 percent / conc. H2SO4 / 1 h / 20 °C View Scheme
With lipase supported in poly(methylmethacrylate) beads; water In cyclohexane at 24.84℃; Enzymatic reaction;

: 85-44-9
phthalic anhydride

: 106-48-9
4-chloro-phenol

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid; boric acid at 190 - 225℃; for 5h;	94%
With fuming sulphuric acid; boric acid at 25℃; for 11h; Temperature; Solvent; Concentration; Reagent/catalyst;	90%
With sulfuric acid; boric acid at 200℃; for 3.5h;	85%

: 98771-41-6
9,10-di(p-tolylamino)-1,4-anthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 1h; Heating;	91%

: 1709-63-3
anthracene-1,4,9,10-tetraone

: 107-15-3
ethylenediamine

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 20269-39-0
6-hydroxy-1,2,3,4-tetrahydronaphtho<2,3-f>quinoxaline-7,12-dione

Conditions

Conditions	Yield
In pyridine Ambient temperature;	A 1.2% B 90.7%
In pyridine at 30℃; for 6h;	A 1.2% B 90.7%

...Expand

: 1709-63-3
anthracene-1,4,9,10-tetraone

: 24454-89-5
2-acetoxy-1,3-butadiene

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 63229-39-0
2-acetoxy-1,4,4a,12a-tetrahydronaphthacene-5,6,11,12-tetrone

C: Acetic acid 9,10,11,14-tetraoxo-1,4,9,10-tetrahydro-4a,9a-[2]buteno-anthracen-2-yl ester

Conditions

Conditions	Yield
In benzene at 55℃; for 96h;	A n/a B 83% C n/a
In benzene at 55℃; for 96h; Title compound not separated from byproducts;

...Expand

: 475-38-7
5,8-Dihydroxy-1,4-naphthoquinone

: 123-73-9
crotonaldehyde

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With benzoic acid; L-proline In toluene at 50℃; for 5h; Inert atmosphere; Enzymatic reaction;	82%

: 129-43-1
1-hydroxyanthraquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid; boric acid for 5h; Irradiation;	81%
With air; sulfuric acid Product distribution; Mechanism; Irradiation; without air (argon);

: 84-65-1
9,10-phenanthrenequinone

A: 605-32-3
2-hydroxy-9,10-anthraquinone

B: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid; boric acid for 5h; Product distribution; Mechanism; Irradiation; other time;	A n/a B 81%

: 85-44-9
phthalic anhydride

: 123-31-9
hydroquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With aluminium trichloride; sodium chloride at 165℃; for 4h; Fridel-Crafts acylation;	80%
With sulfuric acid; boric acid at 200℃; for 3.5h;	55%
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;	44%

: 1-hydroxy-4-fluoro-anthracene-9,10-dione

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sodium trimethylsilanolate In tetrahydrofuran Substitution; stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h;	80%

: 28736-42-7
1,4-difluoroanthracene-9,10-dione

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation;	78%
Multi-step reaction with 2 steps 1: 90 percent / NaOSi(CH3)3 / tetrahydrofuran / stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h 2: 80 percent / NaOSi(CH3)3 / tetrahydrofuran / stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h View Scheme

: 88-95-9
Phthaloyl dichloride

: 150-78-7
1,4-dimethoxybezene

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With aluminium trichloride In nitrobenzene at 80℃; for 0.5h;	72%

: 29525-00-6
2,3-dichloro-1,4-dihydroxyanthracene-9,10-dione

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
Stage #1: 2,3-dichloro-1,4-dihydroxyanthracene-9,10-dione With iron In acetic acid for 0.75h; Dehalogenation; reduction; Heating; Stage #2: With oxygen In sodium hydroxide pH=8 - 9; Oxidation;	72%

: 84-65-1
9,10-phenanthrenequinone

A: 605-32-3
2-hydroxy-9,10-anthraquinone

B: 129-43-1
1-hydroxyanthraquinone

C: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid at 25℃; Irradiation;	A 70% B n/a C n/a
With sulfuric acid at 25℃; Irradiation; prolonged irradiation;	A n/a B 55% C 6%

...Expand

: 106-48-9
4-chloro-phenol

: 88-99-3
benzene-1,2-dicarboxylic acid

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With sulfuric acid; boric acid at 230℃; for 0.166667h; Product distribution; Further Variations:; Temperatures; Reagents; reaction times; microwave powers; microwave irradiation;	68.3%

: 123-31-9
hydroquinone

: 88-95-9
Phthaloyl dichloride

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With aluminium trichloride In nitrobenzene at 100℃; for 0.5h;	65%
With aluminium trichloride; C6H4NO2 at 165℃; for 4h; Fridel-Crafts acylation;

: 51287-54-8
3-(phenylsulfanyl)isobenzofuran-1(3H)-one

: 106-51-4
p-benzoquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
Stage #1: 3-(phenylsulfanyl)isobenzofuran-1(3H)-one With lithium tert-butoxide In tetrahydrofuran at -60℃; for 0.416667h; Stage #2: p-benzoquinone In tetrahydrofuran at -60 - 20℃; Hauser annulation; Further stages.;	56%

: 82-34-8
1-nitroanthraquinone

A: 129-43-1
1-hydroxyanthraquinone

B: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

C: 72-48-0
1,2-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
With potassium hydroxide; Cumene hydroperoxide In dimethyl sulfoxide at 15 - 25℃; for 10h;	A 55% B 13% C 32%
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 3h;	A 45% B 8% C 35%

...Expand

: 27613-27-0
3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile

: 106-51-4
p-benzoquinone

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

Conditions

Conditions	Yield
Stage #1: 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile With lithium tert-butoxide In tetrahydrofuran at -60℃; for 0.416667h; Stage #2: p-benzoquinone In tetrahydrofuran at -60 - 20℃; Hauser annulation; Further stages.;	52%

: 67-56-1
methanol

: 41099-45-0
2,10-hydroxy-9-chloro-1,4-anthraquinone

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 7336-64-3
1-hydroxy-4-methoxyanthracene-9,10-dione

Conditions

Conditions	Yield
With perchloric acid for 12h; Heating;	A 36% B 49%

...Expand

: 38399-72-3
leuco-1,4-dihydroxyanthraquinone

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 128885-71-2
dihydroxy-1,4 (hydroxy-3 propyl)-2 anthraquinone-9,10

C: 111301-39-4
(-)-(S)<(dimethyl-2,2 dioxolanne-1,3 yl-4) methyl>-2 dihydroxy-1,4 anthraquinone-9,10

D: 111301-40-7, 111331-26-1
<(dimethyl-2,2 dioxolanne-1,3 yl-4) hydroxymethyl>-2 dihydroxy-1,4 anthraquinone-9,10

Conditions

Conditions	Yield
With potassium hydroxide; sodium hydrogensulfite Product distribution; 1.) MeOH, 15 min, 20 deg C, 2.) MeOH, 12 h, 20 deg C, further temperatures;	A 33% B 4% C 22% D 37%

...Expand

: 79207-97-9
1,4-bis(prop-2'-enyloxy)-9,10-anthraquinone

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 79208-09-6
1,4-dihydroxy-2-(prop-2'-enyl)-9,10-anthraquinone

C: 79208-01-8
2,3-diallyl-1,4-dihydroxyanthraquinone

D: 79208-08-5
1-hydroxy-4-propanoyl-2-(prop-2'-enyl)anthraquinone

Conditions

Conditions	Yield
In 1,2-dichloro-benzene for 25h; Heating;	A 5% B 32% C 14% D 18%

...Expand

: 14569-45-0
5,8-diacetoxy-1,4-naphthoquinone

: 108030-46-2
(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 27573-16-6
5-nitro-1,4-dihydroxy-9,10-anthracenedione

C: 117554-15-1
Acetic acid 4-hydroxy-5-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

D: 117554-14-0
Acetic acid 4-hydroxy-8-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Conditions

Conditions	Yield
In xylene for 24h; Ambient temperature;	A 4.2% B 30.2% C n/a D n/a
In xylene for 24h; Ambient temperature; Title compound not separated from byproducts;	A 4.2% B 30.2% C n/a D n/a

...Expand

: 108030-46-2
(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene

: 475-38-7
5,8-Dihydroxy-1,4-naphthoquinone

A: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

B: 27573-16-6
5-nitro-1,4-dihydroxy-9,10-anthracenedione

C: 117554-13-9
2-(dimethylamino)-5,8-dihydroxynaphthalene-1,4-dione

Conditions

Conditions	Yield
In xylene for 12h; Ambient temperature;	A 9.2% B 14.1% C 24.9%

...Expand

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 106-95-6
allyl bromide

: 79207-97-9
1,4-bis(prop-2'-enyloxy)-9,10-anthraquinone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 16h;	100%
With potassium carbonate In acetone for 48h; Reflux;	89%
With tetraethylammonium bromide; potassium carbonate; sodium hydroxide at 85℃; for 0.5h; Microwave irradiation; Sealed tube;	85%
With potassium carbonate In acetone Heating;	81%
With potassium carbonate In acetone Reflux;

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 77-78-1
dimethyl sulfate

: 6119-74-0
1,4-dimethoxyanthraquinone

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 480h; Ambient temperature;	99%
With potassium carbonate In acetone for 4h; Reflux;	96%
With potassium carbonate In acetone for 72h; Heating;	95%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 107-15-3
ethylenediamine

: 15077-66-4
6-hydroxy-1,2,3,4-tetrahydronaphtho[2,3-f]-quinoxaline-7,12-dione

Conditions

Conditions	Yield
With [bmim]PF6; copper dichloride at 20℃; for 2h; Product distribution; Further Variations:; Reagents;	99%

: 14285-68-8
decacarbonyldirhenium(0)

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 7128-64-5
Uvitex OB

: 918153-35-2
[(Re(CO)3)4(2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene)2(1,4-dihydroxy-9,10-anthraquinone(-2H))2]

Conditions

Conditions	Yield
In 1,2,5-trimethyl-benzene under reflux;	99%

...Expand

: 34841-06-0
3-bromo-4-methoxybenzylaldehyde

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 2-((3-bromo-4-methoxyphenyl)(hydroxy)methyl)-1,4-dihydroxyanthracene-9,10-dione

Conditions

Conditions	Yield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With potassium hydroxide In methanol; water for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 3-bromo-4-methoxybenzylaldehyde With sodium dithionite In methanol; water Time;	99%
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium dithionite; potassium hydroxide In methanol; water for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: 3-bromo-4-methoxybenzylaldehyde In methanol; water at 0℃; for 4h; Inert atmosphere; Stage #3: With dihydrogen peroxide In water for 0.333333h;	76%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 635-12-1
1,4-anthraquinone

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol for 24h; Heating;	98%
With methanol; sodium tetrahydroborate at 0℃;	98%
With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;	97%

: 78-88-6
2,3-Dichloroprop-1-ene

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 72183-81-4
1,4-Bis-(2-chloro-allyloxy)-anthraquinone

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 344h; Heating;	98%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 107-15-3
ethylenediamine

: 20269-39-0
6-hydroxy-1,2,3,4-tetrahydronaphtho<2,3-f>quinoxaline-7,12-dione

Conditions

Conditions	Yield
copper dichloride In pyridine at 30℃; for 24h; Product distribution; Mechanism; further copper chloride catalyst, effect of oxygen without catalyst, further amine;	98%
With copper dichloride In pyridine at 30℃; for 6h; Product distribution; other diamines, also in the absence of a copper salts;	98%
copper dichloride In pyridine at 30℃; for 24h;	98%
With oxygen; copper dichloride In pyridine at 30℃; for 6h;	98%
With copper dichloride Ambient temperature;	33%

: 476-60-8
leucoquinizarin

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 122-80-5
N-acetyl-p-phenylenediamine

: C22H16N2O4

Conditions

Conditions	Yield
Stage #1: N-acetyl-p-phenylenediamine With hydrogenchloride In water at 40 - 50℃; for 0.5h; Stage #2: leucoquinizarin; 1,4-dihydroxy-9,10-anthracenedione In water at 85 - 90℃; Solvent; Temperature;	97.13%

...Expand

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 106-49-0
p-toluidine

: 128-80-3
D and C green 6

Conditions

Conditions	Yield
With leucoquinizarin; boric acid; sodium hydrogensulfite In ethanol; benzene at 62 - 66℃; for 12h; Temperature; Solvent;	97%
With 1-butyl-3-ethyl-1H-imidazolium tetrafluoroborate at 85 - 125℃; Reagent/catalyst; Temperature; Green chemistry; Large scale;	95.9%
With boric acid; calcium carbonate; tin(ll) chloride at 110 - 130℃;

: 421-83-0
trifluoromethane sulfonyl chloride

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 96701-08-5
1,4-Bis-(trifluoromethanesulfonyloxy)-9,10-anthracenedione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate In dichloromethane at 5 - 10℃; for 0.5h;	97%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 106-95-6
allyl bromide

: 10-[1-(prop-2-enyl)]-1,4,10-trihydroxy-9(10H)-anthracenone

Conditions

Conditions	Yield
With indium; water In tetrahydrofuran; methanol at 30℃; Barbier allylation;	97%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 106-94-5
propyl bromide

: 847901-15-9
1,4-dipropoxy-9,10-anthraquinone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Heating;	97%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Williamson Ether Synthesis; Inert atmosphere;	89%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 38399-72-3
leuco-1,4-dihydroxyanthraquinone

: 106-50-3
1,4-phenylenediamine

: C20H14N2O3

Conditions

Conditions	Yield
With boric acid In butan-1-ol for 16h; Reagent/catalyst; Reflux;	97%

...Expand

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 17648-03-2
9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

Conditions

Conditions	Yield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium carbonate In water at 85℃; Inert atmosphere; Stage #2: With sodium dithionite In water Inert atmosphere;	96.1%
With sodium disulfite; potassium carbonate Hydrogenation;	93%
With acetic acid; aluminium; indium(III) chloride In ethanol; water at 90℃; for 11h;	78%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: silver nitrate

: 620591-70-0
C14H6(O)2(OAg)2

Conditions

Conditions	Yield
With triethylamine In ethanol; triethylamine; acetonitrile byproducts: NEt3*HNO3; a soln. of quinone in Et3N and EtOH were added dropwise under N2 to a soln. of AgNO3 in MeCN-EtOH in the dark at 25°C, the mixt. was stirred for 2 h; filtd., ppt. was washed with cold EtOH, filtrate evapd. under vac.; elem. anal.;	96%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 106-96-7
propargyl bromide

: 1045-75-6
1,4-bis(prop-2-ynyloxy)anthracene-9,10-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	96%
With potassium carbonate In acetone for 120h; Schlenk technique; Reflux;	23%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: leuco-1,4-dihydroxyanthraquinone

Conditions

Conditions	Yield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium hydroxide In water at 70 - 75℃; for 0.5h; Stage #2: With thiourea In water at 88℃; for 2h; Reagent/catalyst;	96%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 109-73-9
N-butylamine

: 17354-14-2
solvent blue 35

Conditions

Conditions	Yield
With acetic acid; sodium sulfate In ethanol for 4h; Reflux;	95.3%
With sodium dithionite; ethanol

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 74-89-5
methylamine

: 2475-44-7
disperse blue 14

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; tetrafluoroboric acid; bromobutyric acid In methanol at 50 - 55℃; Temperature; Large scale;	95.1%
With ethanol; sodium carbonate; copper(II) sulfate at 140℃;
With sodium hydroxide; copper(II) sulfate at 140℃;

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 109-76-2
Trimethylenediamine

: 2-(3'-aminopropylamino)-1,4-dihydroxyanthraquinone

Conditions

Conditions	Yield
copper dichloride In pyridine at 30℃; for 24h;	95%
With oxygen; copper dichloride In pyridine at 30℃; for 6h;	95%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 109-77-3
malononitrile

: 86092-18-4
2-amino-3-cyano-5-hydroxyanthra<1,2-b>furan-6,11-dione

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide Ambient temperature;	95%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 74-88-4
methyl iodide

: 6119-74-0
1,4-dimethoxyanthraquinone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃;	95%
With aluminum oxide; potassium fluoride In dimethyl sulfoxide at 35℃; for 10h;	58.5%
With potassium carbonate In acetone Reflux;	31.5%

: 81-64-1
1,4-dihydroxy-9,10-anthracenedione

: 13076-29-4
1,4-dimethoxyanthracene

Conditions

Conditions	Yield
With hydrogenchloride; sodium borohydrid In methanol	95%
Multi-step reaction with 3 steps 1: 83 percent / K2CO3 / 1,2-dichloro-benzene / 1 h / Heating 2: 100 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 3: 40 percent / HCl / tetrahydrofuran / 2 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: 62 percent / Zn; glacial acetic acid / 15 h / Heating View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran / 24 h / Reflux 2: zinc; acetic acid / 96 h / Reflux View Scheme

1,4-DIHYDROXYANTHRAQUINONE Chemical Properties

IUPAC Name:1,4-dihydroxyanthracene-9,10-dione
Molecular Formula:C₁₄H₈O₄
Molecular Weight:240.210920 g/mol
Appearance:red-brown powder
Melting Point:198-199 °C(lit.)
Boiling Point:450 °C
Flash Point:222 °C
vapor density:8.3 (vs air)
vapor pressure:1 mm Hg ( 196.7 °C)
Colour Index:58050
Water Solubility:<1 g/L (20 oC)
Merck:14,8064
BRN:1914036
Synonyms of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
1,4-dihydroxy-9,10-anthracenedione;1,4-DIHYDROXYANTHRAQUINONE;1,4 DIHYROXY AQ;DSD ACID;CI NO 58050;CI 58050;LABOTEST-BB LT00052844;PIGMENT VIOLET 12
Categories of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Hydroxyanthraquinones;Solvent Dyestuff

1,4-DIHYDROXYANTHRAQUINONE Uses

1,4-DIHYDROXYANTHRAQUINONE(81-64-1) is an important dye intermediate used to make Disperse Blue HSR, Disperse Blue 5R, Disperse Blue B, scattered dark blue RB, anthraquinone acid blue R, brilliant blue RAW Weak Acid Green GS, to restore the gray BG, Vat Brown BR, etc.

1,4-DIHYDROXYANTHRAQUINONE 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.: 1972,102.
2.	mmo-sat 100 µg/plate	MUREAV Mutation Research. 40 (1976),203.
3.	ipr-rat LD50:2100 mg/kg	GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 21 (12)(1977),27.
4.	ivn-mus LD50:320 mg/kg	CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#03274 .

1,4-DIHYDROXYANTHRAQUINONE Consensus Reports

Reported in EPA TSCA Inventory.

1,4-DIHYDROXYANTHRAQUINONE Safety Profile

Safety Information of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Hazard Codes:Xi

Risk Statements:36/37/38-43
36/37/38:Irritating to eyes, respiratory system and skin
43:May cause sensitization by skin contact
Safety Statements:22-24/25-36/37-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:2
RTECS:CB6600000
Poison by intravenous route. Moderately toxic by intraperitoneal route. Mutation data reported. An eye irritant. A weak allergen. When heated to decomposition it emits acrid smoke and irritating fumes.

1,4-DIHYDROXYANTHRAQUINONE Specification

First Aid Measures of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.

Storage of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

Product Name

1,4-DIHYDROXYANTHRAQUINONE

Synthetic route

1,4-DIHYDROXYANTHRAQUINONE Chemical Properties

1,4-DIHYDROXYANTHRAQUINONE Uses

1,4-DIHYDROXYANTHRAQUINONE Toxicity Data With Reference

1,4-DIHYDROXYANTHRAQUINONE Consensus Reports

1,4-DIHYDROXYANTHRAQUINONE Safety Profile

1,4-DIHYDROXYANTHRAQUINONE Specification

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