Product Name

  • Name

    Diacerein

  • EINECS 237-310-2
  • CAS No. 13739-02-1
  • Article Data35
  • CAS DataBase
  • Density 1.491 g/cm3
  • Solubility 240μg/L at 25℃
  • Melting Point 217-218 °C
  • Formula C19H12O8
  • Boiling Point 631.5 °C at 760 mmHg
  • Molecular Weight 368.299
  • Flash Point 231.8 °C
  • Transport Information
  • Appearance yellow crystalline solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 13739-02-1 (Diacerein)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo- (9CI);4,5-diacetyloxy-9,10-dioxo-anthracene-2-carboxylic acid;4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;Fisiodar;9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate;Diacereine [French];Artrodar;9,10-Dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylic acid;
  • PSA 124.04000
  • LogP 2.01080

Synthetic route

1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

acetic anhydride
108-24-7

acetic anhydride

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With pyridine; dmap100%
With dmap; triethylamine In acetic anhydride at 20℃; for 1h;95%
With pyridine at 120℃; for 6h;93%
1,8-diacetoxy-3-carboxaldehyde-9,10-anthraquinone

1,8-diacetoxy-3-carboxaldehyde-9,10-anthraquinone

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate dihydrate; water In dimethyl sulfoxide; acetone for 9h;54.6%
With chromium trioxide-pyridine complex In pyridine at 0 - 5℃; for 6h; Oxidation;5 mg
1,8-diacetoxy-3-methyl-anthraquinone
18713-45-6

1,8-diacetoxy-3-methyl-anthraquinone

acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

chromic acid

chromic acid

diacetylrhein
13739-02-1

diacetylrhein

...Expand
acetylated barbaloin

acetylated barbaloin

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With chromium(VI) oxide; acetic anhydride; acetic acid
1,8,9-triacetoxy-3-methyl-anthracene
61446-06-8

1,8,9-triacetoxy-3-methyl-anthracene

acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

chromic acid

chromic acid

diacetylrhein
13739-02-1

diacetylrhein

...Expand
chrysophanic acid diacetate

chrysophanic acid diacetate

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With acetic anhydride; chromic acid; acetic acid
(2,4-dibromo-6-hydroxyphenyl)-(2-hydroxyphenyl)methanone
820243-52-5

(2,4-dibromo-6-hydroxyphenyl)-(2-hydroxyphenyl)methanone

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 87 percent / K2CO3 / dimethylformamide / 12 h / 80 °C
2: 92 percent / Et3N; (dppf)PdCl2; dppf / dimethylformamide / 18 h / 80 °C / 750.06 Torr
3: KOH / methanol / 48 h / 60 °C
4: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
5: 50 percent / AlCl3; NaCl / 2 h / 150 °C
6: 75 percent / Et3N / 1 h / 20 °C
View Scheme
5-hydroxy-4-(2-hydroxybenzoyl)isophthalic acid
820243-51-4

5-hydroxy-4-(2-hydroxybenzoyl)isophthalic acid

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / AlCl3; NaCl / 2 h / 150 °C
2: 75 percent / Et3N / 1 h / 20 °C
View Scheme
(2-benzyloxy-4,6-dibromophenyl)-(2-benzyloxyphenyl)methanone
820243-54-7

(2-benzyloxy-4,6-dibromophenyl)-(2-benzyloxyphenyl)methanone

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / Et3N; (dppf)PdCl2; dppf / dimethylformamide / 18 h / 80 °C / 750.06 Torr
2: KOH / methanol / 48 h / 60 °C
3: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
4: 50 percent / AlCl3; NaCl / 2 h / 150 °C
5: 75 percent / Et3N / 1 h / 20 °C
View Scheme
5-benzyloxy-4-(2-benzyloxybenzoyl)isophthalic acid dimethyl ester
820243-55-8

5-benzyloxy-4-(2-benzyloxybenzoyl)isophthalic acid dimethyl ester

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: KOH / methanol / 48 h / 60 °C
2: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
3: 50 percent / AlCl3; NaCl / 2 h / 150 °C
4: 75 percent / Et3N / 1 h / 20 °C
View Scheme
5-benzyloxy-4-(2-benzyloxy-benzoyl)-isophthalic acid
1026688-54-9

5-benzyloxy-4-(2-benzyloxy-benzoyl)-isophthalic acid

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 414 mg / H2 / Pd/C / ethanol / 12 h / 20 °C / 750.06 Torr
2: 50 percent / AlCl3; NaCl / 2 h / 150 °C
3: 75 percent / Et3N / 1 h / 20 °C
View Scheme
sennidin B
517-44-2

sennidin B

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chromium (VI)-oxide; acetic acid
2: sulfuric acid
View Scheme
(+)-4,5,4',5'-tetrahydroxy-10,10'-dioxo-9,10,9',10'-tetrahydro-[9,9']bianthryl-2,2'-dicarboxylic acid
517-44-2, 641-12-3, 57762-62-6, 67479-20-3, 98461-42-8

(+)-4,5,4',5'-tetrahydroxy-10,10'-dioxo-9,10,9',10'-tetrahydro-[9,9']bianthryl-2,2'-dicarboxylic acid

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chromium (VI)-oxide; acetic acid
2: sulfuric acid
View Scheme
C6H15N*C19H12O8
1418885-46-7

C6H15N*C19H12O8

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With hydrogenchloride In water; acetone
With hydrogenchloride In water; butanone pH=1;
triacetyl aloe-emodin
25395-11-3

triacetyl aloe-emodin

diacetylrhein
13739-02-1

diacetylrhein

potassium salt of diacerein
112118-18-0

potassium salt of diacerein

pyrographite
7440-44-0

pyrographite

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
In ethanol; water
acetic anhydride
108-24-7

acetic anhydride

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid

1,8-dibenzyloxy-9,10-anthraquinone-3-carboxylic acid

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
iron(III) chloride at 65℃; for 1.5h;
iron(III) chloride at 65℃; for 1.5h;
potassium salt of diacerein
112118-18-0

potassium salt of diacerein

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
With sulfuric acid In ethanol; water; acetone pH=4.5 - 5;
1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione
481-72-1

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 30 °C
2: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 4.5 h / 5 - 25 °C
3: sulfuric acid / 3 h / 5 - 35 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1-methyl-pyrrolidin-2-one / 2 h / 70 °C
2: triethylamine / dichloromethane / 1.4 h / 15 - 20 °C
3: sodium chlorite; sodium dihydrogenphosphate dihydrate; water / dimethyl sulfoxide; acetone / 9 h
View Scheme
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1-methyl-pyrrolidin-2-one / 2 h / 70 °C
2: triethylamine / dichloromethane / 1.4 h / 15 - 20 °C
3: sodium chlorite; sodium dihydrogenphosphate dihydrate; water / dimethyl sulfoxide; acetone / 9 h
View Scheme
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
154658-30-7

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

diacetylrhein
13739-02-1

diacetylrhein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1.4 h / 15 - 20 °C
2: sodium chlorite; sodium dihydrogenphosphate dihydrate; water / dimethyl sulfoxide; acetone / 9 h
View Scheme
diacetylrhein
13739-02-1

diacetylrhein

1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

Conditions
ConditionsYield
With sodium carbonate In water100%
Stage #1: diacetylrhein With water; sodium carbonate
Stage #2: With hydrogenchloride In water pH=2;		100%
With sodium hydroxide In water for 0.5h;60%
diacetylrhein
13739-02-1

diacetylrhein

C19H13NO7

C19H13NO7

Conditions
ConditionsYield
Stage #1: diacetylrhein With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 55℃; for 2h;
Stage #2: With ammonium hydroxide		95%
diacetylrhein
13739-02-1

diacetylrhein

4,5-diacetoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carbonyl chloride
101879-52-1

4,5-diacetoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carbonyl chloride

Conditions
ConditionsYield
With pyridine; thionyl chloride In dichloromethane at 0 - 20℃;92%
With thionyl chloride
With pyridine; thionyl chloride In 1,2-dimethoxyethane at 80℃;
diacetylrhein
13739-02-1

diacetylrhein

berberine hydroxide
117-74-8

berberine hydroxide

C19H11O8(1-)*C20H18NO4(1+)

C19H11O8(1-)*C20H18NO4(1+)

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 60 - 70℃; pH=7 - 8;89%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate

α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(2-methoxyphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(2-methoxyphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		82%
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol at 20℃; for 0.0833333h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol for 0.0833333h;
Stage #3: α-O,O'-diethyl amino(2-methoxyphenyl)methylphosphonate In methanol; N,N-dimethyl-formamide at 35℃; for 4h;		82%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(naphth-1-yl)methylphosphonate

α-O,O'-diethyl amino(naphth-1-yl)methylphosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(1-naphthyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(1-naphthyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol In butan-1-ol at 20℃; for 0.0833333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In butan-1-ol for 0.1h;
Stage #3: α-O,O'-diethyl amino(naphth-1-yl)methylphosphonate In butan-1-ol at 50℃; for 4h;		82%
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(naphth-1-yl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
diacetylrhein
13739-02-1

diacetylrhein

diethyl [amino(4-methylphenyl)methyl]phosphonate
112579-84-7

diethyl [amino(4-methylphenyl)methyl]phosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-methylphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-methylphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: diethyl [amino(4-methylphenyl)methyl]phosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		81%
Stage #1: diacetylrhein With benzotriazol-1-ol In chloroform at 20℃; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform
Stage #3: diethyl [amino(4-methylphenyl)methyl]phosphonate In chloroform at 20℃; for 4h;		81%
diethyl 1-aminophenylmethylphosphonate
16814-08-7, 42077-95-2, 42077-97-4

diethyl 1-aminophenylmethylphosphonate

diacetylrhein
13739-02-1

diacetylrhein

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](phenyl)methyl}phosphonate

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](phenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol at 20℃; for 0.166667h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol for 0.0833333h;
Stage #3: diethyl 1-aminophenylmethylphosphonate In methanol at 20℃; for 4h;		81%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate
1005517-85-0

α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](3-fluorophenyl)methyl}phosphonate

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](3-fluorophenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol at 20℃; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol
Stage #3: α-O,O'-diethyl amino(3-fluorophenyl)methylphosphonate In methanol at 10℃; for 5h;		81%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(2-fluorophenyl)methylphosphonate
181259-90-5

α-O,O'-diethyl amino(2-fluorophenyl)methylphosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(2-fluorophenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(2-fluorophenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(2-fluorophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In ethyl acetate at 20℃; for 0.0833333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate for 0.216667h;
Stage #3: α-O,O'-diethyl amino(2-fluorophenyl)methylphosphonate In ethyl acetate at 20℃; for 4h;		80%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(2-chlorophenyl)methylphosphonate
189180-18-5

α-O,O'-diethyl amino(2-chlorophenyl)methylphosphonate

8-acetyloxy-3-({[(2-chlorophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(2-chlorophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(2-chlorophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.1h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.0833333h;
Stage #3: α-O,O'-diethyl amino(2-chlorophenyl)methylphosphonate In ethyl acetate; N,N-dimethyl-formamide at 20℃; for 4h;		80%
diacetylrhein
13739-02-1

diacetylrhein

diethyl 1-amino(p-chlorophenyl)methylphosphonate
110480-88-1, 110480-89-2, 111408-39-0, 112564-58-6

diethyl 1-amino(p-chlorophenyl)methylphosphonate

8-acetyloxy-3-({[(4-chlorophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(4-chlorophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: diethyl 1-amino(p-chlorophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol; ethyl acetate at 20℃; for 0.0833333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol; ethyl acetate for 0.0833333h;
Stage #3: diethyl 1-amino(p-chlorophenyl)methylphosphonate In methanol; ethyl acetate at 20℃; for 3.5h;		80%
diacetylrhein
13739-02-1

diacetylrhein

[Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester
189180-13-0

[Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester

8-acetyloxy-3-({[(4-bromophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(4-bromophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In dimethyl sulfoxide at 20℃; for 0.166667h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide for 0.166667h;
Stage #3: [Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester In dimethyl sulfoxide at 20℃; for 4h;		80%
diacetylrhein
13739-02-1

diacetylrhein

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate
110470-34-3, 110548-53-3, 110548-54-4, 112564-56-4

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-methoxyphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-methoxyphenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In dimethyl sulfoxide at 20℃; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide
Stage #3: diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate In dimethyl sulfoxide at 60℃; for 3h;		80%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(anthracen-1-yl)methylphosphonate

α-O,O'-diethyl amino(anthracen-1-yl)methylphosphonate

8-acetyloxy-3-({[anthracen-1-yl(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[anthracen-1-yl(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(anthracen-1-yl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		80%
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol at 20℃;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol
Stage #3: α-O,O'-diethyl amino(anthracen-1-yl)methylphosphonate In methanol at 20℃; for 5h;		80%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(4-fluorophenyl)methylphosphonate
135473-59-5

α-O,O'-diethyl amino(4-fluorophenyl)methylphosphonate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-fluorophenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(diethoxyphosphoryl)(4-fluorophenyl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(4-fluorophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		79%
Stage #1: diacetylrhein With benzotriazol-1-ol In dichloromethane; chloroform at 20℃; for 0.133333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; chloroform for 0.05h;
Stage #3: α-O,O'-diethyl amino(4-fluorophenyl)methylphosphonate In dichloromethane; chloroform at 20℃; for 4.5h;		79%
diacetylrhein
13739-02-1

diacetylrhein

α-O,O'-diethyl amino(2-bromophenyl)methylphosphonate

α-O,O'-diethyl amino(2-bromophenyl)methylphosphonate

8-acetyloxy-3-({[(2-bromophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

8-acetyloxy-3-({[(2-bromophenyl)(diethoxyphosphoryl)methyl]amino}carbonyl)-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0℃; for 0.25h;
Stage #2: α-O,O'-diethyl amino(2-bromophenyl)methylphosphonate In dimethyl sulfoxide at 0 - 20℃; for 10h;		79%
Stage #1: diacetylrhein With benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.216667h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.216667h;
Stage #3: α-O,O'-diethyl amino(2-bromophenyl)methylphosphonate In N,N-dimethyl-formamide at 20℃; for 4h;		79%
α-O,O'-diethyl amino(3-bromophenyl)methylphosphonate

α-O,O'-diethyl amino(3-bromophenyl)methylphosphonate

diacetylrhein
13739-02-1

diacetylrhein

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](3-bromophenyl)methyl}phosphonate

O,O'-diethyl {[2-(4,5-diacetyl-9,10-dioxo-9,10-dihydroanthrylamino)acetamido](3-bromophenyl)methyl}phosphonate

Conditions
ConditionsYield
Stage #1: diacetylrhein With benzotriazol-1-ol In methanol at 20℃; for 0.166667h; Cooling with ice;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In methanol for 0.0833333h;
Stage #3: α-O,O'-diethyl amino(3-bromophenyl)methylphosphonate In methanol at 20℃; for 4h;		79%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

diacetylrhein
13739-02-1

diacetylrhein

3-((4-nitrobenzyloxy)carbonyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl diacetate
1400681-59-5

3-((4-nitrobenzyloxy)carbonyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl diacetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h;
Stage #2: 4-nitrobenzyl chloride In dichloromethane for 0.75h; Inert atmosphere;		78.3%
thymol
89-83-8

thymol

diacetylrhein
13739-02-1

diacetylrhein

C29H24O8
1416791-09-7

C29H24O8

Conditions
ConditionsYield
Stage #1: thymol; diacetylrhein With pyridine; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide at 20℃; for 72h;
Stage #2: With acetic acid at 0 - 5℃;		73.54%
pyrrolidine
123-75-1

pyrrolidine

diacetylrhein
13739-02-1

diacetylrhein

9,10-dioxo-3-(pyrrolidine-1-carbonyl)-9,10-dihydroanthracene-1,8-diyl diacetate
1400681-55-1

9,10-dioxo-3-(pyrrolidine-1-carbonyl)-9,10-dihydroanthracene-1,8-diyl diacetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h;
Stage #2: pyrrolidine In dichloromethane for 0.75h; Inert atmosphere;		56.9%
diacetylrhein
13739-02-1

diacetylrhein

Cyclopentamine
1003-03-8

Cyclopentamine

3-(cyclopentylcarbamoyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl diacetate
1400681-57-3

3-(cyclopentylcarbamoyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl diacetate

Conditions
ConditionsYield
Stage #1: diacetylrhein With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h;
Stage #2: Cyclopentamine In dichloromethane for 0.75h; Inert atmosphere;		53%
diazomethane
186581-53-3, 908094-01-9

diazomethane

diacetylrhein
13739-02-1

diacetylrhein

4,5-diacetoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester
13739-04-3

4,5-diacetoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With diethyl ether
diazomethane
186581-53-3, 908094-01-9

diazomethane

diacetylrhein
13739-02-1

diacetylrhein

acetic anhydride
108-24-7

acetic anhydride

4,5,9-triacetoxy-anthracene-2-carboxylic acid methyl ester

4,5,9-triacetoxy-anthracene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
...Expand
methanol
67-56-1

methanol

diacetylrhein
13739-02-1

diacetylrhein

Rhein methyl ester
6155-37-9

Rhein methyl ester

Conditions
ConditionsYield
With sulfuric acid
ethanol
64-17-5

ethanol

diacetylrhein
13739-02-1

diacetylrhein

Ethyl 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate
109650-18-2

Ethyl 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylate

Conditions
ConditionsYield
With sulfuric acid
diacetylrhein
13739-02-1

diacetylrhein

4,5,9-trihydroxy-anthracene-2-carboxylic acid

4,5,9-trihydroxy-anthracene-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride

Diacerein Chemical Properties

Molecular structure of Diacerein (CAS NO.13739-02-1) is:

Product Name: Diacerein
CAS Registry Number: 13739-02-1
IUPAC Name: 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
Molecular Weight: 368.29378 [g/mol]
Molecular Formula: C19H12O8
XLogP3-AA: 1.9
H-Bond Donor: 1
H-Bond Acceptor: 8 
EINECS: 237-310-2
Melting Point: 217-218 °C
Surface Tension: 65.7 dyne/cm
Density: 1.491 g/cm3
Flash Point: 231.8 °C
Enthalpy of Vaporization: 98.15 kJ/mol
Boiling Point: 631.5 °C at 760 mmHg
Vapour Pressure: 8.17E-17 mmHg at 25°C
Product Categories: Miscellaneous Biochemicals;Aromatics Compounds;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals

Diacerein Uses

 Diacerein (CAS NO.13739-02-1) is a drug used in the treatment of osteoarthritis.

Diacerein Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
 R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany : 3
RTECS: CB8781000

Diacerein Specification

 Diacerein , its cas register number is 13739-02-1. It also can be called 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo- (9CI) ; 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, diacetate ; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate ; Diacerein [INN] ; Diacetylrhein ; 1,8-Diacetoxyanthraquinone-3-carboxylic acid ; 4,5-Diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure . It is a yellow crystalline solid.

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