Product Name

  • Name

    5,6-Dihydroxyindole

  • EINECS 412-130-9
  • CAS No. 3131-52-0
  • Article Data53
  • CAS DataBase
  • Density 1.51 g/cm3
  • Solubility
  • Melting Point 140 °C (decomp)
  • Formula C8H7NO2
  • Boiling Point 411.2 °C at 760 mmHg
  • Molecular Weight 149.149
  • Flash Point 202.5 °C
  • Transport Information
  • Appearance
  • Safety 22-26-36/37/39-61
  • Risk Codes 22-41-51/53
  • Molecular Structure Molecular Structure of 3131-52-0 (5,6-Dihydroxyindole)
  • Hazard Symbols HarmfulXn; DangerousN
  • Synonyms Indole-5,6-diol(6CI,7CI,8CI);Dopamine lutine;1H-Indole-5,6-diol;
  • PSA 56.25000
  • LogP 1.57910

Synthetic route

5,6-dihydroxy-2-carboxyindole
4790-08-3

5,6-dihydroxy-2-carboxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride for 18h; Heating;100%
C8H7NO2

C8H7NO2

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium dithionite-hydrate; sodium hydrogencarbonate In water at 20 - 58℃; for 1h; Inert atmosphere;98.1%
5,6-dibenzyloxyindole
4790-19-6

5,6-dibenzyloxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave;95%
5,6-diacetoxyindole
15069-79-1

5,6-diacetoxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With potassium carbonate In methanol for 0.583333h;90%
With methanol; sodium hydroxide; water at 0℃; Reagens 4: Natriumdithionit;
With sodium hydroxide In ethanol
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium L-ascorbate In water at 20℃; for 0.75h; Product distribution / selectivity;90%
With sodium chloride In water at 20℃; for 0.75h; Product distribution / selectivity;
5,6-dimethoxyindole
14430-23-0

5,6-dimethoxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water Reagent/catalyst; Solvent; Reflux;85.7%
fumaric acid disodium salt
17013-01-3

fumaric acid disodium salt

5,6-dihydroxyindoline hydrobromide

5,6-dihydroxyindoline hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydroxide; palladium-carbon In water76.5%
(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol under 2585.7 Torr; for 1h;76%
With sodium dithionite; phosphate buffer; zinc(II) sulfate In various solvent(s) at 40℃; for 0.333333h;52%
With hydrogen; palladium on activated charcoal In water under 2585.7 Torr; for 0.75h;50%
ammonium persulfate

ammonium persulfate

5,6-dihydroxyindoline hydrobromide

5,6-dihydroxyindoline hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydroxide In water56%
5,6-diacetoxy-2,3-dihydro-indole
15937-11-8

5,6-diacetoxy-2,3-dihydro-indole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With potassium carbonate In methanol at 0℃; for 0.833333h; Inert atmosphere;54%
CH3 CO2 H

CH3 CO2 H

(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With H2; palladium-carbon In water50%
levodopa
59-92-7

levodopa

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydrogencarbonate; potassium hexacyanoferrate(III) In water for 2.5h;45%
With sodium hydrogencarbonate; potassium hexacyanoferrate(III) In water at 20℃; for 3h; Inert atmosphere;27%
Multi-step reaction with 2 steps
1: 59 percent / air, phosphate buffer pH 7.0 / 2.5 h / 25 °C / mushroom tyrosinase
2: 100 percent / 6 M HCl / 18 h / Heating
View Scheme
Na2 S2 O4

Na2 S2 O4

(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride In benzene40%
6-aminodopamine dihydrochloride
42241-07-6, 54749-74-5

6-aminodopamine dihydrochloride

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
145069-19-8

7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine

Conditions
ConditionsYield
With air; sodium hydrogencarbonateA 20%
B n/a
With air; sodium hydrogencarbonate Product distribution; Mechanism; other reagents;A 20%
B n/a
5,6-(carbonyldioxy)indole
93578-30-4

5,6-(carbonyldioxy)indole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water at 100℃; for 1h;15%
α-methyldopamine
555-64-6

α-methyldopamine

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

1-(2,4,5-trihydroxyphenyl)-2-aminopropane
41241-36-5

1-(2,4,5-trihydroxyphenyl)-2-aminopropane

C

6-nitrodopamine

6-nitrodopamine

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase; sodium nitrite In phosphate buffer at 37℃; pH=7.4; Product distribution; Kinetics; Further Variations:; pH-values; Reagents;A n/a
B 7.2%
C 1.7%
1-(2-amino-4,5-dihydroxyphenyl)-2-ethylamine
38411-80-2

1-(2-amino-4,5-dihydroxyphenyl)-2-ethylamine

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate mit Luft;
6-hydroxydopamine hydrobromide
636-00-0

6-hydroxydopamine hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III)
dopamine
51-61-6

dopamine

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

2,3-dihydro-indolo-5,6-quinone
67992-45-4

2,3-dihydro-indolo-5,6-quinone

Conditions
ConditionsYield
In water-d2 at 24.9℃; for 0.583333h; Rate constant; Mechanism; Irradiation; other sensitizers: methylene blue, rose bengal, fluoresceine; other solvent: H2O.;
With Aβ40 In aq. acetate buffer at 37℃; for 1h; pH=7.4; Reagent/catalyst; pH-value;
glutathion
70-18-8

glutathion

dopachrome

dopachrome

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

4-S-glutathionyl-5,6-dihydroxyindole
103153-88-4

4-S-glutathionyl-5,6-dihydroxyindole

Conditions
ConditionsYield
0.025 M sodium phosphate buffer, pH=6.8;A 75 % Chromat.
B 10 % Chromat.
A 75 % Chromat.
B 10 % Chromat.
5,6-dihydroxy-2-carboxyindole
4790-08-3

5,6-dihydroxy-2-carboxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride for 18h; Heating;100%
C8H7NO2

C8H7NO2

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium dithionite-hydrate; sodium hydrogencarbonate In water at 20 - 58℃; for 1h; Inert atmosphere;98.1%
5,6-dibenzyloxyindole
4790-19-6

5,6-dibenzyloxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave;95%
5,6-diacetoxyindole
15069-79-1

5,6-diacetoxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With potassium carbonate In methanol for 0.583333h;90%
With methanol; sodium hydroxide; water at 0℃; Reagens 4: Natriumdithionit;
With sodium hydroxide In ethanol
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium L-ascorbate In water at 20℃; for 0.75h; Product distribution / selectivity;90%
With sodium chloride In water at 20℃; for 0.75h; Product distribution / selectivity;
5,6-dimethoxyindole
14430-23-0

5,6-dimethoxyindole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water Reagent/catalyst; Solvent; Reflux;85.7%
fumaric acid disodium salt
17013-01-3

fumaric acid disodium salt

5,6-dihydroxyindoline hydrobromide

5,6-dihydroxyindoline hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydroxide; palladium-carbon In water76.5%
(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol under 2585.7 Torr; for 1h;76%
With sodium dithionite; phosphate buffer; zinc(II) sulfate In various solvent(s) at 40℃; for 0.333333h;52%
With hydrogen; palladium on activated charcoal In water under 2585.7 Torr; for 0.75h;50%
ammonium persulfate

ammonium persulfate

5,6-dihydroxyindoline hydrobromide

5,6-dihydroxyindoline hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydroxide In water56%
5,6-diacetoxy-2,3-dihydro-indole
15937-11-8

5,6-diacetoxy-2,3-dihydro-indole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With potassium carbonate In methanol at 0℃; for 0.833333h; Inert atmosphere;54%
CH3 CO2 H

CH3 CO2 H

(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With H2; palladium-carbon In water50%
levodopa
59-92-7

levodopa

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With sodium hydrogencarbonate; potassium hexacyanoferrate(III) In water for 2.5h;45%
With sodium hydrogencarbonate; potassium hexacyanoferrate(III) In water at 20℃; for 3h; Inert atmosphere;27%
Multi-step reaction with 2 steps
1: 59 percent / air, phosphate buffer pH 7.0 / 2.5 h / 25 °C / mushroom tyrosinase
2: 100 percent / 6 M HCl / 18 h / Heating
View Scheme
Na2 S2 O4

Na2 S2 O4

(E)-4,5-dihydroxy-2,β-dinitrostyrene
96806-57-4

(E)-4,5-dihydroxy-2,β-dinitrostyrene

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With hydrogenchloride In benzene40%
6-aminodopamine dihydrochloride
42241-07-6, 54749-74-5

6-aminodopamine dihydrochloride

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
145069-19-8

7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine

Conditions
ConditionsYield
With air; sodium hydrogencarbonateA 20%
B n/a
With air; sodium hydrogencarbonate Product distribution; Mechanism; other reagents;A 20%
B n/a
5,6-(carbonyldioxy)indole
93578-30-4

5,6-(carbonyldioxy)indole

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water at 100℃; for 1h;15%
α-methyldopamine
555-64-6

α-methyldopamine

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

1-(2,4,5-trihydroxyphenyl)-2-aminopropane
41241-36-5

1-(2,4,5-trihydroxyphenyl)-2-aminopropane

C

6-nitrodopamine

6-nitrodopamine

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase; sodium nitrite In phosphate buffer at 37℃; pH=7.4; Product distribution; Kinetics; Further Variations:; pH-values; Reagents;A n/a
B 7.2%
C 1.7%
1-(2-amino-4,5-dihydroxyphenyl)-2-ethylamine
38411-80-2

1-(2-amino-4,5-dihydroxyphenyl)-2-ethylamine

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate mit Luft;
6-hydroxydopamine hydrobromide
636-00-0

6-hydroxydopamine hydrobromide

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III)
dopamine
51-61-6

dopamine

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

2,3-dihydro-indolo-5,6-quinone
67992-45-4

2,3-dihydro-indolo-5,6-quinone

Conditions
ConditionsYield
In water-d2 at 24.9℃; for 0.583333h; Rate constant; Mechanism; Irradiation; other sensitizers: methylene blue, rose bengal, fluoresceine; other solvent: H2O.;
With Aβ40 In aq. acetate buffer at 37℃; for 1h; pH=7.4; Reagent/catalyst; pH-value;
glutathion
70-18-8

glutathion

dopachrome

dopachrome

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

4-S-glutathionyl-5,6-dihydroxyindole
103153-88-4

4-S-glutathionyl-5,6-dihydroxyindole

Conditions
ConditionsYield
0.025 M sodium phosphate buffer, pH=6.8;A 75 % Chromat.
B 10 % Chromat.
A 75 % Chromat.
B 10 % Chromat.
L-tyrosine
60-18-4

L-tyrosine

A

indole
120-72-9

indole

B

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

C

4,4'-Dihydroxybiphenyl
92-88-6

4,4'-Dihydroxybiphenyl

D

4-Hydroxyphenylpyruvic acid
156-39-8

4-Hydroxyphenylpyruvic acid

E

5,6,3-trihydroxyindole
3569-19-5

5,6,3-trihydroxyindole

F

anthranilic acid
118-92-3

anthranilic acid

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; oxygen; iron(II) sulfate; ascorbic acid In water at 30 - 32℃; for 2h; Product distribution; biomimetic hydroxylation, pH 6.7;
L-tyrosine
60-18-4

L-tyrosine

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

levodopa
59-92-7

levodopa

C

leucodopachromene
18766-67-1

leucodopachromene

D

(2S)-dopachrome
3571-34-4, 89762-39-0

(2S)-dopachrome

Conditions
ConditionsYield
With water; mushroom tyrosinase Rate constant; phosphat buffer, ph 6.8;
Dopachrome
13520-94-0

Dopachrome

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
Rate constant;
With phosphate buffer at 30℃; Mechanism; Rate constant;96 % Chromat.
Dopachrome
13520-94-0

Dopachrome

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

5,6-dihydroxy-2-carboxyindole
4790-08-3

5,6-dihydroxy-2-carboxyindole

Conditions
ConditionsYield
With zinc diacetate In various solvent(s) Mechanism; Product distribution; Ambient temperature; rearrengament time;A 91 % Chromat.
B 2 % Chromat.
L-Tryptophan
73-22-3

L-Tryptophan

A

indole
120-72-9

indole

B

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

C

4,4'-Dihydroxybiphenyl
92-88-6

4,4'-Dihydroxybiphenyl

D

4-Hydroxyphenylpyruvic acid
156-39-8

4-Hydroxyphenylpyruvic acid

E

5,6,3-trihydroxyindole
3569-19-5

5,6,3-trihydroxyindole

F

anthranilic acid
118-92-3

anthranilic acid

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; oxygen; iron(II) sulfate; ascorbic acid In water at 30 - 32℃; for 2h; Product distribution; biomimetic hydroxylation, pH 6.7;
1(-)-tyrosine

1(-)-tyrosine

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With air; tyrosine ase from meal worms at 26 - 30℃; pH 6-6.5;
l(-)-3.4-dioxy-phenylalanine

l(-)-3.4-dioxy-phenylalanine

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With air; tyrosine ase from meal worms at 26 - 30℃; pH 6-6.5;
indole
120-72-9

indole

A

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

B

indole-2,3-dione
91-56-5

indole-2,3-dione

C

anthranilic acid
118-92-3

anthranilic acid

D

3-hydroxy pyrrolle-4,5-dicarboxylic acid

3-hydroxy pyrrolle-4,5-dicarboxylic acid

E

3-hydroxyanthranilic acid
548-93-6

3-hydroxyanthranilic acid

F

melanin

melanin

Conditions
ConditionsYield
With phosphate buffer; ethylenediaminetetraacetic acid; iron(II) sulfate; ascorbic acid In water; acetone at 37℃; for 2h; Product distribution; melanin formation under Udenfriend condition, oxygen atmosphere;
(2S)-dopachrome
3571-34-4, 89762-39-0

(2S)-dopachrome

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

Conditions
ConditionsYield
With potassium aluminum sulfate; HAc-NaAc buffer at 15℃; Kinetics;
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

5,6-bis (trimethylsilyloxy)-indole

5,6-bis (trimethylsilyloxy)-indole

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane71%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

N,O-bis-(trimethylsilyl)-acetamide
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

5,6-bis (trimethylsilyloxy)-indole

5,6-bis (trimethylsilyloxy)-indole

Conditions
ConditionsYield
In dichloromethane71%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

di(1H-imidazol-2-yl)methanethione
88681-68-9

di(1H-imidazol-2-yl)methanethione

5,6-thiocarbonyldioxy indole
113370-16-4

5,6-thiocarbonyldioxy indole

Conditions
ConditionsYield
In water; Ethyl propionate; acetone; toluene63%
In di-isopropyl ether; water; acetone; toluene63%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

glutathion
70-18-8

glutathion

4-S-glutathionyl-5,6-dihydroxyindole
103153-88-4

4-S-glutathionyl-5,6-dihydroxyindole

Conditions
ConditionsYield
With mushroom tyrosinase for 2h; 0.025 M phosphate buffer;48%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-(5,6-Dihydroxy-1H-indol-3-yl)-[1,4]naphthoquinone
112097-20-8

2-(5,6-Dihydroxy-1H-indol-3-yl)-[1,4]naphthoquinone

Conditions
ConditionsYield
In acetic acid at 5℃;42%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

4-[bis-(1H-5,6-dihydroxyindol-2-yl)methyl]-1,2-dihydroxybenzene

4-[bis-(1H-5,6-dihydroxyindol-2-yl)methyl]-1,2-dihydroxybenzene

Conditions
ConditionsYield
With phosphate buffer In water for 24h; pH=7.4;40%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

acetic anhydride
108-24-7

acetic anhydride

A

2,3,7,8,12,13-hexaacetoxydiindolo[3,2-a:3',2'-c]carbazole

2,3,7,8,12,13-hexaacetoxydiindolo[3,2-a:3',2'-c]carbazole

B

2,3,6,7,11,12-hexaacetoxydiindolo[2,3-a:2',3'-c]carbazole

2,3,6,7,11,12-hexaacetoxydiindolo[2,3-a:2',3'-c]carbazole

Conditions
ConditionsYield
Stage #1: 1H-indole-5,6-diol With ammonium persulfate; phosphoric acid In water pH=1.4; Oxidation;
Stage #2: acetic anhydride With pyridine Acetylation;
A 29%
B 19%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

acetic anhydride
108-24-7

acetic anhydride

A

2,3,7,8,12,13-hexaacetoxy-5,10,15-trimethyldiindolo[3,2-a:3',2'-c]carbazole

2,3,7,8,12,13-hexaacetoxy-5,10,15-trimethyldiindolo[3,2-a:3',2'-c]carbazole

B

2,3,6,7,11,12-hexaacetoxy-9,14,15-trimethyldiindolo[2,3-a:2',3'-c]carbazole

2,3,6,7,11,12-hexaacetoxy-9,14,15-trimethyldiindolo[2,3-a:2',3'-c]carbazole

Conditions
ConditionsYield
Stage #1: 1H-indole-5,6-diol With ammonium persulfate; phosphoric acid In water pH=1.4; Oxidation;
Stage #2: acetic anhydride With pyridine Acetylation;
A 26%
B 24%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

acetic anhydride
108-24-7

acetic anhydride

A

5,5',6,6'-tetraacetoxy-2,7'-biindolyl
131248-80-1

5,5',6,6'-tetraacetoxy-2,7'-biindolyl

B

5,5',6,6'-tetraacetoxy-2,4'-biindolyl
131248-81-2

5,5',6,6'-tetraacetoxy-2,4'-biindolyl

Conditions
ConditionsYield
Stage #1: 1H-indole-5,6-diol With dihydrogen peroxide; horseradish peroxidase In phosphate buffer for 0.00694444h; pH=7.0;
Stage #2: acetic anhydride In pyridine at 20℃;
A 10%
B 15%
Stage #1: 1H-indole-5,6-diol With dihydrogen peroxide; horseradish peroxidase In phosphate buffer; acetone pH=7.0;
Stage #2: acetic anhydride In pyridine at 20℃;
A 13%
B 4%
2-thiouracil
141-90-2

2-thiouracil

1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

A

2-(5,6-Dihydroxy-1H-indol-2-ylsulfanyl)-3H-pyrimidin-4-one

2-(5,6-Dihydroxy-1H-indol-2-ylsulfanyl)-3H-pyrimidin-4-one

B

2-(5,6-Dihydroxy-1H-indol-3-ylsulfanyl)-3H-pyrimidin-4-one

2-(5,6-Dihydroxy-1H-indol-3-ylsulfanyl)-3H-pyrimidin-4-one

C

5,5',6,6'-tetrahydroxy-2,2'-bis[(4-hydroxypyrimidin-2-yl)thio]-4,4'-biindolyl

5,5',6,6'-tetrahydroxy-2,2'-bis[(4-hydroxypyrimidin-2-yl)thio]-4,4'-biindolyl

D

5,5',5",6,6',6"-hexahydroxy-2',3-bis[(4-hydroxypyrimidin-2-yl)thio]4,7':4',4"-terindolyl

5,5',5",6,6',6"-hexahydroxy-2',3-bis[(4-hydroxypyrimidin-2-yl)thio]4,7':4',4"-terindolyl

Conditions
ConditionsYield
With phosphate buffer pH 7.0; mushroom tyrosinase for 0.833333h; Product distribution; Mechanism; other melanin precursor;A 4%
B 5%
C 2%
D 9%
With phosphate buffer pH 7.0; mushroom tyrosinase for 0.833333h;A 4%
B 5%
C 2%
D 9%
1H-indole-5,6-diol
3131-52-0

1H-indole-5,6-diol

acetic anhydride
108-24-7

acetic anhydride

A

5,6-diacetoxy-N-acetyl-2-(5',6'-diacetoxyindol-3'-yl)indoline

5,6-diacetoxy-N-acetyl-2-(5',6'-diacetoxyindol-3'-yl)indoline

B

acetic acid 6-acetoxy-3-[2-(4,5-diacetoxy-2-acetylamino-phenyl)-1-(5,6-diacetoxy-1H-indol-3-yl)-ethyl]-1H-indol-5-yl ester

acetic acid 6-acetoxy-3-[2-(4,5-diacetoxy-2-acetylamino-phenyl)-1-(5,6-diacetoxy-1H-indol-3-yl)-ethyl]-1H-indol-5-yl ester

Conditions
ConditionsYield
Stage #1: 1H-indole-5,6-diol With ammonium persulfate; phosphoric acid In water for 0.000277778h; pH=1.4; Oxidation;
Stage #2: acetic anhydride With pyridine Acetylation;
A 9%
B 5%

5,6-Dihydroxyindole Specification

The IUPAC name of this chemical is 1H-Indole-5,6-diol. With the CAS registry number 3131-52-0, it is also named as 5,6-dihydroxyindole. In addition, the molecular formula is C8H7NO2 and the molecular weight is 149.15. What's more, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about 1H-Indole-5,6-diol are: (1)ACD/LogP: 0.37; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.37; (4)ACD/LogD (pH 7.4): 0.37; (5)ACD/BCF (pH 5.5): 1.12; (6)ACD/BCF (pH 7.4): 1.12; (7)ACD/KOC (pH 5.5): 37.78; (8)ACD/KOC (pH 7.4): 37.72; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 23.39 Å2; (13)Index of Refraction: 1.802; (14)Molar Refractivity: 42.29 cm3; (15)Molar Volume: 98.7 cm3; (16)Polarizability: 16.76 ×10-24cm3; (17)Surface Tension: 86 dyne/cm; (18)Density: 1.51 g/cm3; (19)Flash Point: 202.5 °C; (20)Enthalpy of Vaporization: 68.95 kJ/mol; (21)Boiling Point: 411.2 °C at 760 mmHg; (22)Vapour Pressure: 2.38E-07 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. And it has risk of serious damage to eyes. Moreover, it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. You should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, you should avoid release to the environment and you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1cc2c(cc1O)ncc2
(2)Std.InChI: InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
(3)Std.InChIKey: SGNZYJXNUURYCH-UHFFFAOYSA-N

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