Conditions | Yield |
---|---|
With hydrogenchloride for 18h; Heating; | 100% |
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With sodium dithionite-hydrate; sodium hydrogencarbonate In water at 20 - 58℃; for 1h; Inert atmosphere; | 98.1% |
Conditions | Yield |
---|---|
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave; | 95% |
5,6-diacetoxyindole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 0.583333h; | 90% |
With methanol; sodium hydroxide; water at 0℃; Reagens 4: Natriumdithionit; | |
With sodium hydroxide In ethanol |
dopachrome
1H-indole-5,6-diol
Conditions | Yield |
---|---|
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
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water Reagent/catalyst; Solvent; Reflux; | 85.7% |
fumaric acid disodium salt
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With sodium hydroxide; palladium-carbon In water | 76.5% |
(E)-4,5-dihydroxy-2,β-dinitrostyrene
1H-indole-5,6-diol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 56% |
5,6-diacetoxy-2,3-dihydro-indole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 0℃; for 0.833333h; Inert atmosphere; | 54% |
Conditions | Yield |
---|---|
With H2; palladium-carbon In water | 50% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With hydrogenchloride In benzene | 40% |
6-aminodopamine dihydrochloride
A
1H-indole-5,6-diol
B
7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
Conditions | Yield |
---|---|
With air; sodium hydrogencarbonate | A 20% B n/a |
With air; sodium hydrogencarbonate Product distribution; Mechanism; other reagents; | A 20% B n/a |
5,6-(carbonyldioxy)indole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With water at 100℃; for 1h; | 15% |
α-methyldopamine
A
1H-indole-5,6-diol
B
1-(2,4,5-trihydroxyphenyl)-2-aminopropane
Conditions | Yield |
---|---|
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
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate mit Luft; |
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
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
A
1H-indole-5,6-diol
B
4-S-glutathionyl-5,6-dihydroxyindole
Conditions | Yield |
---|---|
0.025 M sodium phosphate buffer, pH=6.8; | A 75 % Chromat. B 10 % Chromat. |
A 75 % Chromat. B 10 % Chromat. |
Conditions | Yield |
---|---|
With hydrogenchloride for 18h; Heating; | 100% |
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With sodium dithionite-hydrate; sodium hydrogencarbonate In water at 20 - 58℃; for 1h; Inert atmosphere; | 98.1% |
Conditions | Yield |
---|---|
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave; | 95% |
5,6-diacetoxyindole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 0.583333h; | 90% |
With methanol; sodium hydroxide; water at 0℃; Reagens 4: Natriumdithionit; | |
With sodium hydroxide In ethanol |
dopachrome
1H-indole-5,6-diol
Conditions | Yield |
---|---|
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
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water Reagent/catalyst; Solvent; Reflux; | 85.7% |
fumaric acid disodium salt
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With sodium hydroxide; palladium-carbon In water | 76.5% |
(E)-4,5-dihydroxy-2,β-dinitrostyrene
1H-indole-5,6-diol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 56% |
5,6-diacetoxy-2,3-dihydro-indole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 0℃; for 0.833333h; Inert atmosphere; | 54% |
Conditions | Yield |
---|---|
With H2; palladium-carbon In water | 50% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With hydrogenchloride In benzene | 40% |
6-aminodopamine dihydrochloride
A
1H-indole-5,6-diol
B
7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
Conditions | Yield |
---|---|
With air; sodium hydrogencarbonate | A 20% B n/a |
With air; sodium hydrogencarbonate Product distribution; Mechanism; other reagents; | A 20% B n/a |
5,6-(carbonyldioxy)indole
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With water at 100℃; for 1h; | 15% |
α-methyldopamine
A
1H-indole-5,6-diol
B
1-(2,4,5-trihydroxyphenyl)-2-aminopropane
Conditions | Yield |
---|---|
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
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate mit Luft; |
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
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
A
1H-indole-5,6-diol
B
4-S-glutathionyl-5,6-dihydroxyindole
Conditions | Yield |
---|---|
0.025 M sodium phosphate buffer, pH=6.8; | A 75 % Chromat. B 10 % Chromat. |
A 75 % Chromat. B 10 % Chromat. |
L-tyrosine
A
indole
B
1H-indole-5,6-diol
C
4,4'-Dihydroxybiphenyl
D
4-Hydroxyphenylpyruvic acid
E
5,6,3-trihydroxyindole
F
anthranilic acid
Conditions | Yield |
---|---|
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
A
1H-indole-5,6-diol
B
levodopa
C
leucodopachromene
D
(2S)-dopachrome
Conditions | Yield |
---|---|
With water; mushroom tyrosinase Rate constant; phosphat buffer, ph 6.8; |
Dopachrome
1H-indole-5,6-diol
Conditions | Yield |
---|---|
Rate constant; | |
With phosphate buffer at 30℃; Mechanism; Rate constant; | 96 % Chromat. |
Conditions | Yield |
---|---|
With zinc diacetate In various solvent(s) Mechanism; Product distribution; Ambient temperature; rearrengament time; | A 91 % Chromat. B 2 % Chromat. |
L-Tryptophan
A
indole
B
1H-indole-5,6-diol
C
4,4'-Dihydroxybiphenyl
D
4-Hydroxyphenylpyruvic acid
E
5,6,3-trihydroxyindole
F
anthranilic acid
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; oxygen; iron(II) sulfate; ascorbic acid In water at 30 - 32℃; for 2h; Product distribution; biomimetic hydroxylation, pH 6.7; |
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With air; tyrosine ase from meal worms at 26 - 30℃; pH 6-6.5; |
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With air; tyrosine ase from meal worms at 26 - 30℃; pH 6-6.5; |
indole
A
1H-indole-5,6-diol
B
indole-2,3-dione
C
anthranilic acid
E
3-hydroxyanthranilic acid
Conditions | Yield |
---|---|
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
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With potassium aluminum sulfate; HAc-NaAc buffer at 15℃; Kinetics; |
1H-indole-5,6-diol
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane | 71% |
1H-indole-5,6-diol
N,O-bis-(trimethylsilyl)-acetamide
Conditions | Yield |
---|---|
In dichloromethane | 71% |
1H-indole-5,6-diol
di(1H-imidazol-2-yl)methanethione
5,6-thiocarbonyldioxy indole
Conditions | Yield |
---|---|
In water; Ethyl propionate; acetone; toluene | 63% |
In di-isopropyl ether; water; acetone; toluene | 63% |
Conditions | Yield |
---|---|
With mushroom tyrosinase for 2h; 0.025 M phosphate buffer; | 48% |
1H-indole-5,6-diol
[1,4]naphthoquinone
2-(5,6-Dihydroxy-1H-indol-3-yl)-[1,4]naphthoquinone
Conditions | Yield |
---|---|
In acetic acid at 5℃; | 42% |
Conditions | Yield |
---|---|
With phosphate buffer In water for 24h; pH=7.4; | 40% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
acetic anhydride
A
5,5',6,6'-tetraacetoxy-2,7'-biindolyl
B
5,5',6,6'-tetraacetoxy-2,4'-biindolyl
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
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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