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5-Hydroxyindole
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Name

5-Hydroxyindole

 EINECS 217-782-6
CAS No. 1953-54-4 Density 1.327 g/cm3
PSA 36.02000 LogP 1.87350
Solubility N/A Melting Point 107-108 °C
Formula C8H7NO Boiling Point 343.2 °C at 760 mmHg
Molecular Weight 133.15 Flash Point 161.4 °C
Transport Information N/A Appearance beige to brown crystalline needles or powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1953-54-4 (5-Hydroxyindole) Hazard Symbols IrritantXi
Synonyms

5-21-03-00018 (Beilstein Handbook Reference);Hydroxy-5 indole [French];Hydroxy-5 indole [French];Hydroxy-5 indole;INDOL-5-OL;1H-Indol-5-ol;5-Hydroxy-1H-indole;1H-Indol-5-ol (9CI);5-Hydroxy-indole;5-Hydroxy indole;

Article Data 44

5-Hydroxyindole Synthetic route

153805-85-7

1-[(E)-2-(5-benzyloxy-2-nitrophenyl)vinyl]pyrrolidine

A

1953-54-4

indol-5-ol

B

1215-59-4

5-benzyloxy-1H-indole

Conditions
ConditionsYield
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 9h;A 1%
B 99%
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 15h;A 3%
B 96%
With hydrogen; 5% rhodium-on-charcoal; nickel(II) nitrate In tetrahydrofuran; water at 20℃; for 23h;A 0.4%
B 93%
144104-59-6

1H-indole-5-boronic acid

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With water; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry;91%
With C11H12ClNOPtS2; triethylamine In N,N-dimethyl-formamide at 20℃; Irradiation;48%
With Oxone; potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 70℃; for 1h; chemoselective reaction;
1215-59-4

5-benzyloxy-1H-indole

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In ethanol Ambient temperature;90%
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave;90%
With palladium on activated charcoal; ethyl acetate Hydrogenation;
80937-33-3

oxygen

144104-59-6

1H-indole-5-boronic acid

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;84%
153969-91-6

5-(prop-2-ynynloxy)indole

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With palladium on activated charcoal; ethanolamine In water at 80℃; Inert atmosphere;77%
1006-94-6

5-methoxylindole

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux;71%
With aluminium trichloride; benzene
With trimethylammonium heptachlorodialuminate In dichloromethane Heating;
15566-30-0

5-benzyloxy-2-nitrophenylacetonitrile

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature;70%

C8H7NO

1953-54-4

indol-5-ol

Conditions
ConditionsYield
With silver nitrate In dichloromethane at 20℃; for 1.5h;64%

methyl (4S,6R)-6-(5-hydroxy-1H-indol-3-yl)-7-hydroxy-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxylate

A

1953-54-4

indol-5-ol

B

methyl (S)-7-hydroxy-3,4-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylate

Conditions
ConditionsYield
In methanol for 10h; Reflux;A 53%
B 61%
172078-33-0

2,3-Dihydro-1H-indol-5-ol

98-95-3

nitrobenzene

A

1953-54-4

indol-5-ol

B

62-53-3

aniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 57%
B 60%

5-Hydroxyindole Specification

The IUPAC name of 5-Hydroxyindole is 1H-indol-5-ol. With the CAS registry number 1953-54-4, it is also named as 5-Hydroxy-1H-indole. The product's categories are Blocks; Indoles Oxindoles; Indole Derivative; Indoles and Derivatives; Pharmacetical; Indole; Indoles; Simple Indoles. Besides, it is beige to brown crystalline needles or powder, which should be stored at 0-6 °C. In addition, its molecular formula is C8H7NO and molecular weight is 133.15.

The other characteristics of this product can be summarized as: (1)EINECS: 217-782-6; (2)ACD/LogP: 0.97; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.97; (5)ACD/LogD (pH 7.4): 0.97; (6)ACD/BCF (pH 5.5): 3.22; (7)ACD/BCF (pH 7.4): 3.21; (8)ACD/KOC (pH 5.5): 80.3; (9)ACD/KOC (pH 7.4): 80.25; (10)#H bond acceptors: 2; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.739; (14)Molar Refractivity: 40.41 cm3; (15)Molar Volume: 100.3 cm3; (16)Surface Tension: 65.8 dyne/cm; (17)Density: 1.327 g/cm3; (18)Flash Point: 161.4 °C; (19)Melting Point: 107-108 °C; (20)Water Solubility: 3.83e+04 mg/l at 25 °c; (21)Enthalpy of Vaporization: 61.03 kJ/mol; (22)Boiling Point: 343.2 °C at 760 mmHg; (23)Vapour Pressure: 3.61E-05 mmHg at 25 °C.

Preparation of 5-Hydroxyindole: this chemical can be prepared by 5-Benzyloxy-indole.



This reaction needs NH4OCOH, 10percent Pd/C and Ethanol at ambient temperature. The yield is 90 %.

Uses of 5-Hydroxyindole: this chemical is used as organic intermediate. Additionally, it can react with Methanesulfonyl chloride to get Methanesulfonic acid 1H-indol-5-yl ester.



This reaction needs CH2Cl2. The yield is 99 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: c1cc2c(cc[nH]2)cc1O
(2)InChI: InChI=1/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
(3)InChIKey: LMIQERWZRIFWNZ-UHFFFAOYAS 

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 453, 1974.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01920,

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