HuagongsheHuagongshe Chemistry Print Report · For research reference only
1H-indol-4-ol
1H-INDOL-4-OL · 4-INDOLOL · 4-Hdroxyindole · 4-HYDROXY-1H-INDOLE · INDOL-4-OL · 1H-INDOLE-4-OL · 4-HydroxyindoL · 4-HYDROXYINDOLE
Identifiers & Physical Properties
| CAS No. | 2380-94-1 |
|---|---|
| Molecular formula | C8H7NO |
| Average molar mass | 133.15 g/mol |
| Monoisotopic mass | 133.05276384 g/mol |
| SMILES | Oc1cccc2[nH]ccc12 |
| InChIKey | NLMQHXUGJIAKTH-UHFFFAOYSA-N |
| PubChem CID | 75421 |
| ChEMBL | CHEMBL446571 |
| ChEBI | CHEBI:24702 |
| EC No. | 219-177-2 |
| DTXSID | DTXSID3057696 |
Chemical & Physical Properties
| XLogP | 2.4 |
|---|---|
| Topological polar surface area | 36 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 126 |
| Chemical classes | Nitrogen Compounds -> Indoles |
| Cosmetics | Hair dyeing |
| Physical Description | Grey crystalline solid[Sigma-Aldrich MSDS] |
| Melting point | 97-99 °C(lit.) |
| Boiling point | 245.66°C (rough estimate) |
| Density | 1.1475 (rough estimate) |
| Vapor pressure | 0.019Pa at 25℃ |
| Refractive index | 1.5260 (estimate) |
| Storage conditions | 0-6°C |
| Solubility | DMSO (Slightly), Methanol (Slightly)slightly soluble |
| Physical state | Solid |
| pKa (acidity coefficient) | 9.89±0.40(Predicted) |
| Color | Dark Yellow to Green-Grey |
| Sensitivity | Air Sensitive |
| BRN | 114905 |
| Cosmetics Ingredients Functions | HAIR DYEING |
| InChI | 1S/C8H7NO/c10-8-3-1-2-7-6(8)4-5-9-7/h1-5,9-10H |
| InChIKey | NLMQHXUGJIAKTH-UHFFFAOYSA-N |
| SMILES | Oc1cccc2[nH]ccc12 |
| LogP (partition coefficient) | 1.57 at 25℃ |
| CAS DataBase Reference | 2380-94-1(CAS DataBase Reference) |
| EWG's Food Scores | 1-3 |
| FDA UNII | 1W4VD9085V |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant |
| Hazard class | IRRITANT, KEEP COLDEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 1H-Indol-4-olStatus: Active Update: 10-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/242241H-Indol-4-ol: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | An irritant[Sigma-Aldrich MSDS] See Indole. |
| Hazard Classes and Categories | Skin Irrit. 2 (98%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| Customs code | 29339900 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-36-37/39 |
| Hazard class | IRRITANT, KEEP COLDEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
Uses
4-Hydroxyindole is a Pindolol (P468000) impurity, which is a mixed adrenergic blocker and serotonin 5HT1A-receptor antagonist.
General Description
Glucouridination of 4-hydroxyindole by human uridine 5′-diphospho-glucuronosyltransferase has been repotrted.
Preparation & Synthesis
Preparation
Synthesis of 4-hydroxyindole: Using resorcinol as raw material, 4-oxotetrahydrocoumarone carboxylic acid is prepared by isomerization, catalytic hydrogenation, and cyclization with ethyl bromopyruvate. It was added to methanol solution saturated with ammonia, and the reaction was heated in an autoclave to generate 4-oxotetrahydroindole. Finally, 4-hydroxyindole is obtained by dehydrogenation and isomerization.