Basic information
- Standard SMILES
Oc1cccc2[nH]ccc12- InChIKey
NLMQHXUGJIAKTH-UHFFFAOYSA-N- Molecular formula
- C8H7NO
- Average molar mass
- 133.15 g/mol
- Monoisotopic mass
- 133.05276384
Overview
4-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole substituted by a hydroxy group at position 4. It is a member of phenols and a member of hydroxyindoles.
Names & identifiers
- Preferred name
- 1H-indol-4-ol
- IUPAC
- 1H-indol-4-ol
- English name
- 4-Hydroxyindole
- Molecular formula
- C8H7NO
- Molecular weight
- 133.15
Names & synonyms
4-Hydroxyindole2380-94-11H-Indol-4-olDTXSID30576961W4VD9085VDTXCID4031485CHEBI:24702RefChem:99330219-177-24-IndololIndol-4-ol4-hydroxy-1h-indole
Show more names
4-Hdroxyindole1H-INDOLE-4-OL4-HydroxyindoL4-Hydroxxyindole4-Hydroxylndole
MFCD00005667UNII-1W4VD9085V4-Hydroxyindole, 99%EINECS 219-177-24-HYDROXYINDOLE [USP-RS]STK802156CCG-214548AC-5462
Database identifiers
- CAS
2380-94-1- PubChem CID
- 75421
- DTXSID
DTXSID3057696- ChEMBL
CHEMBL446571- ChEBI
CHEBI:24702- UNII
- 1W4VD9085V
- EC Number
- 219-177-2
- Nikkaji
- J26.871B
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 36 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 126
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Indoles
CosmeticsHair dyeing
Physical DescriptionGrey crystalline solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 97 · 97-99 °C(lit.)
- Boiling point
- 245.66 °C · 245.66°C (rough estimate)
- Density
- 1.1475 · 1.1475 (rough estimate)
- vapor pressure
- 0.019 Pa · 0.019Pa at 25℃
- refractive index
- 1.526 · 1.5260 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.89 · 9.89±0.40(Predicted)
- color
- Dark Yellow to Green-Grey
- Water Solubility
- slightly soluble
- Sensitive
- Air Sensitive
- BRN
- 114905 · 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
- 1.57 at · 1.57 at 25℃
- CAS DataBase Reference
- 2380 · 2380-94-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 1 W4VD9085V · 1W4VD9085V
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- HazardClass
- IRRITANT, KEEP COLD
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (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.
Hazard information
Regulatory Information
Chemical: 1H-Indol-4-ol
Status: Active Update: 10-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/24224
1H-Indol-4-ol: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; [Sigma-Aldrich MSDS] See Indole.
Hazard Classes and CategoriesSkin Irrit. 2 (98%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- hazard_class
- IRRITANT, KEEP COLD
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use ClassificationCosmetics -> Hair dyeing
Applications
Uses4-Hydroxyindole is a Pindolol (P468000) impurity, which is a mixed adrenergic blocker and serotonin 5HT1A-receptor antagonist.
General DescriptionGlucouridination of 4-hydroxyindole by human uridine 5′-diphospho-glucuronosyltransferase has been repotrted.
Preparation methods
PreparationSynthesis 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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 4-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole substituted by a hydroxy group at position 4. It is a member of phenols and a member of hydroxyindoles.
Related reactions
152 records
Linked notes
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