5-Hydroxyindole

Base Information

• Chemical Name: 5-Hydroxyindole
• CAS No.: 1953-54-4
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 2933.99
• European Community (EC) Number: 217-782-6
• NSC Number: 87503
• UNII: 320UN7XZYN
• DSSTox Substance ID: DTXSID00173187
• Nikkaji Number: J41.080B
• Wikidata: Q27073984
• Metabolomics Workbench ID: 133783
• ChEMBL ID: CHEMBL404923
• Mol file: 1953-54-4.mol

Synonyms:1 H-indol-5-ol;5-hydroxyindole;indol-5-ol

Chemical Property of 5-Hydroxyindole

Chemical Property:

• Appearance/Colour: beige to brown crystalline needles or powder
• Vapor Pressure: 3.61E-05mmHg at 25°C
• Melting Point: 107-108 °C
• Refractive Index: 1.739
• Boiling Point: 343.2 °C at 760 mmHg
• PKA: 9.98±0.40(Predicted)
• Flash Point: 161.4 °C
• PSA: 36.02000
• Density: 1.327 g/cm³
• LogP: 1.87350
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: 38g/l
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1O
• Uses: ? ;Reactant for preparation of (oxoimidazolidinyl/oxopyrimidinyl)benzenesulfonates as antitumor agents and tubulin inhibitors1? ;Reactant for preparation of anthranilic acids2? ;Reactant for preparation of indole compounds as dopamine D2 receptor antagonists3? ;Reactant for preparation of naphthalimide- or carbazole-containing human β-adrenoceptor ligands4? ;Reactant for preparation of melanins as nature-inspired radioprotectors5? ;Reactant for preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors6 5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptop han (T894800). 5-Hydroxyindole displayed weak inhibitory activity on human melanoma tyrosinase. 5-Hydroxyindole also showed inhibition of serotonin transport by blood platelets. 5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptophan (T894800). 5-Hydroxyindole displayed weak inhibitory activity on human melanoma tyrosinase. 5-Hydroxyindole also showed inhibition of serotonin transport by blood platelets.

Technology Process of 5-Hydroxyindole

There total 50 articles about 5-Hydroxyindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

1H-indole-5-boronic acid (144104-59-6) → indol-5-ol (1953-54-4)

Guidance literature:

With water; dihydrogen peroxide; In ethanol; at 20 ℃; for 0.0166667h; Green chemistry;

DOI:10.1039/d0ra08580d

Reference yield: 90.0%

5-benzyloxy-1H-indole (1215-59-4) → indol-5-ol (1953-54-4)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In ethanol; Ambient temperature;

DOI:10.1021/jm970460b

Reference yield: 84.0%

oxygen (80937-33-3) + 1H-indole-5-boronic acid (144104-59-6) → indol-5-ol (1953-54-4)

Guidance literature:

With triethanolamine; In water; at 20 ℃; for 18h; Sonication; Irradiation; Green chemistry;

DOI:10.1016/j.tetlet.2020.152010

upstream raw materials:

5-methoxylindole

1H-indol-5-yl acetate

5-hydroxyindole-2-carboxylic acid

5-benzyloxy-1H-indole

Downstream raw materials:

1H-indol-5-yl acetate

5-(2-propenyloxy)indole

1-(2-propenyloxy)indole

L-5-HTP

Refernces

• 1、 Waclawiková, Barbora,Bullock, Amber,Schwalbe, Markus,Aranzamendi, Carmen,Nelemans, Sieger A.,van Dijk, Gertjan,El Aidy, Sahar. "Gut bacteria-derived 5-hydroxyindole is a potent stimulant of intestinal motility via its action on L-type calcium channels". . . Retrieved 2021/02/22.
• 2、 Matsumoto, Makoto,Wada, Kohei,Urakawa, Kazuki,Ishikawa, Hayato. "Diaryliodonium Salt-Mediated Intramolecular C-N Bond Formation Using Boron-Masking N-Hydroxyamides". supporting information. p. 781 - 785. Retrieved 2020/02/04.