1,2-dimethyl-1H-indol-5-ol

Base Information

• Chemical Name: 1,2-dimethyl-1H-indol-5-ol
• CAS No.: 25888-06-6
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.203
• DSSTox Substance ID: DTXSID70501716
• Wikidata: Q82354248
• Mol file: 25888-06-6.mol

Synonyms:1,2-dimethyl-1H-indol-5-ol;25888-06-6;1H-Indol-5-ol, 1,2-dimethyl-;1,2-dimethyl-5-hydroxyindole;1,2-DIMETHYLINDOL-5-OL;1, 2-dimethylindol-5-ol;SCHEMBL4378545;DTXSID70501716;XROQKUFKUWMFEY-UHFFFAOYSA-N;MFCD02904781;AKOS006279132;CS-16510;CS-0099209;D75992;EN300-253106;Z1198161075

Chemical Property of 1,2-dimethyl-1H-indol-5-ol

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

99.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(N1C)C=CC(=C2)O

Technology Process of 1,2-dimethyl-1H-indol-5-ol

There total 2 articles about 1,2-dimethyl-1H-indol-5-ol 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: 80.0%

5-methoxy-1,2-dimethyl-1H-indole (17591-06-9) → 1,2-Dimethyl-5-hydroxyindole (25888-06-6)

Guidance literature:

With aluminium trichloride; phenylmethanethiol; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)89350-9

Reference yield:

→ 1,2-Dimethyl-5-hydroxyindole (25888-06-6)

Guidance literature:

entspr. Ester 1. Vers. 2. Decarb.;

Reference yield:

1,2-Dimethyl-5-hydroxyindole (25888-06-6) → Bis-(1,2-dimethyl-4-phenylazo-5-methoxyindolyl)methane (78304-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) conc. aq. HCl, NaNO₂, 2.) 5 percent aq. NaOH / 2.) MeOH, 0 deg C, 30 min

2: 1.) aq. NaOH / 1.) dioxane, acetone, 5 deg C, 3 min, 2.) 30 min, r.t.

3: 40 percent / dimethylamine hydrochloride / dioxane; H₂O / 2 h / 60 °C

With hydrogenchloride; sodium hydroxide; N,N-dimethylammonium chloride; sodium nitrite; In 1,4-dioxane; water;

DOI:10.1007/BF00765719

upstream raw materials:

5-methoxy-1,2-dimethyl-1H-indole

Downstream raw materials:

1,2-Dimethyl-3-p-tolylazo-1H-indol-5-ol

4-(4-Chloro-phenylazo)-1,2-dimethyl-1H-indol-5-ol

3-(4-Methoxy-phenylazo)-1,2-dimethyl-1H-indol-5-ol

1,2-Dimethyl-4-phenylazo-1H-indol-5-ol

Refernces

SYNTHESIS AND PROPERTIES OF ARYLAZO-5-HYDROXYINDOLES

10.1007/BF00765719

The research focuses on the synthesis and properties of arylazo-5-hydroxyindoles, with the aim of understanding how the coupling of 1,2-dimethyl-5-hydroxyindoles with aryldiazonium chlorides is influenced by pH, leading to the formation of different compounds. The study demonstrated that in an acetate buffer, 1,2-dimethyl-3-arylazo-5-hydroxyindoles are formed, while in alkaline media, 1,2-dimethyl-4-arylazo-5-hydroxyindoles are obtained. The researchers established the structures of these compounds through NMR spectroscopy and further investigated their antimicrobial activity. The conclusions drawn from the study indicate that while the synthesized compounds showed limited activity against most bacteria, some exhibited good tuberculostatic and fungistatic activity, highlighting their potential as antimicrobial agents.