6-methyl-9H-carbazol-3-ol

Base Information

• Chemical Name: 6-methyl-9H-carbazol-3-ol
• CAS No.: 5257-08-9
• Molecular Formula: C13H11NO
• Molecular Weight: 197.236
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID601035153
• Nikkaji Number: J2.373.908I
• Wikidata: Q104400566
• Metabolomics Workbench ID: 127585
• ChEMBL ID: CHEMBL2260670
• Mol file: 5257-08-9.mol

Synonyms:glycozolinol

Chemical Property of 6-methyl-9H-carbazol-3-ol

Chemical Property:

• PSA: 36.02000
• LogP: 3.33510
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 197.084063974
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

98%Min ^*data from raw suppliers

Glycozolinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC3=C2C=C(C=C3)O

Technology Process of 6-methyl-9H-carbazol-3-ol

There total 21 articles about 6-methyl-9H-carbazol-3-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: 97.0%

glycozoline (5234-30-0) → 3-methyl-6-hydroxycarbazol (5257-08-9)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 4h;

DOI:10.1055/s-2007-967984

Reference yield: 54.0%

[5'-(tert-Butyl-dimethyl-silanyloxy)-2'-chloro-5-methyl-biphenyl-2-yl]-carbamic acid tert-butyl ester (151692-24-9) → 3-methyl-6-hydroxycarbazol (5257-08-9)

Guidance literature:

With potassium amide; In ammonia; at -33 ℃; for 3h;

DOI:10.3987/COM-93-6368

Reference yield:

1-bromo-4-methoxy-benzene (104-92-7) → 3-methyl-6-hydroxycarbazol (5257-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / rac-BINAP; Cs₂CO₃ / Pd(OAc)2 / toluene / 144 h / 110 °C

2: 60 percent / Cu(OAc)2 / Pd(OAc)2 / acetic acid / 24 h / 117 °C

3: 97 percent / boron tribromide / CH₂Cl₂ / 4 h / -78 - 20 °C

With copper diacetate; boron tribromide; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In dichloromethane; acetic acid; toluene; 1: Buchwald-Hartwig amination;

DOI:10.1055/s-2007-967984

upstream raw materials:

6-hydroxy-3-methyl-1,2,3,4-tetrahydrocarbazole

[5'-(tert-Butyl-dimethyl-silanyloxy)-2'-chloro-5-methyl-biphenyl-2-yl]-carbamic acid tert-butyl ester

glycozoline

1-bromo-4-methoxy-benzene

Downstream raw materials:

glycozoline

3-Methyl-9H-carbazole

Refernces

• 1、 Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee. "Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates". supporting information. p. 4759 - 4763. Retrieved 2018/08/24.
• 2、 Forke, Ronny,Krahl, Micha P.,Krause, Tilo,Schlechtingen, Georg,Kn?lker, Hans-Joachim. "Transition metals in organic synthesis, part 82.1 First total synthesis of methyl 6-methoxycarbazole-3-carboxylate, glycomaurrol, the anti-TB active micromeline, and the furo[2,3-c]carbazole alkaloid eustifoline-D". . p. 268 - 272. Retrieved 2007/10/03.