3-Bromo-9-tosyl-9H-carbazole

Base Information

• Chemical Name: 3-Bromo-9-tosyl-9H-carbazole
• CAS No.: 177775-88-1
• Molecular Formula: C19H14BrNO2S
• Molecular Weight: 400.296
• DSSTox Substance ID: DTXSID401232963
• Nikkaji Number: J3.335.889J
• Mol file: 177775-88-1.mol

Synonyms:3-Bromo-9-tosyl-9H-carbazole;177775-88-1;SCHEMBL8545209;OTYIVOHGSWJZPP-UHFFFAOYSA-N;DTXSID401232963;DS-016616;3-Bromo-9-[(4-methylphenyl)sulfonyl]-9H-carbazole

Chemical Property of 3-Bromo-9-tosyl-9H-carbazole

Chemical Property:

• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 398.99286
• Heavy Atom Count: 24
• Complexity: 552

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C3=C(C=C(C=C3)Br)C4=CC=CC=C42

Technology Process of 3-Bromo-9-tosyl-9H-carbazole

There total 10 articles about 3-Bromo-9-tosyl-9H-carbazole 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%

3-bromo-9H-carbazole (1592-95-6) + p-toluenesulfonyl chloride (98-59-9) → 3-Bromo-9-tosyl-9H-carbazole (177775-88-1)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/acs.orglett.8b02014

Reference yield: 83.0%

C23H27BrN2O3S2 → 3-Bromo-9-tosyl-9H-carbazole (177775-88-1)

Guidance literature:

With silver hexafluoroantimonate; copper diacetate; chloranil; In 1,2-dichloro-ethane; at 80 ℃; for 2.5h; Microwave irradiation;

DOI:10.1039/c8cc03600d

Reference yield:

4-bromo-2-iodoaniline (66416-72-6) → 3-Bromo-9-tosyl-9H-carbazole (177775-88-1)

Guidance literature:

Multi-step reaction with 5 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: dichloromethane / 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C

4: copper(II) sulfate / dichloromethane / 48 h / 20 °C / Inert atmosphere

5: silver hexafluoroantimonate; copper diacetate; chloranil / 1,2-dichloro-ethane / 2.5 h / 80 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; silver hexafluoroantimonate; copper(l) iodide; copper diacetate; chloranil; copper(II) sulfate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/c8cc03600d

upstream raw materials:

9-tosyl-9H-carbazole

potassium carbazole

p-toluenesulfonyl chloride

3-bromo-9H-carbazole

Downstream raw materials:

9-(9H-carbazol-3-yl)-9H-carbazole

3-carbazol-9-yl-9-(p-tolylsulfonyl)carbazole

3,6-Diphenyl-9-tosyl-9H-carbazole