Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-

Base Information

• Chemical Name: Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-
• CAS No.: 824390-92-3
• Molecular Formula: C16H16BrNO2S
• Molecular Weight: 366.279
• DSSTox Substance ID: DTXSID50464931
• Nikkaji Number: J2.134.793K
• Mol file: 824390-92-3.mol

Synonyms:2-(3-bromophenyl)-1-tosylazetidine;824390-92-3;2-(3-bromophenyl)-1-(4-methylbenzenesulfonyl)azetidine;Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-;DTXSID50464931;2-(3-bromophenyl)-N-tosylazetidine

Chemical Property of Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 365.00851
• Heavy Atom Count: 21
• Complexity: 453

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2CCC2C3=CC(=CC=C3)Br

Technology Process of Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-

There total 5 articles about Azetidine, 2-(3-bromophenyl)-1-[(4-methylphenyl)sulfonyl]- 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: 70.0%

4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide (824390-89-8) → 2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine (824390-92-3)

Guidance literature:

4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 12h;

With sodium hydroxide; ethanol; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 2h;

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol048161l

Reference yield:

(E)-N-(3-bromobenzylidene)-4-methylbenzenesulfonamide (863401-20-1) → 2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine (824390-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / tetrahydrofuran; diethyl ether / 12 h / 20 °C

2.1: BH₃*DMS / tetrahydrofuran / 12 h / 20 °C

2.2: aq. NaOH; aq. H₂O₂; EtOH / tetrahydrofuran / 2 h / 20 °C

2.3: 70 percent / DIAD; PPh₃ / tetrahydrofuran / 0 - 20 °C

With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; 1.1: Grignard addition / 2.3: Mitsunobu reaction;

DOI:10.1021/ol048161l

Reference yield:

N-[1-(3-bromo-phenyl)-3-hydroxy-propyl]-4-methyl-benzenesulfonamide (908131-25-9) → 2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine (824390-92-3)

Guidance literature:

With potassium hydroxide; p-toluenesulfonyl chloride; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/j.tetlet.2006.05.058

upstream raw materials:

4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide

N-[1-(3-bromo-phenyl)-3-hydroxy-propyl]-4-methyl-benzenesulfonamide

3-(3-bromo-phenyl)-3-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

(E)-N-(3-bromobenzylidene)-4-methylbenzenesulfonamide

Downstream raw materials:

C₁₈H₁₉BrN₂O₂S

C₂₃H₂₁BrN₂O₂S

N-(3-(3-bromophenyl)-3-chloropropyl)-4-methylbenzenesulfonamide

(E)-3-(3-bromophenyl)-N-tosylprop-2-en-1-amine