N-(4-Bromobenzylidene)-p-toluenesulfonamide

Base Information

• Chemical Name: N-(4-Bromobenzylidene)-p-toluenesulfonamide
• CAS No.: 36176-90-6
• Molecular Formula: C14H12BrNO2S
• Molecular Weight: 338.225
• Hs Code.: 2935009090
• European Community (EC) Number: 695-469-7
• DSSTox Substance ID: DTXSID00407494
• Nikkaji Number: J1.071.213K
• Mol file: 36176-90-6.mol

Synonyms:36176-90-6;N-(4-Bromobenzylidene)-p-toluenesulfonamide;N-[(4-bromophenyl)methylidene]-4-methylbenzenesulfonamide;N-(4-Bromobenzylidene)-4-methylbenzenesulfonamide;SCHEMBL10047313;DTXSID00407494;N-(4-Bromobenzylidene)-4-toluenesulfonamide;N-[(4-Bromophenyl)methylidene]-4-methylbenzene-1-sulfonamide

Chemical Property of N-(4-Bromobenzylidene)-p-toluenesulfonamide

Chemical Property:

• Melting Point: 191-196 °C
• PSA: 54.88000
• LogP: 4.64610
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 336.97721
• Heavy Atom Count: 19
• Complexity: 400

Purity/Quality:

N-(4-Bromobenzylidene)-p-toluenesulfonamide 97% ^*data from reagent suppliers

Safty Information:

• 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: CC1=CC=C(C=C1)S(=O)(=O)N=CC2=CC=C(C=C2)Br

Technology Process of N-(4-Bromobenzylidene)-p-toluenesulfonamide

There total 13 articles about N-(4-Bromobenzylidene)-p-toluenesulfonamide 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: 99.0%

4-bromobenzenemethanol (873-75-6) + toluene-4-sulfonamide (70-55-3) → N-(4-bromobenzylidene)-4-methylbenzenesulfonamide (36176-90-6)

Guidance literature:

With potassium carbonate; In neat (no solvent); at 160 ℃; for 12h; Inert atmosphere; Green chemistry;

DOI:10.1039/c4ra06685e

Reference yield: 98.0%

toluene-4-sulfonamide (70-55-3) + 4-bromo-benzaldehyde (1122-91-4) → N-(4-bromobenzylidene)-4-methylbenzenesulfonamide (36176-90-6)

Guidance literature:

With amberlyst 15; In toluene; for 16h; Heating; Molecular sieve;

DOI:10.1016/j.tetasy.2009.11.020

Reference yield: 89.0%

Tosyl isocyanate (4083-64-1) + 4-bromo-benzaldehyde (1122-91-4) → N-(4-bromobenzylidene)-4-methylbenzenesulfonamide (36176-90-6)

Guidance literature:

at 90 ℃; for 1h;

DOI:10.1021/acs.orglett.5b03686

upstream raw materials:

(2S,3S)-3-(4-Bromo-phenyl)-2-(toluene-4-sulfonyl)-oxaziridine

toluene-4-sulfonamide

4-bromo-benzaldehyde

diphenyl-N-(p-toluenesulfonyl)selenimide

Downstream raw materials:

(2R,3R)-2-(4-Bromo-phenyl)-3-pentafluorophenyl-1-(toluene-4-sulfonyl)-aziridine

(2S,3S)-methyl 3-(4-bromophenyl)-2-(diphenylmethyleneamino)-3-(4-methylphenylsulfonamido)propanoate

(2S,3R)-methyl 3-(4-bromophenyl)-2-(diphenylmethyleneamino)-3-(4-methylphenylsulfonamido)propanoate

C₂₆H₂₈BrNO₆S

Refernces

• 1、 Delost, Michael D.,Njardarson, Jon T.. "Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures". supporting information. p. 6121 - 6125. Retrieved 2021/08/16.
• 2、 Stead, Darren. "The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles". supporting information. . Retrieved 2020/09/04.