4-Bromo-3-phenylsydnone

Base Information

• Chemical Name: 4-Bromo-3-phenylsydnone
• CAS No.: 13183-09-0
• Molecular Formula: C8H5BrN2O2
• Molecular Weight: 241.044
• DSSTox Substance ID: DTXSID20157222
• Wikidata: Q83025372
• Mol file: 13183-09-0.mol

Synonyms:4-BROMO-3-PHENYLSYDNONE;13183-09-0;4-bromo-3-phenyloxadiazol-3-ium-5-olate;Sydnone, 4-bromo-3-phenyl-;4-Bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate;1,2,3-Oxadiazolium, 4-bromo-5-hydroxy-3-phenyl-, inner salt;SCHEMBL15941052;DTXSID20157222;NSC 41404;AKOS005215662

Chemical Property of 4-Bromo-3-phenylsydnone

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.95344
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[N+]2=NOC(=C2Br)[O-]

Technology Process of 4-Bromo-3-phenylsydnone

There total 3 articles about 4-Bromo-3-phenylsydnone 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: 94.0%

3-phenylsydnone (508191-77-3) → 3-phenyl-4-bromosydnone (13183-09-0)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1055/s-2006-926380

Reference yield:

N-Phenylglycine (103-01-5) → 3-phenyl-4-bromosydnone (13183-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 1,3-dibromo-5,5-dimethylhydantoin; NaNO₂; Ac₂O / CH₂Cl₂ / 10 h / 0 - 5 °C

2: 94 percent / 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 2 h / 20 °C

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; acetic anhydride; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-926380

Reference yield:

N-nitroso-N-phenylglycine (6415-68-5) → 3-phenyl-4-bromosydnone (13183-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic anhydride / 3 h / 100 °C

2: acetic acid; N-Bromosuccinimide / 2 h / 20 °C

With N-Bromosuccinimide; acetic anhydride; acetic acid;

DOI:10.1039/c4cc03816a

upstream raw materials:

3-phenylsydnone

N-Phenylglycine

N-nitroso-N-phenylglycine

Downstream raw materials:

3-phenyl-4-trimethylsilanyl-sydnone

3,3'-diphenyl-4,4'-(1-oxo-ethane-1,2-diyl)-bis-sydnone

3,3'-diphenyl-4,4'-oxalyl-bis-sydnone

3-Bromo-2-cyano-3-(N'-dicyanomethylene-N-phenyl-hydrazino)-acrylonitrile