1-(1-Azidoethenyl)-4-bromobenzene

Base Information

• Chemical Name: 1-(1-Azidoethenyl)-4-bromobenzene
• CAS No.: 89108-50-9
• Molecular Formula: C8H6BrN3
• Molecular Weight: 224.06
• DSSTox Substance ID: DTXSID20520250
• Nikkaji Number: J3.314.244G
• Wikidata: Q82384026
• Mol file: 89108-50-9.mol

Synonyms:1-(1-Azidoethenyl)-4-bromobenzene;89108-50-9;Benzene, 1-(1-azidoethenyl)-4-bromo-;DTXSID20520250;1-(1-Azidovinyl)-4-bromobenzene;MFCD30742631;SY318728

Chemical Property of 1-(1-Azidoethenyl)-4-bromobenzene

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.97451
• Heavy Atom Count: 12
• Complexity: 212

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C(C1=CC=C(C=C1)Br)N=[N+]=[N-]

Technology Process of 1-(1-Azidoethenyl)-4-bromobenzene

There total 6 articles about 1-(1-Azidoethenyl)-4-bromobenzene 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: 83.0%

4-bromo-1-ethynylbenzene (766-96-1) → 1-(1-azidovinyl)-4-bromobenzene (89108-50-9)

Guidance literature:

With trimethylsilylazide; water; silver carbonate; In dimethyl sulfoxide; at 80 ℃; Concentration; Time; chemoselective reaction;

DOI:10.1021/ol501661k

Reference yield: 77.0%

1-bromo-4-(1,2-dibromoethyl)benzene (33458-10-5) → 1-(1-azidovinyl)-4-bromobenzene (89108-50-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol5034173

Reference yield:

1-bromo-4-ethenyl-benzene (2039-82-9) → 1-(1-azidovinyl)-4-bromobenzene (89108-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide; Iodine monochloride / acetonitrile / 6.5 h / 20 °C / Cooling

2: potassium tert-butylate / diethyl ether / 5 h / 20 °C

With sodium azide; potassium tert-butylate; Iodine monochloride; In diethyl ether; acetonitrile;

DOI:10.1021/ol3006437

upstream raw materials:

1-bromo-4-ethenyl-benzene

4-bromo-1-ethynylbenzene

1-bromo-4-(1,2-dibromoethyl)benzene

4-bromo-benzaldehyde

Downstream raw materials:

C₂₃H₁₆Br₃N₃O₂

C₂₃H₁₈BrN₃O₂

2-(4-bromophenyl)imidazo[1,2-a]pyridine

2-(4-bromophenyl)imidazo<2,1-a>isoquinoline

Refernces

• 1、 Andresini, Michael,Degannaro, Leonardo,Luisi, Renzo. "A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach". . p. 203 - 209. Retrieved 2021/02/26.
• 2、 Jiang, Huanfeng,Nie, Biao,Ren, Qingyun,Wu, Wanqing,Zeng, Wei,Zhang, Ji,Zhang, Yingjun. "Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides". . . Retrieved 2020/02/25.