1-(Azidomethyl)-4-bromobenzene

Base Information

• Chemical Name: 1-(Azidomethyl)-4-bromobenzene
• CAS No.: 107047-10-9
• Molecular Formula: C7H6BrN3
• Molecular Weight: 212.049
• European Community (EC) Number: 694-421-2
• DSSTox Substance ID: DTXSID20450907
• Nikkaji Number: J258.323B
• Wikidata: Q82270745
• Mol file: 107047-10-9.mol

Synonyms:1-(azidomethyl)-4-bromobenzene;107047-10-9;4-Bromobenzyl azide;4-bromobenzylazide;SCHEMBL13590556;DTXSID20450907;MOKKTDQWMSOCAF-UHFFFAOYSA-N;AKOS009454271;EN300-207146

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

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 210.97451
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CN=[N+]=[N-])Br

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

There total 15 articles about 1-(Azidomethyl)-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: 100.0%

1-bromomethyl-4-bromobenzene (589-15-1) → p-bromobenzylazide (107047-10-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/jacs.6b04061

Reference yield: 98.0%

p-bromobenzyl chloride (589-17-3) → p-bromobenzylazide (107047-10-9)

Guidance literature:

With sodium azide; potassium iodide; In water; acetone; at 20 ℃; for 60h; Inert atmosphere;

DOI:10.1002/anie.201612193

Reference yield: 96.0%

methanesulfonic acid 4-bromo-benzyl ester (237763-11-0) → p-bromobenzylazide (107047-10-9)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 20 ℃; for 15h;

DOI:10.5935/0103-5053.20130121

upstream raw materials:

1-bromomethyl-4-bromobenzene

(4-bromophenyl)methyl 4-methylbenzenesulfonate

4-bromobenzenemethanol

methanesulfonic acid 4-bromo-benzyl ester

Downstream raw materials:

para-bromotoluene

N-(4-bromo-benzyl)-acetamide

methyl 1-(4-bromobenzyl)-1H-1,2,3-triazole-4-carboxylate

4-bromobenzyl isothiocyanate

Refernces

• 1、 Shan, Yuanyuan,Si, Ru,Wang, Jin,Zhang, Qingqing,Zhou, Huaxin,Song, Jie,Zhang, Jie,Chen, Qinhua. "Discovery of novel anti-angiogenesis agents. Part 9: Multiplex inhibitors suppressing compensatory activations of RTKs". . p. 440 - 447. Retrieved 2019.
• 2、 Cilliers, Pieter,Seldon, Ronnett,Smit, Frans J.,Aucamp, Janine,Jordaan, Audrey,Warner, Digby F.,N'Da, David D.. "Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives". . p. 1518 - 1536. Retrieved 2019.
• 3、 Yu, Shichong,Wang, Nan,Chai, Xiaoyun,Wang, Baogang,Cui, Hong,Zhao, Qingjie,Zou, Yan,Sun, Qingyan,Meng, Qingguo,Wu, Qiuye. "Synthesis and antifungal activity of the novel triazole derivatives containing 1,2,3-triazole fragment". . p. 1215 - 1222. Retrieved 2013.
• 4、 Azaroon, Maedeh,Kiasat, Ali Reza. "Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives". . . Retrieved 2018.
• 5、 Kiasat, Ali Reza,Nazari, Simin. "Application of β-cyclodextrin-polyurethane as a stationary microvessel and solid-liquid phase-transfer catalyst: Preparation of benzyl cyanides and azides in water". . p. 102 - 105. Retrieved 2012.
• 6、 Wang, Yinhu,Cong, Chao,Chern Chai, Wern,Dong, Ruiqian,Jia, Li,Song, Di,Zhou, Ziteng,Ma, Shutao. "Synthesis and antibacterial activity of novel 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs". . p. 3872 - 3877. Retrieved 2017.
• 7、 Rodríguez-Hernández, Diego,Barbosa, Luiz C.A.,Demuner, Antonio J.,Nain-Perez, Amalyn,Ferreira, Sebasti?o R.,Fujiwara, Ricardo T.,de Almeida, Raquel M.,Heller, Lucie,Csuk, René. "Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives". . p. 624 - 635. Retrieved 2017.
• 8、 Dangroo, Nisar A.,Singh, Jasvinder,Dar, Alamgir A.,Gupta, Nidhi,Chinthakindi, Praveen K.,Kaul, Anpurna,Khuroo, Mohmmed A.,Sangwan, Payare L.. "Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation". . p. 160 - 169. Retrieved 2016.
• 9、 Ding, Shengtao,Ju, Changhong,Ma, Jiahao,Meng, Congcong,Zhang, Xueyan. "Construction of sequence-defined polytriazoles by IrAAC and CuAAC reactions". . p. 3955 - 3958. Retrieved 2020.
• 10、 Tona, Veronica,De La Torre, Aurélien,Padmanaban, Mohan,Ruider, Stefan,González, Leticia,Maulide, Nuno. "Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides". . p. 8348 - 8351. Retrieved 2016.