Hexanedioic acid, bis(pentafluorophenyl) ester

Base Information

• Chemical Name: Hexanedioic acid, bis(pentafluorophenyl) ester
• CAS No.: 83701-40-0
• Molecular Formula: C18H8F10O4
• Molecular Weight: 478.243
• DSSTox Substance ID: DTXSID70454490
• Nikkaji Number: J857.369G
• Wikidata: Q82276041
• Mol file: 83701-40-0.mol

Synonyms:Hexanedioic acid, bis(pentafluorophenyl) ester;83701-40-0;Bis(2,3,4,5,6-pentafluorophenyl) Hexanedioate;Bis(perfluorophenyl) adipate;LCZC1220;SCHEMBL4953772;DTXSID70454490;Hexanedioic acid bis(pentafluorophenyl) ester

Chemical Property of Hexanedioic acid, bis(pentafluorophenyl) ester

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 9
• Exact Mass: 478.02629035
• Heavy Atom Count: 32
• Complexity: 571

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)CC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

Technology Process of Hexanedioic acid, bis(pentafluorophenyl) ester

There total 2 articles about Hexanedioic acid, bis(pentafluorophenyl) ester 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: 85.0%

Adipic acid (124-04-9) + 2,3,4,5,6-pentafluorophenol (771-61-9) → Hexane-1,6-dioic acid bis(pentafluorophenyl) ester (83701-40-0)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/anie.201003424

Reference yield:

Adipic acid (124-04-9) + pentafluorophenyl trifloroacetate (14533-84-7) → Hexane-1,6-dioic acid bis(pentafluorophenyl) ester (83701-40-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm010375a

Reference yield: 79.0%

6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine (1333992-33-8) + Hexane-1,6-dioic acid bis(pentafluorophenyl) ester (83701-40-0) → 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-O-[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]-β-D-adenosine (1333992-40-7)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2011.07.018

upstream raw materials:

Adipic acid

pentafluorophenyl trifloroacetate

2,3,4,5,6-pentafluorophenol

Downstream raw materials:

Adipic acid

2,3,4,5,6-pentafluorophenol

Hexane-1,6-dioic acid bis[(6-phenoxyhexyl)amide]

6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-valyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-O-[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]-β-D-adenosine

Refernces

• 1、 Wang, Jian,Zhang, Ru-Yan,Wang, Ya-Cong,Chen, Xiang-Zhao,Yin, Xu-Guang,Du, Jing-Jing,Lei, Ze,Xin, Ling-Ming,Gao, Xiao-Fei,Liu, Zheng,Guo, Jun. "Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation". supporting information. p. 1934 - 1938. Retrieved 2017/09/13.
• 2、 Dyatkina, Natalia B.,Roberts, Christopher D.,Keicher, Jesse D.,Dai, Yuqin,Nadherny, Joshua P.,Zhang, Wentao,Schmitz, Uli,Kongpachith, Ana,Fung, Kevin,Novikov, Alexander A.,Lou, Lillian,Velligan, Mark,Khorlin, Alexander A.,Chen, Ming S.. "Minor groove DNA binders as antimicrobial agents. 1. Pyrrole tetraamides are potent antibacterials against vancomycin resistant Enteroccoci and methicillin resistant Staphylococcus aureus". . p. 805 - 817. Retrieved 2007/10/03.