2,5-Dioxopyrrolidin-1-yl 6-azidohexanoate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 6-azidohexanoate
• CAS No.: 866363-70-4
• Molecular Formula: C10H14N4O4
• Molecular Weight: 254.246
• DSSTox Substance ID: DTXSID10469149
• Nikkaji Number: J3.226.324K
• Wikidata: Q82296739
• Mol file: 866363-70-4.mol

Synonyms:866363-70-4;2,5-dioxopyrrolidin-1-yl 6-azidohexanoate;N3-C5-NHS ester;(2,5-dioxopyrrolidin-1-yl) 6-azidohexanoate;MFCD25968077;Hexanoic acid, 6-azido-, 2,5-dioxo-1-pyrrolidinyl ester;1-[(6-Azidohexanoyl)oxy]pyrrolidine-2,5-dione;6-Azidohexanoic acid NHS ester;Azido-Aca-NHS;2,5-Pyrrolidinedione, 1-[(6-azido-1-oxohexyl)oxy]-;LCZC457;SCHEMBL13946653;DTXSID10469149;FVWGCTQOFSJEDB-UHFFFAOYSA-N;AKOS037478135;CS-7066;BP-25454;PD125930;SY034938;HY-126523;CS-0105081;F82471;A1-06739;6-azido-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 6-azidohexanoate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 254.10150494
• Heavy Atom Count: 18
• Complexity: 373

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCN=[N+]=[N-]

Technology Process of 2,5-Dioxopyrrolidin-1-yl 6-azidohexanoate

There total 4 articles about 2,5-Dioxopyrrolidin-1-yl 6-azidohexanoate 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-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 6-azidohexanoic acid (79598-53-1) → 6-azidohexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (866363-70-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1021/jacs.0c05537

Reference yield: 89.0%

6-azidohexanoic acid (79598-53-1) → 6-azidohexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (866363-70-4)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1039/c4ob02094d

Reference yield:

6-bromohexanoic acid (4224-70-8) → 6-azidohexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (866363-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / sodium azide / dimethylformamide / 3 h / 85 °C

2: 80 percent / EDC / CHCl₃; dimethylformamide / 20 °C

With sodium azide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo0505472

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

6-azidohexanoic acid

6-bromohexanoic acid

Downstream raw materials:

O-(9-(2-((N-(6-azidohexanoyl)-N-methylamino)methyl)fluorenyl)methyl) N-phenylcarbamate

Refernces

• 1、 Cutrone, Giovanna,Qiu, Jingwen,Menendez-Miranda, Mario,Casas-Solvas, Juan M.,Ayka?, Ahmet,Li, Xue,Foulkes, Daniel,Moreira-Alvarez, Borja,Encinar, Jorge R.,Ladavière, Catherine,Desma?le, Didier,Vargas-Berenguel, Antonio,Gref, Ruxandra. "Comb-like dextran copolymers: A versatile strategy to coat highly porous MOF nanoparticles with a PEG shell". . . Retrieved 2019.
• 2、 Xu, Yan,Suzuki, Yuta,Ishizuka, Takumi,Xiao, Chao-Da,Liu, Xiao,Hayashi, Tetsuya,Komiyama, Makoto. "Finding a human telomere DNA-RNA hybrid G-quadruplex formed by human telomeric 6-mer RNA and 16-mer DNA using click chemistry: A protective structure for telomere end". . p. 4419 - 4421. Retrieved 2014.
• 3、 Lav, Thanh-Xuan,Lemechko, Pierre,Renard, Estelle,Amiel, Catherine,Langlois, Valérie,Volet, Gisèle. "Development of a new azido-oxazoline monomer for the preparation of amphiphilic graft copolymers by combination of cationic ring-opening polymerization and click chemistry". . p. 1001 - 1008. Retrieved 2013.
• 4、 -. "MULTI-FUNCTIONAL CHIMERIC MOLECULES". Paragraph 0028; 0080. . Retrieved 2021/07/17.