4-Azidosalicylic acid N-hydroxysuccinimide ester

Base Information

• Chemical Name: 4-Azidosalicylic acid N-hydroxysuccinimide ester
• CAS No.: 96602-46-9
• Molecular Formula: C11H8 N4 O5
• Molecular Weight: 276.208
• Hs Code.: 2928009090
• European Community (EC) Number: 691-620-6
• DSSTox Substance ID: DTXSID40242361
• Nikkaji Number: J672.816B
• Wikidata: Q83126031
• Mol file: 96602-46-9.mol

Synonyms:4-azidosalicylic acid N-hydroxysuccinimide ester;N-hydroxysuccinimidyl 4-azidosalicylate;NHS-ASA

Chemical Property of 4-Azidosalicylic acid N-hydroxysuccinimide ester

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 133.66000
• Density: g/cm³
• LogP: 0.94546
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 276.04946937
• Heavy Atom Count: 20
• Complexity: 471

Purity/Quality:

98%Min ^*data from raw suppliers

N-Succinimidyl4-Azidosalicylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=C(C=C(C=C2)N=[N+]=[N-])O
• Uses: 4-azidosalicylic acid N-hydroxysuccinimide ester is a aryl azide which can be used for the photofunctionalization of polymer surfaces.

Technology Process of 4-Azidosalicylic acid N-hydroxysuccinimide ester

There total 4 articles about 4-Azidosalicylic acid N-hydroxysuccinimide 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-carboxy-3-hydroxyphenyl azide (66761-27-1) → succinimide 4-azidosalicylate (96602-46-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 4 ℃;

Reference yield: 53.0%

di(succinimido) carbonate (74124-79-1) + 4-carboxy-3-hydroxyphenyl azide (66761-27-1) → succinimide 4-azidosalicylate (96602-46-9)

Guidance literature:

With pyridine; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1016/0223-5234(90)90121-I

Reference yield:

4-Aminosalicylic acid (65-49-6) → succinimide 4-azidosalicylate (96602-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / 25percent H₂SO₄, NO₂Na, N₃Na / H₂O

2: 53 percent / pyridine / acetonitrile / 16 h / Ambient temperature

With pyridine; sodium azide; sulfuric acid; sodium nitrite; In water; acetonitrile;

DOI:10.1016/0223-5234(90)90121-I

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

4-carboxy-3-hydroxyphenyl azide

di(succinimido) carbonate

4-Aminosalicylic acid

Downstream raw materials:

4-azidosalicoyl-ethylenediamine hydrochloride

[2-(4-azido-2-hydroxy-benzoylamino)-ethyl]-carbamicacid tert-butyl ester