4-Azidobenzoyloxysuccinimide

Base Information

• Chemical Name: 4-Azidobenzoyloxysuccinimide
• CAS No.: 53053-08-0
• Molecular Formula: C11H8 N4 O4
• Molecular Weight: 260.209
• Hs Code.: 2928009090
• NSC Number: 329704
• UNII: 8ZXQ80NJ3B
• DSSTox Substance ID: DTXSID40201094
• Nikkaji Number: J749.962K
• Wikidata: Q83074278
• Mol file: 53053-08-0.mol

Synonyms:4-azidobenzoic acid N-hydroxysuccinimide ester;4-azidobenzoyloxysuccinimide;HSAB;hydroxysuccinimidyl-4-azidobenzoate;hydroxysuccinimidyl-p-azidobenzoate;N-hydroxysuccinimidyl-4-azidobenzoate

Chemical Property of 4-Azidobenzoyloxysuccinimide

Chemical Property:

• Melting Point: 171-172°C
• PSA: 113.43000
• LogP: 1.23986
• Storage Temp.: −20°C
• Solubility.: chloroform: 50 mg/mL
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 260.05455475
• Heavy Atom Count: 19
• Complexity: 434

Purity/Quality:

NLT 98% ^*data from raw suppliers

N-Hydroxysuccinimidyl-4-azidobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=CC=C(C=C2)N=[N+]=[N-]
• Description: N-Hydroxysuccinimidyl-4-azidobenzoate is an aryl azide-based, amine- and photoreactive crosslinker.

Technology Process of 4-Azidobenzoyloxysuccinimide

There total 4 articles about 4-Azidobenzoyloxysuccinimide 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) + 4-azidobenzoic acid (6427-66-3) → 4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 23 ℃; for 21h; Inert atmosphere; Darkness;

DOI:10.1039/c8cc09660k

Reference yield: 99.0%

succinimidyl 4-((di(tert-butyl)(4-(dimethylamino)phenyl)phosphanylidene)triazen-1-yl)benzoate → 4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0)

Guidance literature:

With sulfur; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01692

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; sodium nitrite / water

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / -78 - 20 °C

With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

4-azidobenzoic acid

4-amino-benzoic acid

Downstream raw materials:

N-(4-azidobenzoyl)tyrosine

6-<(4-Azidobenzoyl)amino>hexanoic acid

3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

3(R)-[(4(R)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

Refernces

• 1、 Shi, Bingbing,Deng, Yuqing,Zhao, Peng,Li, Xiaoyu. "Selecting a DNA-Encoded Chemical Library against Non-immobilized Proteins Using a "ligate-Cross-Link-Purify" Strategy". . p. 2293 - 2301. Retrieved 2017.
• 2、 Bachmann, Michael,Brandt, Florian,Kopka, Klaus,Laube, Markus,Pietzsch, Jens,Ullrich, Martin,Wodtke, Robert,L?ser, Reik,Pietzsch, Hans-Jürgen,Van Den Hoff, J?rg. ""clickable" Albumin Binders for Modulating the Tumor Uptake of Targeted Radiopharmaceuticals". . p. 710 - 733. Retrieved 2022/01/11.
• 3、 Suto, Nanako,Kamoshita, Shione,Hosoya, Shoichi,Sakurai, Kaori. "Exploration of the Reactivity of Multivalent Electrophiles for Affinity Labeling: Sulfonyl Fluoride as a Highly Efficient and Selective Label". supporting information. p. 17080 - 17087. Retrieved 2021/07/02.