2,5-dioxopyrrolidin-1-yl 4-azidobenzoate

• ChemBase ID: 131778
• Molecular Formular: C11H8N4O4
• Molecular Mass: 260.20562
• Monoisotopic Mass: 260.05455476
• SMILES: c1cc(ccc1C(=O)ON1C(=O)CCC1=O)N=[N+]=[N-]
• Canonical SMILES: O=C(c1ccc(cc1)N=[N+]=[N-])ON1C(=O)CCC1=O
• InChI: InChI=1S/C11H8N4O4/c12-14-13-8-3-1-7(2-4-8)11(18)19-15-9(16)5-6-10(15)17/h1-4H,5-6H2
• InChIKey: LWAVGNJLLQSNNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 4-azidobenzoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 4-azidobenzoate
• Synonyms: 4-Azidobenzoic acid N-hydroxysuccinimide ester; N-羟基琥珀酰亚胺基 4-叠氮苯甲酸酯; 4-叠氮苯甲酸 N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 53053-08-0
• MDL Number: MFCD00054963
• PubChem SID: 162226055
• PubChem CID: 122153

CALCULATED PROPERTIES

• Acid pKa: 17.6973
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.5067381
• LogD (pH = 7.4): 1.5067381
• Log P: 1.6207837
• Molar Refractivity: 64.1556 cm^3
• Polarizability: 23.245113 Å^3
• Polar Surface Area: 93.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble50 mg/mL; DMF: soluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A9048

Application
光敏双异官能化交联剂。通常，初始反应通过在 6.5-8.5 的 pH 范围内形成酰胺键将酯偶联到伯胺。然后在紫外光 (250nm) 照射的过程中通过反应性氮烯发生二次键合。后一步的键合快速并且具有非特异性。
Other Notes
还原剂（如硫醇）可将叠氮化物还原为胺类，所以应当避免还原剂出现在反应中。初始操作和偶联反应应当在弱光照条件下进行。