A3282

5-Azido-2-nitrobenzoic acid N-hydroxysuccinimide ester

≥95%, powder

• Synonym(s): N-(5-Azido-2-nitrobenzoyloxy)succinimide, N-Succinimidyl 5-azido-2-nitrobenzoate
• Empirical Formula (Hill Notation): C₁₁H₇N₅O₆
• CAS Number: 60117-35-3
• Molecular Weight: 305.20
• PubChem Substance ID: 329770717
• UNSPSC Code: 12352106
• Beilstein/REAXYS Number: 1555224
• MDL number: MFCD00054962
• Assay: ≥95%
• Form: powder

Properties

• assay: ≥95%
• form: powder
• reaction suitability: reagent type: cross-linking reagent
• color: yellow to yellow-orange
• solubility: ethyl acetate: 25 mg/mL, DMF: soluble
• functional group: NHS ester
• storage temp.: 2-8°C
• SMILES string: O=C(ON1C(CCC1=O)=O)C2=C(C=CC(N=[N+]=[N-])=C2)[N+]([O-])=O
• InChI: 1S/C11H7N5O6/c12-14-13-6-1-2-8(16(20)21)7(5-6)11(19)22-15-9(17)3-4-10(15)18/h1-2,5H,3-4H2
• InChI key: FUOJEDZPVVDXHI-UHFFFAOYSA-N

Description

Application

Photoactive, heterobifunctional cross-linking reagent. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. Second bonding occurs during UV irradiation (250-350 nm) via reactive nitrene. The latter bonding is rapid and non-specific.

Other Notes

Note that the nitro substituent provides an absorption band at a longer wavelength compared to simple aryl azide.

Disclaimer

Reducing agents such as thiols may reduce the azide to amine and should be avoided. Initial manipulations and coupling should be performed under reduced light.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)