2,5-dioxopyrrolidin-1-yl 5-azido-2-nitrobenzoate

• ChemBase ID: 155221
• Molecular Formular: C11H7N5O6
• Molecular Mass: 305.20318
• Monoisotopic Mass: 305.03963297
• SMILES: c1cc(c(cc1N=[N+]=[N-])C(=O)ON1C(=O)CCC1=O)[N+](=O)[O-]
• Canonical SMILES: O=C(c1cc(ccc1[N+](=O)[O-])N=[N+]=[N-])ON1C(=O)CCC1=O
• InChI: 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
• InChIKey: FUOJEDZPVVDXHI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 5-azido-2-nitrobenzoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 5-azido-2-nitrobenzoate
• Synonyms: N-(5-Azido-2-nitrobenzoyloxy)succinimide; N-Succinimidyl 5-azido-2-nitrobenzoate; 5-Azido-2-nitrobenzoic acid N-hydroxysuccinimide ester

Database IDs

• CAS Number: 60117-35-3
• MDL Number: MFCD00054962
• Beilstein Number: 1555224
• PubChem SID: 162249359
• PubChem CID: 3080866

CALCULATED PROPERTIES

• Acid pKa: 17.696785
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.4467223
• LogD (pH = 7.4): 1.4467223
• Log P: 1.5607679
• Molar Refractivity: 71.4803 cm^3
• Polarizability: 25.327133 Å^3
• Polar Surface Area: 138.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; ethyl acetate: soluble25 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C11H7N5O6

DETAILS

Sigma Aldrich - A3282

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

Sigma Aldrich - 11549

Other Notes
Photoactive, heterobifunctional cross-linker1