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A3282

Sigma-Aldrich

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

≥95%, powder

Synonym(s):

N-(5-Azido-2-nitrobenzoyloxy)succinimide, N-Succinimidyl 5-azido-2-nitrobenzoate

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About This Item

Empirical Formula (Hill Notation):
C11H7N5O6
CAS Number:
60117-35-3
Molecular Weight:
305.20
Beilstein:
1555224
MDL number:
MFCD00054962
UNSPSC Code:
12352106
PubChem Substance ID:
329770717

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S P Sheikh et al.
The Journal of biological chemistry, 265(14), 8304-8310 (1990-05-15)
Pharmacological studies indicate that peptide YY (PYY) and neuropeptide Y interact with multiple binding sites, categorized as Y1 and Y2 subtypes. In order to identify and structurally characterize the Y1 and Y2 receptors we covalently cross-linked [125I-Tyr36]PYY to its receptors.
O W Nadeau et al.
Biochemistry, 38(8), 2551-2559 (1999-02-25)
Phosphorylase kinase, a regulatory enzyme of glycogenolysis in skeletal muscle, is a hexadecameric oligomer consisting of four copies each of a catalytic subunit (gamma) and three regulatory subunits (alpha, beta, and delta, the last being endogenous calmodulin). The enzyme is
P Wang et al.
Journal of immunology (Baltimore, Md. : 1950), 157(1), 213-220 (1996-07-01)
Cytotoxic T lymphocytes recognize antigenic peptides presented by MHC class I molecules. The peptides are generated in the cytosol by proteasomes, and probably also other proteases, and are then translocated into the endoplasmic reticulum (ER) lumen. The transporters associated with
S A McMahan et al.
Biochemistry, 33(40), 12092-12099 (1994-10-11)
In an effort to better understand protein-protein photoaffinity cross-linking using aryl azides, we have tested a number of factors influencing the cross-linking of the sigma 70 subunit of Escherichia coli RNA polymerase to core RNA polymerase. These factors include the
M Nagao et al.
Nihon Naibunpi Gakkai zasshi, 66(10), 1108-1116 (1990-10-20)
We characterized structurally the receptors for somatostatin in rat cerebral cortex by affinity labeling with [125I-Tyr1] somatostatin. [125I-Tyr1] somatostatin was cross-linked to cerebrocortical membranes using photoreactive cross-linker: N-5-azido-2-nitrobenzoyloxy-succinimide. Analysis by autoradiography revealed a broad band centered at Mr = 72,000
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