Skip to Content
Merck
All Photos(1)

Documents

900919

Sigma-Aldrich

Azidoacetic acid NHS ester

Synonym(s):

(2,5-Dioxopyrrolidin-1-yl) 2-azidoacetate, 1-[(Azidoacetyl)oxy]pyrrolidine-2,5-dione

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C6H6N4O4
CAS Number:
824426-32-6
Molecular Weight:
198.14
MDL number:
MFCD24452499
UNSPSC Code:
12352106
NACRES:
NA.22

form

powder or crystals

Quality Level

100

reaction suitability

reagent type: cross-linking reagent

availability

available only in USA

storage temp.

−20°C

InChI

1S/C6H6N4O4/c7-9-8-3-6(13)14-10-4(11)1-2-5(10)12/h1-3H2

InChI key

FENNDBOWHRZLTQ-UHFFFAOYSA-N

Application

Azidoacetic acid NHS ester is a simple azido-containing reagent with an N-hydroxysuccinimide (NHS) ester that can be reacted with primary amines at pH 7-9 forming a stable amide bond. The azide allows for chemoselective ligation with an alkyne or cyclooctyne. It is generally used to functionalize amines and amino acids with azidoacetyl groups. It is generally used in click chemistry applications.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H242

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Click and Pick: Identification of Sialoside Analogues for Siglec?Based Cell Targeting.
Rillahan C D, et al.
Angewandte Chemie (International Edition in English), 51(44), 11014-11018 (2012)
Synthetic glycosphingolipids for live-cell labeling.
Dauner M, et al.
Bioconjugate Chemistry, 27(7), 1624-1637 (2016)
In vivo targeting of hydrogen peroxide by activatable cell-penetrating peptides.
Weinstain R, et al.
Journal of the American Chemical Society, 136(3), 874-877 (2014)
Tension sensing nanoparticles for mechano-imaging at the living/nonliving interface.
Liu Y, et al.
Journal of the American Chemical Society, 135(14), 5320-5323 (2013)
Nanoparticle tension probes patterned at the nanoscale: impact of integrin clustering on force transmission.
Liu Y, et al.
Nano Letters, 14(10), 5539-5546 (2014)

Articles

Crosslinkers Selection Guide

Choosing the right crosslinker for your biochemical or bioconjugation research can be challenging. Our selection guide can help you find the perfect match for your applications.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service