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Merck
CN

771139

Sigma-Aldrich

(E)-N-(2-Aminoethyl)-4-{2-[4-(3-azidopropoxy)phenyl]diazenyl}benzamide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H21N7O2 · HCl
Molecular Weight:
403.87
MDL number:
MFCD25976530
UNSPSC Code:
12352200
PubChem Substance ID:
329767474
NACRES:
NA.22

Key Documents

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form

solid

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

mp

350-355 °C

storage temp.

2-8°C

SMILES string

NCCNC(C1=CC=C(C=C1)/N=N/C2=CC=C(OCCCN=[N+]=[N-])C=C2)=O.[H]Cl

InChI

1S/C18H21N7O2.ClH/c19-10-12-21-18(26)14-2-4-15(5-3-14)23-24-16-6-8-17(9-7-16)27-13-1-11-22-25-20;/h2-9H,1,10-13,19H2,(H,21,26);1H/b24-23+;

InChI key

UWCLSDSCVCQZQA-XMXXDQCKSA-N

Application

Azobenzene cleavable linker. Treatment with sodium dithionite (sodium hydrosulfite) reduces azo functionality, cleaving the N-N bond to yield two primary amines.
Has been used in proteomic and affinity chromatography applications. The free primary amine can be linked to any carboxylic acid containing compound or biomolecule via standard amide bond forming procedures.The azide can be reacted with a terminal alkyne or cyclooctyne derivative via the 1,3 dipolar cycloaddition click chemistry reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP2301V

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A mild chemically cleavable linker system for functional proteomic applications.
Steven H L Verhelst et al.
Angewandte Chemie (International ed. in English), 46(8), 1284-1286 (2007-01-06)
Felicetta Landi et al.
Organic & biomolecular chemistry, 8(1), 56-59 (2009-12-22)
A new chemically-cleavable linker has been synthesised for the affinity-independent elution of biomolecules by classical affinity chromatography. This azo-based linker is shown to couple efficiently with "click" derivatised ligands such as biotin propargyl amide through a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition

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