771139
(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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
reaction suitability
reaction type: click chemistry, reagent type: cross-linking reagent
mp
350-355 °C
storage temp.
2-8°C
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+;
SMILES string
NCCNC(C1=CC=C(C=C1)/N=N/C2=CC=C(OCCCN=[N+]=[N-])C=C2)=O.[H]Cl
InChI key
UWCLSDSCVCQZQA-XMXXDQCKSA-N
form
solid
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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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
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)
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