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Sigma-Aldrich

tert-Butyl 2-(4-{[4-(3-azidopropoxy)phenyl]azo}benzamido)ethylcarbamate

95%

Synonym(s):

N-[2-(4-{2-[4-(3-Azidopropoxy)phenyl]diazenyl}benzoyl)amino]ethylcarbamic acid 1,1-dimethylethyl ester

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About This Item

Empirical Formula (Hill Notation):
C23H29N7O4
CAS Number:
1207289-71-1
Molecular Weight:
467.52
MDL number:
MFCD24849721
UNSPSC Code:
12352200
PubChem Substance ID:
329767469
NACRES:
NA.22

Assay

95%

form

powder

reaction suitability

reagent type: linker

mp

173-178 °C

functional group

Boc
amine
azide

storage temp.

2-8°C

SMILES string

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

InChI

1S/C23H29N7O4/c1-23(2,3)34-22(32)26-15-14-25-21(31)17-5-7-18(8-6-17)28-29-19-9-11-20(12-10-19)33-16-4-13-27-30-24/h5-12H,4,13-16H2,1-3H3,(H,25,31)(H,26,32)/b29-28+

InChI key

IEGYTTZAHJJGLG-ZQHSETAFSA-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. Boc group on the primary amine can be removed under acidic conditions (MeOH, CH3COCl, 0 degrees C to RT, Et2O, 1 h). The azide can be reacted with a terminal alkyne or cyclooctyne derivative via the 1,3 dipolar cycloaddition click chemistry reaction.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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