Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

771066

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

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

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
form:
powder
Assay:
95%

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBP2298V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Disperse Red 1 Dye content 95 %

Sigma-Aldrich

344206

Disperse Red 1

4-Aminoazobenzene analytical standard

Supelco

46130

4-Aminoazobenzene

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)

Questions

Reviews

No rating value

Active Filters

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