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  • 771066 - tert-Butyl 2-(4-{[4-(3-azidopropoxy)phenyl]azo}benzamido)ethylcarbamate

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771066 Sigma-Aldrich

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

95%

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

  • CAS Number 1207289-71-1

  • Empirical Formula (Hill Notation) C23H29N7O4

  • Molecular Weight 467.52

  •  MDL number MFCD24849721

  •  PubChem Substance ID 329767469

  •  NACRES NA.22

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Properties

Related Categories Bifunctional Linkers, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper Click Chemistry,
Quality Level   100
assay   95%
mp   173-178 °C
storage temp.   2-8°C
SMILES string   CC(C)(C)OC(=O)NCCNC(=O)c1ccc(cc1)\N=N\c2ccc(OCCCN=[N+]=[N-])cc2
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

Description

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.

Packaging

25, 100 mg in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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