771066

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
• 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

Properties

• 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

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable