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N-(Benzyloxycarbonyloxy)succinimide

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N-(Benzyloxycarbonyloxy)succinimide Basic information

Product Name:
N-(Benzyloxycarbonyloxy)succinimide
Synonyms:
  • BENZYLOXYCARBONYL-N-HYDROXYSUCCINIMIDE
  • BENZYLOXYLCARBONYLOXYSUCCINIMIDE
  • BENZYLOXYCARBONYLSUCCINIMIDE
  • BENZYLOXYCARBONYLOXYSUCCINIMIDE
  • BENZYL N-SUCCINIMIDYL CARBONATE
  • benzyl succinimido carbonate
  • CBZ-ONSU
  • CBZ-OSU
CAS:
13139-17-8
MF:
C12H11NO5
MW:
249.22
EINECS:
236-075-3
Product Categories:
  • Medical Intermediates
  • Peptide coupling agents
  • Amino Acid Derivatives
  • Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
  • N-Protecting Reagents
  • Biochemistry
  • Condensation & Active Esterification
  • N-Substituted Maleimides, Succinimides & Phthalimides
  • N-Substituted Succinimides
  • Peptide Synthesis
  • Protective Reagents (Peptide Synthesis)
  • Synthetic Organic Chemistry
  • Cbz-Amino acid series
Mol File:
13139-17-8.mol
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N-(Benzyloxycarbonyloxy)succinimide Chemical Properties

Melting point:
80-82 °C(lit.)
Boiling point:
392.32°C (rough estimate)
Density 
1.3189 (rough estimate)
refractive index 
1.5560 (estimate)
Flash point:
81°C
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
acetone: 0.1 g/mL, clear
form 
Fine Crystalline Powder
color 
White to off-white
Decomposition 
81 ºC
Sensitive 
Moisture Sensitive
BRN 
1387927
Stability:
Stable. Moisture sensitive.
CAS DataBase Reference
13139-17-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
43-24/25-36/37/38-20/21/22
Safety Statements 
22-24/25-36-26
WGK Germany 
3
8-10
HS Code 
29252900

MSDS

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N-(Benzyloxycarbonyloxy)succinimide Usage And Synthesis

Chemical Properties

white crystal powde

Uses

Reagents for the selective introduction of the Z-protecting group into amino compounds

Uses

N-(N-Benzyloxycarbonyloxy)succinimide is a reagent used in the preparation of peptide thioacids view peptide precursors. Also used in the preparation of amino glycoside derivatives for the function of topoisomerase for both human and bacterial inhibition.

Uses

N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines. This reaction is one of the key synthetic steps in the synthesis of:

  • Enantiomers of cyclic methionine analogs viz, (R)-and (S)-3-aminotetrahydrothiophene- 3-carboxylic acid.
  • 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.
  • Total synthesis of (-)-diazonamide A. and (-)-sanglifehrin A.

Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis. It can also be used in N-trans diprotection of cyclen regioselectively.

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