| Identification | More | [Name]
N-(Benzyloxycarbonyloxy)succinimide | [CAS]
13139-17-8 | [Synonyms]
2,5-PYRROLIDINEDIONE,1-[[(PHENYLMETHOXY)CARBONYL]OXY]-
BENZYL N-SUCCINIMIDYL CARBONATE
BENZYLOXYCARBONYL-N-HYDROXYSUCCINIMIDE
BENZYLOXYCARBONYLOXYSUCCINIMIDE
BENZYLOXYCARBONYLSUCCINIMIDE
BENZYLOXYLCARBONYLOXYSUCCINIMIDE
benzyl succinimido carbonate
(CARBOBENZOXY)SUCCINIMIDE
CARBONIC ACID BENZYL ESTER 2,5-DIOXO-PYRROLIDIN-1-YL ESTER
CBZ-ONSU
CBZ-OSU
LABOTEST-BB LT00053446
N-ALPHA-(BENZYLOXYCARBONYLOXY)SUCCINIMIDE
N-(BENZOYLOXYCARBONYLOXY)SUCCINIMIDE
N-BENZYLOXYCARBONYLOXYSUCCINAMIDE
N-(BENZYLOXYCARBONYLOXY)SUCCINIMIDE
N-(BENZYLOXYCARBONYL)-SUCCINIMIDE
N-CARBOBENZOXYOXYSUCCINIMIDE
N-CARBOBENZOXY-SUCCINIMIDE
O-CBZ-N-HYDROXYSUCCINIMIDE | [EINECS(EC#)]
236-075-3 | [Molecular Formula]
C12H11NO5 | [MDL Number]
MFCD00005513 | [Molecular Weight]
249.22 | [MOL File]
13139-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystal powde | [Melting point ]
80-82 °C(lit.)
| [Boiling point ]
392.32°C (rough estimate) | [density ]
1.3189 (rough estimate) | [refractive index ]
1.5560 (estimate) | [Fp ]
81°C | [storage temp. ]
2-8°C
| [solubility ]
acetone: 0.1 g/mL, clear
| [form ]
Fine Crystalline Powder | [color ]
White to off-white | [Stability:]
Stable. Moisture sensitive. | [Decomposition ]
81 ºC | [Sensitive ]
Moisture Sensitive | [Detection Methods]
HPLC,NMR | [BRN ]
1387927 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2 | [InChIKey]
MJSHDCCLFGOEIK-UHFFFAOYSA-N | [SMILES]
C(OCC1=CC=CC=C1)(=O)ON1C(=O)CCC1=O | [CAS DataBase Reference]
13139-17-8(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive;Light sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R43:May cause sensitization by skin contact.
R24/25:Toxic in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
8-10 | [HS Code ]
29280000 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white crystal powde | [Application]
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. | [Uses]
Reagents for the selective introduction of the Z-protecting group into amino compounds | [Synthesis]
A method for synthesizing N- (benzyloxycarbonyl) succinimide comprises the following steps of adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid alkali under stirring, after dropwise adding, adding succinic anhydride in batches, dehydrating at high temperature and in vacuum under acid catalysis until no water is extracted, preparing N-hydroxysuccinimide solution, adding alkali into the N-hydroxysuccinimide solution, adjusting the pH of the reaction solution, controlling the temperature to be 0 ~ 60 ℃, dropwise adding benzyl chloroformate, separating out an organic layer after dropwise adding, concentrating to be dry, and recrystallizing to obtain an N- (benzyloxycarbonyl) succinimide finished product.[1]
 | [References]
[1] Method for synthesizing N- (benzyloxycarbonyl) succinimide by one-pot two-phase method. Patent No. CN110698381A |
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