Benzyl succinimido carbonate
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Basic information
- CAS
13139-17-8- Standard SMILES
O=C(OCc1ccccc1)ON1C(=O)CCC1=O- InChIKey
MJSHDCCLFGOEIK-UHFFFAOYSA-N- Molecular formula
- C12H11NO5
- Average molar mass
- 249.22 g/mol
- Monoisotopic mass
- 249.06372245
Names & identifiers
- Preferred name
- Benzyl succinimido carbonate
- IUPAC
- benzyl (2,5-dioxopyrrolidin-1-yl) carbonate
- English name
- N-(Benzyloxycarbonyloxy)succinimide
- Molecular formula
- C12H11NO5
- Molecular weight
- 249.22
Names & synonyms
13139-17-8Benzyl succinimido carbonate2,5-Pyrrolidinedione, 1-[[(phenylmethoxy)carbonyl]oxy]-EINECS 236-075-3DTXSID201570202,5-Pyrrolidinedione, 1-(((phenylmethoxy)carbonyl)oxy)-RefChem:118901DTXCID9079511236-075-3N-(Benzyloxycarbonyloxy)succinimidebenzyl (2,5-dioxopyrrolidin-1-yl) carbonatecbz-osu
Show more names
Cbz-ClBENZYL N-SUCCINIMIDYL CARBONATEBENZYLOXYCARBONYLOXYSUCCINIMIDEZ-ONSUoxycarbonyL
Z-OSucbz-onsubenzyl 2,5-dioxopyrrolidin-1-yl carbonateMFCD00005513N-Carbobenzoxyoxysuccinimiden-(benzyloxycarbonyloxy) succinimideN-(N-Benzyloxycarbonyloxy)succinimideO-Cbz-N-hydroxysuccinimide
Database identifiers
- CAS
13139-17-8- PubChem CID
- 83172
- DTXSID
DTXSID20157020- EC Number
- 236-075-3
- Nikkaji
- J208.262D
Properties
Computed structural propertiesFilling in
- XLogP
- 1.1
- Topological polar surface area
- 72.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 332
Physicochemical properties
- Melting point
- 80 · 80-82 °C(lit.)
- Boiling point
- 392.32 °C · 392.32°C (rough estimate)
- Density
- 1.3189 · 1.3189 (rough estimate)
- refractive index
- 1.556 · 1.5560 (estimate)
- Flash point
- 81 °C · 81°C
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 0.1 g/mL, · acetone: 0.1 g/mL, clear
- form
- Fine Crystalline Powder
- color
- White to off-white
- Decomposition
- 81 · 81 ºC
- Sensitive
- Moisture Sensitive
- BRN
- 1387927 · 1387927
- Stability
- Stable. Moisture sensitive.
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 69.2% (9 of 13) of all reports.
Warning
H315 (23.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 13 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 28-02-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19071
2,5-Pyrrolidinedione, 1-(phenylmethoxy)carbonyloxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (23.1%)
Safety data
- F
- 8-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29252900
- risk_code
- 43-24/25-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesReagents for the selective introduction of the Z-protecting group into amino compounds
UsesN-(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.
Upstream & downstream products
Downstream products
Related reactions
342 records
Compound notes
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