Basic information
- CAS
82911-69-1- Standard SMILES
O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O- InChIKey
WMSUFWLPZLCIHP-UHFFFAOYSA-N- Molecular formula
- C19H15NO5
- Average molar mass
- 337.3 g/mol
- Monoisotopic mass
- 337.09502258
Overview
used in the preparation of Fmoc-amino acids
Names & identifiers
- Preferred name
- N-(9-Fluorenylmethoxycarbonyloxy)succinimide
- IUPAC
- (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate
- English name
- Fmoc-OSu
- Molecular formula
- C19H15NO5
- Molecular weight
- 337.33
Names & synonyms
82911-69-1N-(9-Fluorenylmethoxycarbonyloxy)succinimideFmoc-onsu9-Fluorenylmethylsuccinimidyl carbonateAD7AUS3GKTDTXSID902320902,5-PYRROLIDINEDIONE, 1-[[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]OXY]-2,5-Pyrrolidinedione, 1-(((9H-fluoren-9-ylmethoxy)carbonyl)oxy)-RefChem:926928DTXCID90154581433-520-5Fmoc-OSu
Show more names
Fomc-OsuFMOC-SU2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylMethyl carbonateFMOC-Succinimide
Fmoc N-hydroxysuccinimide ester9-Fluorenylmethyl succinimidyl carbonate(9H-fluoren-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate(2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate9-Fluorenylmethyl N-succinimidyl carbonateN-(9-Fluorenylmethoxycarbonyloxy) succinimideMFCD00010733C19H15NO5
Database identifiers
- CAS
82911-69-1- PubChem CID
- 134122
- DTXSID
DTXSID90232090
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 72.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 524
Physicochemical properties
- Melting point
- 150 · 150-153 °C(lit.)
- Boiling point
- 150 · 150-153°C
- Density
- 1.346 · 1.3460 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in dimethyl sulfoxide and dimethyl formamide.
- form
- Microfine Powder
- color
- White or almost white
- Sensitive
- Moisture Sensitive
- BRN
- 3569540 · 3569540
- Stability
- Moisture Sensitive
- Major Application
- peptide synthesis
- InChI
- InChI=1S/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2
- InChIKey
- WMSUFWLPZLCIHP-UHFFFAOYSA-N
- SMILES
- C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)(=O)ON1C(=O)CCC1=O
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
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H302 (98.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Status: Active Update: 29-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13924
2,5-Pyrrolidinedione, 1-(9H-fluoren-9-ylmethoxy)carbonyloxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute Tox. 4 (98.8%)
Acute toxicity - category 4
Acute Tox. 4 *
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29251995
- risk_code
- 36/37/38-51/53-43-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi,N,Xn
- hazard_note
Chemistry & industry
Applications
DescriptionFmoc-OSu (N-(9-Fluorenylmethoxycarbonyloxy)succinimide) is a reagent used in solid-phase peptide synthesis (SPPS) for Fmoc protection of amino groups, particularly amino acids. This reagent contains an Fmoc functional group, which is stable under acidic conditions and cleaves under alkaline conditions. Fmoc-OSu reacts with amino groups to form stable amide bonds, helping to reduce the occurrence of side reactions. Additionally, Fmoc-OSu can also be used as a fluorescent reagent.
UsesN-protecting reagent for oligonucleotide and peptide syntheses
UsesReagent for the preparation of pure Fmoc amino acids free from contamination by Fmoc-dipeptides.
UsesN-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.
Upstream & downstream products
Downstream products
Related reactions
162 records
Compound notes
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