N-(9-Fluorenylmethoxycarbonyloxy)succinimide

HCID 134122CAS 82911-69-1

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Grundinformationen

Standard-SMILES: O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O
InChIKey: WMSUFWLPZLCIHP-UHFFFAOYSA-N
Summenformel: C19H15NO5
Durchschnittliche Molmasse: 337,3 g/mol
Monoisotopische Masse: 337,09502258

Überblick

used in the preparation of Fmoc-amino acids

Namen und Bezeichner

Bevorzugter Name: N-(9-Fluorenylmethoxycarbonyloxy)succinimide
IUPAC: (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate
Englischer Name: Fmoc-OSu
Summenformel: C19H15NO5
Molmasse: 337.33

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

CAS: 82911-69-1
PubChem CID: 134122
DTXSID: DTXSID90232090
UNII: AD7AUS3GKT
EC Number: 433-520-5、617-400-1
Nikkaji: J208.522D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 72,9 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 5
Schwere Atome: 25
Formalladung: 0
Komplexität: 524

Physikochemische Eigenschaften

Schmelzpunkt: 150 · 150-153 °C(lit.)
Siedepunkt: 150 · 150-153°C
Dichte: 1.346 · 1.3460 (rough estimate)
Brechungsindex: 1.5 · 1.5000 (estimate)
storage temp.: 2 · 2-8°C
Löslichkeit: Soluble in dimethyl sulfoxide and dimethyl formamide.
Aggregatzustand: Microfine Powder
Farbe: White or almost white
BRN: 3569540 · 3569540
Stabilität: 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
CAS Datenbank: 82911 · 82911-69-1(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 · 4 Einträge

Acute Tox. 4 (100%)

Acute Tox. 4 (98.8%)

Acute toxicity - category 4

Acute Tox. 4 *

Sicherheitsdaten

F: 10-21
wgk: 3
ridadr: UN 3077 9 / PGIII
hs_code: 29251995
risk_code: 36/37/38-51/53-43-22
hazard_code: Xi,N,Xn
hazard_note: Moisture Sensitive
safety_code: 22-24/25-26/37/39-26-61-37-24
hazard_class: 9
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Skin Sens. 1

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungFmoc-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.

VerwendenN-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.