2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate

• ChemBase ID: 78372
• Molecular Formular: C19H15NO5
• Molecular Mass: 337.3261
• Monoisotopic Mass: 337.09502259
• SMILES: N1(C(=O)CCC1=O)OC(=O)OCC1c2c(cccc2)c2c1cccc2
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCC1c2ccccc2c2c1cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate; 2,5-dioxopyrrolidin-1-yl (9H-fluoren-9-yl)methyl carbonate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate
• Synonyms: Fmoc N-hydroxysuccinimide ester; Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl 9H-Fluoren-9-ylmethyl Ester; 1-[[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy]-2,5-pyrrolidinedione; (Fluorenylmethoxycarbonyl)hydroxysuccinimide Ester; Succinimidyl (9-Fluorenyl)methyl Carbonate; N-(9H-Fluoren-9-ylmethoxycarbonyloxy)succinimide; Fmoc N-Hydroxysuccinimide Ester; N-(9-Fluorenylmethoxycarbonyloxy)succinimide; (2,5-dioxopyrrolidin-1-yl) (9H-fluoren-9-ylmethyl) carbonate; (9H-Fluoren-9-yl)methyl N-succinimidyl carbonate; FMOC-ONSu; 1-{[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione; Fmoc-OSu; 9-Fluorenylmethyl N-succinimidyl carbonate; N-(9-Fluorenylmethoxycarbonyloxy)succinimide; Fmoc N-hydroxysuccinimide ester; Fmoc-OSu; 9-Fluorenylmethyl Succinimidyl Carbonate; FMOC-OSu; N-(9-Fluorenylmethoxycarbonyloxy)succinimide; 9-芴甲基 N-琥珀酰亚胺基碳酸酯; 9-芴甲基 N-琥珀酰亚氨基碳酸酯; 9-芴甲基 N-琥珀酰亚胺基碳酸酯; N-(9-芴甲氧羰基氧基)琥珀酰亚胺; N-(9-芴基甲氧基羰基)琥珀酰胺

Database IDs

• CAS Number: 82911-69-1
• EC Number: 433-520-5
• MDL Number: MFCD00010733
• Beilstein Number: 3569540
• PubChem SID: 24857201; 162043141; 24870572
• PubChem CID: 134122

CALCULATED PROPERTIES

• Acid pKa: 17.008211
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.9514215
• LogD (pH = 7.4): 2.9514215
• Log P: 2.9514215
• Molar Refractivity: 87.8335 cm^3
• Polarizability: 35.36318 Å^3
• Polar Surface Area: 72.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 147-153°C; 150 - 153°C; 150-153 °C(lit.); 150-153°C; 150-153°C
• Hydrophobicity(logP): 2.358

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Harmful/Irritant/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: UN3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: III
• Risk Statements: 22-43-51/53
• Safety Statements: 24-37-61
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H317-H411-H401; H302-H317-H411
• GHS Precautionary statements: P261-P301+P310-P302+P352-P321-P405-P501A; P273-P280
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >98%; ≥98.0% (HPLC); 95%; 96%; 98%
• Empirical Formula (Hill Notation): C19H15NO5

DETAILS

MP Biomedicals - 02199308

White to off-white crystalline powder, purity: ~ 98%
Reagent for the efficient synthesis of FMOC-amino acid, employed as building units in solid phase peptide synthesis.

Sigma Aldrich - 46920

Application
Most efficient reagent for the selective preparation of N-(9-fluorenylmethoxycarbonyl) derivatives of hydroxy-amino acids in high yield. Dipeptide formation is lower than with the chloroformate, Fmoc-Cl. It has been employed in the synthesis of glycopeptides.
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 289507

Application
Most efficient reagent for the selective preparation of N-(9-fluorenylmethoxycarbonyl) derivatives of hydroxy-amino acids in high yield. Dipeptide formation is lower than with the chloroformate, Fmoc-Cl. It has been employed in the synthesis of glycopeptides.
Packaging
5 g in glass bottle

Toronto Research Chemicals - F634000

Used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.

REFERENCES

• Heidenreich, O., et al.: J. Biol. Chem., 269, 2131 (1994)
• Kothe, U., et al.: Anal. Biochem., 356, 148 (1994)
• Thakkar, A., et al.: Anal. Chem., 78, 5935 (1994)
• Reagent for the preparation of Fmoc derivatives of amino acids, avoiding problems arising from mixed anhydride formation; preferred especially for the protection of hydroxy amino acids: Can. J. Chem., 60, 976 (1982); Biopolymers, 22, 2157 (1983); Synthesis, 671 (1978). For peptide reagents, see Appendix 6.