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82911-69-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:78372 http://www.chembase.cn/molecule-78372.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
82911-69-1
EC Number
433-520-5
MDL Number
MFCD00010733
Beilstein Number
3569540
PubChem SID
162043141
24857201
24870572
PubChem CID
134122

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 17.008211  H Acceptors
H Donor LogD (pH = 5.5) 2.9514215 
LogD (pH = 7.4) 2.9514215  Log P 2.9514215 
Molar Refractivity 87.8335 cm3 Polarizability 35.36318 Å3
Polar Surface Area 72.91 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
147-153°C expand Show data source
150 - 153°C expand Show data source
150-153 °C(lit.) expand Show data source
150-153°C expand Show data source
150-153°C expand Show data source
Hydrophobicity(logP)
2.358 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
Storage Warning
Harmful/Irritant/Moisture Sensitive/Store under Argon expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
X expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
UN3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
III expand Show data source
Risk Statements
22-43-51/53 expand Show data source
Safety Statements
24-37-61 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H301-H317-H411-H401 expand Show data source
H302-H317-H411 expand Show data source
GHS Precautionary statements
P261-P301+P310-P302+P352-P321-P405-P501A expand Show data source
P273-P280 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
>98% expand Show data source
≥98.0% (HPLC) expand Show data source
95% expand Show data source
96% expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C19H15NO5 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02199308 external link
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 external link
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 external link
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 external link
Used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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.
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PATENTS

PATENTS

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INTERNET

INTERNET

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