benzyl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase ID: 149952
• Molecular Formular: C12H11NO5
• Molecular Mass: 249.21944
• Monoisotopic Mass: 249.06372246
• SMILES: c1ccc(cc1)COC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCc1ccccc1
• 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
• InChIKey: MJSHDCCLFGOEIK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC Traditional name: benzyl 2,5-dioxopyrrolidin-1-yl carbonate
• Synonyms: Z-OSu; Benzyl N-succinimidyl carbonate; N-(Benzyloxycarbonyloxy)succinimide; N-(Benzyloxycarbonyloxy)succinimide; Cbz-ONSu; 苄基 N-琥珀酰亚胺基碳酸酯; N-(苄氧羰基氧基)琥珀酰亚胺; N-(苄氧基羰基氧基)丁二酰亚胺

Database IDs

• CAS Number: 13139-17-8
• EC Number: 236-075-3
• MDL Number: MFCD00005513
• Beilstein Number: 1387927
• PubChem SID: 24853653; 162244114
• PubChem CID: 83172

CALCULATED PROPERTIES

• Acid pKa: 17.634148
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.490004
• LogD (pH = 7.4): 1.490004
• Log P: 1.490004
• Molar Refractivity: 59.4337 cm^3
• Polarizability: 23.493593 Å^3
• Polar Surface Area: 72.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble0.1 g/mL, clear
• Melting Point: 77-82°C; 78-81 °C; 80-82 °C(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 98%; 99%
• Grade: purum
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C12H11NO5

DETAILS

Sigma Aldrich - 227781

Application
Reagent for the selective introduction of the Z-amino protection in amino acids1,2,3; and in aminoglycoside antibiotics4,5,6.
Packaging
25, 100, 250 g in poly bottle

Sigma Aldrich - 13631

Application
Reagent for the selective introduction of the Z-amino protection in amino acids1,2,3; and in aminoglycoside antibiotics4,5,6.

REFERENCES

• Selective reagent for the introduction of the benzyloxycarbonyl (Cbz or Z) protecting group, avoiding the formation of amino acid dimers: Tetrahedron Lett., 4765 (1966); J. Antibiot., 25, 695 (1972); 34, 513 (1981); Can. J. Chem., 60, 976 (1982).
• Especially convenient for the selective protection of the -amino group of lysine and ornithine: Can. J. Chem., 54, 733 (1976); Rec. Trav. Chim.,99, 400 (1980). See Appendix 6.