(2-bromophenyl)methyl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase ID: 147899
• Molecular Formular: C12H10BrNO5
• Molecular Mass: 328.1155
• Monoisotopic Mass: 326.97423443
• SMILES: c1ccc(c(c1)COC(=O)ON1C(=O)CCC1=O)Br
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCc1ccccc1Br
• InChI: InChI=1S/C12H10BrNO5/c13-9-4-2-1-3-8(9)7-18-12(17)19-14-10(15)5-6-11(14)16/h1-4H,5-7H2
• InChIKey: SZDNRTVADOCWKU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-bromophenyl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC Traditional name: (2-bromophenyl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• Synonyms: Z(2-Br)-OSu; N-(2-Bromobenzyloxycarbonyloxy)succinimide; Z(2-Br)-OSu, N-(2-Bromobenzyloxycarbonyloxy)succinimide; 2-Bromobenzyl succinimidyl carbonate; 2-Bromobenzyl succinimdyl carbonate; N-(2-Bromobenzyloxycarbonyloxy)succinimide; N-(2-Bromobenzyloxycarbonyloxy)succinimide; N-(2-溴苄氧基羰基氧基)琥珀酰亚胺; Z(2-Br)-OSu，N-(2-溴苄氧羰酰氧基)丁二酰亚胺; 2-溴苄基-N-琥珀酰亚胺基碳酸酯; N-(2-溴苄氧羰氧基)丁二酰亚胺

Database IDs

• CAS Number: 128611-93-8
• MDL Number: MFCD00082848
• Beilstein Number: 3623239
• PubChem SID: 162242080
• PubChem CID: 598169

CALCULATED PROPERTIES

• Acid pKa: 17.634148
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.2587566
• LogD (pH = 7.4): 2.2587566
• Log P: 2.2587566
• Molar Refractivity: 67.0565 cm^3
• Polarizability: 26.482992 Å^3
• Polar Surface Area: 72.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 105-108°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: UN3335
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: III
• Risk Statements: 43
• Safety Statements: 24-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H317
• GHS Precautionary statements: P261-P280-P302+P352-P321-P363-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C12H10BrNO5

REFERENCES

• Reagent for introduction of the 2-bromobenzyloxycarbonyl group, recommended for protection of the phenol group of tyrosine residues in peptide synthesis. The group is cleaved quantitatively by HF: J. Org. Chem., 38, 591 (1973). See Appendix 6.