2,5-dioxopyrrolidin-1-yl 2-chloroacetate

• ChemBase ID: 164085
• Molecular Formular: C6H6ClNO4
• Molecular Mass: 191.56914
• Monoisotopic Mass: 190.99853536
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCl
• Canonical SMILES: ClCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C6H6ClNO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2
• InChIKey: OWZGNRBFMASABS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 2-chloroacetate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 2-chloroacetate
• Synonyms: N-(Chloroacetoxy)succinimide; 2-Chloroacetic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; 2-Chloroacetic Acid N-Hydroxysuccinimide Ester; 1-[(Chloroacetyl)oxy]-2,5-pyrrolidinedione; N-Succinimidyl 2-chloroacetate

Database IDs

• CAS Number: 27243-15-8
• PubChem SID: 162258220
• PubChem CID: 12535337

CALCULATED PROPERTIES

• Acid pKa: 17.705503
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.3164165
• LogD (pH = 7.4): -0.3164165
• Log P: -0.3164165
• Molar Refractivity: 37.9507 cm^3
• Polarizability: 15.267298 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C363375

N-(chloroacetoxy)succinimide is a N-hydroxysuccinimide ester of a simple carboxylic acid. N-(chloroacetoxy)succinimide is used in the preparation of organometallic complexes and other synthetic probes for the labeling of proteins.

REFERENCES

• Salmain, M. et al.: Bioconj. Chem., 4, 425 (1993)
• Nonaka, H. et al.: J. AM. Chem. Soc., 129, 15777 (1993)