2,5-dioxopyrrolidin-1-yl 2-bromoacetate

• ChemBase ID: 155192
• Molecular Formular: C6H6BrNO4
• Molecular Mass: 236.02014
• Monoisotopic Mass: 234.94801968
• SMILES: C1CC(=O)N(C1=O)OC(=O)CBr
• Canonical SMILES: BrCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C6H6BrNO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2
• InChIKey: NKUZQMZWTZAPSN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 2-bromoacetate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 2-bromoacetate
• Synonyms: Bromoacetic acid N-hydroxysuccinimide ester; 2-Bromoacetic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; 1-[(Bromoacetyl)oxy]- 2,5-Pyrrolidinedione; Bromoacetic Acid N-Hydroxysuccinimide Ester; N-Hydroxysuccinimide Bromoacetate; N-Succinimidyl Bromoacetate; O-Bromoacetyl-N-hydroxysuccinimide; α-Bromoacetyl N-Hydroxysuccinimide; N-Succinimidyl Bromoacetate

Database IDs

• CAS Number: 42014-51-7
• MDL Number: MFCD00058571
• PubChem SID: 162249330; 24892067
• PubChem CID: 3565210

CALCULATED PROPERTIES

• Acid pKa: 17.706558
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.13092126
• LogD (pH = 7.4): -0.13092126
• Log P: -0.13092126
• Molar Refractivity: 40.9342 cm^3
• Polarizability: 16.3713 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble25 mg/mL; Chloroform; DMF: soluble
• Apperance: powder; White Solid
• Melting Point: 109-111°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ~95%
• Quality Level: PREMIUM
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C6H6BrNO4

DETAILS

Sigma Aldrich - B8271

Application
A heterobifunctional cross-linking reagent which allows bromoacetylation of primary amine groups followed by coupling to sulfhydryl-containing compounds. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. The second reaction results in thioether bonding in pH range 7.0-8.0.
Caution
The bromoacetyl group is light sensitive.

Toronto Research Chemicals - S690280

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent.

REFERENCES

• Cuatrecases, P., et al.: J. Biol. Chem., 244, 4316 (1969)
• Bernatowicz, M.S., et al.: Anal. Biochem., 155, 95 (1986)