dibromane tris(pyrrolidin-2-one) hydrobromide

• ChemBase ID: 301839
• Molecular Formular: C12H22Br3N3O3
• Molecular Mass: 496.03338
• Monoisotopic Mass: 492.92112758
• SMILES: C1CC(=O)NC1.C1CC(=O)NC1.C1CC(=O)NC1.Br.BrBr
• Canonical SMILES: O=C1CCCN1.O=C1CCCN1.O=C1CCCN1.BrBr.Br
• InChI: InChI=1S/3C4H7NO.Br2.BrH/c3*6-4-2-1-3-5-4;1-2;/h3*1-3H2,(H,5,6);;1H
• InChIKey: KEWCNOMRTUONNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dibromane tris(pyrrolidin-2-one) hydrobromide
• IUPAC Traditional name: Brom tris(pyrrolidone) hydrobromide
• Synonyms: PHT; Pyrrolidone hydrotribromide; 2-Pyrrolidinone hydrotribromide; 2-吡咯烷酮 氢三溴化物

Database IDs

• CAS Number: 22580-55-8
• EC Number: 245-100-7
• MDL Number: MFCD00082241

CALCULATED PROPERTIES

• Acid pKa: 14.745904
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.57960933
• LogD (pH = 7.4): -0.57960933
• Log P: -0.5796093
• Molar Refractivity: 22.2579 cm^3
• Polarizability: 8.598534 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 88-90°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 97%

REFERENCES

• See also (2-Carboxyethyl)triphenylphosphonium tribromide, L00553, for alternative reagent.
• Mild, highly selective brominating agent. Ketones can be ɑ-brominated in the presence of a double bond: the low concentration of enol form consumes the bromine as it is slowly liberated: Can. J. Chem., 47, 706 (1969). Acid sensitive substrates can be brominated with PHT with excess pyrrolidinone: Synthesis, 59 (1990). Bromination with PHT is facilitated by the presence of free radicals or trace peroxides (as in THF or dioxane). In DMSO, dehydrobromination may occur: J. Org. Chem., 55, 6161 (1990):