N,N,N-trimethylanilinium dibromane bromide

• ChemBase ID: 295355
• Molecular Formular: C9H14Br3N
• Molecular Mass: 375.92616
• Monoisotopic Mass: 372.86763545
• SMILES: C[N+](C)(C)c1ccccc1.[Br-].BrBr
• Canonical SMILES: C[N+](c1ccccc1)(C)C.BrBr.[Br-]
• InChI: InChI=1S/C9H14N.Br2.BrH/c1-10(2,3)9-7-5-4-6-8-9;1-2;/h4-8H,1-3H3;;1H/q+1;;/p-1
• InChIKey: COWLJVGUJFXIFR-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N,N-trimethylanilinium dibromane bromide
• IUPAC Traditional name: Brom tetrabutylammonium tribromide bromide
• Synonyms: N,N,N-Trimethylanilinium tribromide; Trimethylphenylammonium tribromide; Phenyltrimethylammonium tribromide; 苯基三甲基三溴化铵

Database IDs

• CAS Number: 4207-56-1
• EC Number: 224-127-8
• MDL Number: MFCD00011789
• Beilstein Number: 3919459
• PubChem SID: 180680886
• PubChem CID: 2723868

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -1.96705
• LogD (pH = 7.4): -1.96705
• Log P: -1.96705
• Molar Refractivity: 55.6793 cm^3
• Polarizability: 17.334887 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 112-117°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Corrosive (C)
• UN Number: UN3261
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310

Product Information

• Purity: 97%

REFERENCES

• Reagent for the selective ɑ-bromination of acetals with good stability and solubility in organic solvents such as THF: Tetrahedron Lett., 24 (1959); Bull. Soc. Chim. Fr., 1822 (1961); 90 (1962). For example of use in a one-pot ɑ-bromoacetalization of carbonyl compounds in high yields, see: Synthesis, 309 (1982).
• For example of selective ɑ-monobromination of ketones, see: Org. Synth. Coll., 6, 175 (1988). Silyl enol ethers are also ɑ-brominated with this reagent to give ɑ-bromo enones: Synlett, 651 (1994).
• Tosylhydrazones have been oxidized to N-alkenyl-N'-tosyldiazenes: J. Org. Chem., 39, 826 (1974).
• Catalyses the aziridination of alkenes by Chloramine-T trihydrate, A12044: J. Am. Chem. Soc., 120, 6844 (1998).