Phenyltrimethylammonium tribromide, 97%, Thermo Scientific Chemicals
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Phenyltrimethylammonium tribromide, 97%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Phenyltrimethylammonium tribromide, 97%, Thermo Scientific Chemicals

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Catalog number A15326.18
also known as A15326-18
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Chemical Identifiers
CAS4207-56-1
IUPAC NameN,N,N-trimethylanilinium; tribroman-2-uide
Molecular FormulaC9H14Br3N
InChI KeyPRXNKYBFWAWBNZ-UHFFFAOYSA-N
SMILESBr[Br-]Br.C[N+](C)(C)C1=CC=CC=C1
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SpecificationsSpecification SheetSpecification Sheet
FormCrystals or powder or crystalline powder
Melting Point (clear melt)110-118°C
Appearance (Color)Orange
Assay (Titration ex Bromide)≥96.0 to ≤104.0%
Phenyltrimethylammonium tribromide is used as brominating reagent for 1,2-addition of bromine to the double bond of α,β-unsaturated compounds.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Phenyltrimethylammonium tribromide is used as brominating reagent for 1,2-addition of bromine to the double bond of α,β-unsaturated compounds.

Solubility
Insoluble in water.

Notes
Hygroscopic. Incompatible with oxidizing agents, reducing agents and bases.
RUO – Research Use Only

General References:

  1. Lili Jin; Huanwang Jing; Tao Chang; Xiuli Bu; Li Wang; Zhongli Liu. Metal porphyrin/phenyltrimethylammonium tribromide: High efficient catalysts for coupling reaction of CO2 and epoxides. Journal of Molecular Catalysis A: Chemical. 2007, 261,(2), 262-266.
  2. T.Javed; S.S.Kahlon. Multi-step synthesis of benzopyranones via a key step involving reaction of the intermediate compound with phenyltrimethylammonium tribromide. Journal of Heterocyclic Chemistry. 2002, 39,(4), 627-630.
  3. 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).
  4. 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).
  5. Tosylhydrazones have been oxidized to N-alkenyl-N'-tosyldiazenes: J. Org. Chem., 39, 826 (1974).
  6. Catalyses the aziridination of alkenes by Chloramine-T trihydrate, A12044: J. Am. Chem. Soc., 120, 6844 (1998).