Tetra-n-butylammonium tribromide

• Catalog No.: 16258
• CAS Number: 38932-80-8
• M. F.: C16H36Br3N
• M. W.: 482.17574
• Purity: 98%

SYNONYMS

• Title: 四正丁基三溴化铵
• IUPAC name: tetrabutylazanium; tribroman-2-uide
• IUPAC Traditional name: tetrabutylammonium; tribroman-2-uide
• Synonyms: TBAB

DATABASE IDS

• Beilstein Number: 3746114
• CAS Number: 38932-80-8
• MDL Number: MFCD00012110

PROPERTIES

• Purity: 98%
• Apperance: Crystalline
• Melting Point: 74-76°C
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: III

REFERENCES

• Mild brominating agent. Alkenes are converted to vic-dibromides in high yields. In ethylene glycol, ketones can be converted directly to ɑ-bromo ethylene acetals in good yield, providing convenient access to ɑ,?-unsaturated ketones: Bull. Soc. Chim. Belg., 93, 157 (1984); Synth. Commun., 15, 213 (1985). Aromatic amines and phenols are selectively brominated in the p-position: Synth. Commun., 16, 1641 (1986); Can. J. Chem., 67, 2061 (1989); J. Chem. Res. (Synop.), 381 (1986); Tetrahedron Lett., 39, 8163 (1998).
• For Hofman rearrangemt of amides to ureas and carbamates, See: Bull. Chem. Soc. Jpn., 61, 1401 (1988).
• In catalytic amounts promotes dithioacetalization of aldehydes and ketones, and transthioacetalization of 1,3-dioxolanes and dioxanes with ethane- or propanedithiol: Org. Biomol. Chem., 2, 1670 (2004); the cleavage of dithioacetals to the corresponding carbonyl compounds with stoichiometric amounts of the reagent has also been described: Synlett, 785 (2001). Also catalyzes both the protection and deprotection of carbonyl compounds to 1,3-dithiolanes: Tetrahedron. Lett., 43, 2843 (2002), of aldehydes to 1,1-diacyloxy derivatives: Eur. J. Org. Chem., 441 (2005), and alcohols to tetrahydropyranyl (THP) ethers: Tetrahedron Lett., 42, 7679 (2001). In methanol, t-butyldimethylsilyl (TBDMS), THP, and 4,4'-dimethoxytrityl ethers undergo catalytic deprotection. The reaction is chemoselective, permitting, e.g. selective deprotection of primary DMT, TBDMS, and THP ethers in the presence of other ether protecting groups: Org. Lett., 2, 4177 (2000).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2681 (2006).