[016258] CAS 38932-80-8 | Tetra-n-butylammonium tribromide, 98%

CAS : 38932-80-8
MDL : MFCD00012110

Other name :

TBAB

Chemical Properties

Formula : C16H36Br3N
Formula weight : 482.18
Melting Point : 74-76°
Sensitivity : Ambient temperatures.
Form : Crystalline
Solubility : Insoluble in water.

Literature 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,ß-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).

Notes

Incompatible with strong oxidizing agents.Other References:Beilstein: 3746114

Grade Specifications

Grade Specifications

Hazard Statements : H314-H318Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501aDo not breathe dust/fume/gas/mist/vapours/spray.IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.