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Tetrabutylammonium tribromide

Catalog Number
ACM38932808
Product Name
Tetrabutylammonium tribromide
Structure
Tetrabutylammonium tribromide
CAS
38932-80-8
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Synonyms
Mono(tetrabutylammonium) tribromide
Molecular Weight
482.18
Molecular Formula
C16H36Br3N
Canonical SMILES
CCCC[N+](CCCC)(CCCC)CCCC.Br[Br-]Br
InChI
InChI=1S/C16H36N.Br3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
InChI Key
XXSLZJZUSYNITM-UHFFFAOYSA-N
Melting Point
71-76 °C
Purity
99%
Solubility
Slightly soluble in acetone and chloroform
Appearance
Orange red solid
Storage
Keep in dark place, Inert atmosphere, Room Temperature
Complexity
116
Covalently-Bonded Unit Count
2
Exact Mass
481.03774
H-Bond Acceptor
1
Heavy Atom Count
20
MDL Number
MFCD00012110
Monoisotopic Mass
479.03979
Refractive Index
1.65
Rotatable Bond Count
12
Topological Polar Surface Area
0 Ų
Application
Tetrabutylammonium tribromide (TBATB) is a salt of the lipophilic tetrabutylammonium cation and the linear tribromide anion. It is used as a phase transfer catalyst in organic synthesis as well as a mild brominating agent. A wide range of O-isopropylidene derivatives can be prepared from the sugars and their derivatives on reaction with acetone at room temperature by employing 2 mol % of tetrabutylammonium tribromide as a catalyst. Good yields, low catalyst loading, mild reaction conditions, and a non-aqueous workup procedure are some major advantages of this protocol.

Tetrabutylammonium tribromide as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds.



It is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.

Tetra-n-butylammonium tribromide is useful for the preparation of vicinal dibromides from alkenes and alkynes and alfa-bromo acetals.

it is utilized to generate hydrogen bromide, which is used as an efficient chemoselective reagent for acetalization of carbonyl compounds.
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