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301590

Sigma-Aldrich

Tetrabutylammonium tribromide

98%

Synonym(s):

TBABr3, Tetrabutylammonium bromide perbromide

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4NBr3
CAS Number:
38932-80-8
Molecular Weight:
482.18
Beilstein:
3746114
MDL number:
MFCD00012110
UNSPSC Code:
12352101
PubChem Substance ID:
24858199
NACRES:
NA.22

Assay

98%

mp

71-76 °C (lit.)

SMILES string

Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC

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

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Application

Tetrabutylammonium tribromide can be used:
  • As a catalyst in the preparation of O-isopropylidene derivatives of free sugars.
  • As a reagent in methanol for the cleavage of tert-butyldimethylsilyl (TBDMS) ethers chemoselectively.
  • As a catalyst in the synthesis of bis-indolymethanes by electrophilic substitution of indoles with different aldehydes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrabutylammonium tribromide (TBATB)- MeOH: An efficient chemoselective reagent for the cleavage of tert-butyldimethylsilyl (TBDMS) ethers
Gopinath R and Patel BK
Organic Letters, 2(26), 4177-4180 (2000)
Tetrabutylammonium tribromide (TBATB): a mild and efficient catalyst for O-isopropylidenation of carbohydrates
Khan AT, et al.
Carbohydrate Research, 346(5), 673-677 (2011)
Mild and Efficient Synthesis of bis-Indolylmethanes Catalyzed by Tetrabutylammonium Tribromide
Lin X, et al.
Synthetic Communications, 36(21), 3153-3160 (2006)
Shigeo Hayashi et al.
Journal of enzyme inhibition and medicinal chemistry, 29(6), 846-867 (2014-02-13)
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