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301590

Sigma-Aldrich

Tetrabutylammonium tribromide

98%

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Synonym(s):
TBABr3, Tetrabutylammonium bromide perbromide
Linear Formula:
(CH3CH2CH2CH2)4NBr3
CAS Number:
Molecular Weight:
482.18
Beilstein/REAXYS Number:
3746114
MDL number:
PubChem Substance ID:
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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This Item
323314133248376426
vibrant-m

301590

Tetrabutylammonium tribromide

vibrant-m

323314

Tetrabutylammonium thiocyanate

vibrant-m

133248

Pyridinium tribromide

vibrant-m

376426

Benzyltrimethylammonium tribromide

assay

98%

assay

98%

assay

90%

assay

97%

mp

71-76 °C (lit.)

mp

120-123 °C (lit.)

mp

-

mp

99-101 °C (lit.)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
Mild and Efficient Synthesis of bis-Indolylmethanes Catalyzed by Tetrabutylammonium Tribromide
Lin X, et al.
Synthetic Communications, 36(21), 3153-3160 (2006)
Tetrabutylammonium tribromide (TBATB): a mild and efficient catalyst for O-isopropylidenation of carbohydrates
Khan AT, et al.
Carbohydrate Research, 346(5), 673-677 (2011)
Shigeo Hayashi et al.
Journal of enzyme inhibition and medicinal chemistry, 29(6), 846-867 (2014-02-13)
Because of the pivotal role of cyclooxygenase (COX) in the inflammatory processes, non-steroidal anti-inflammatory drugs (NSAIDs) that suppress COX activities have been used clinically for the treatment of inflammatory diseases/syndromes; however, traditional NSAIDs exhibit serious side-effects such as gastrointestinal damage

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