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301590

Tetrabutylammonium tribromide

Name: Tetrabutylammonium tribromide
Brand: ALDRICH

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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): a mild and efficient catalyst for O-isopropylidenation of carbohydrates

Khan AT, et al.

Carbohydrate Research, 346(5), 673-677 (2011)

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)

Design, synthesis and structure-activity relationship studies of novel and diverse cyclooxygenase-2 inhibitors as anti-inflammatory drugs.

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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