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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

UNSPSC Code:

12352101

NACRES:

NA.22

PubChem Substance ID:

24858199

MDL number:

MFCD00012110

Beilstein/REAXYS Number:

3746114

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Properties

assay

98%

form

crystalline

reaction suitability

core: ammonium

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

Description

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

signalword

Warning

hcodes

H315,H319,H335

pcodes

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

11 - Combustible Solids

wgk

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): 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)

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