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140775

Tetrabutylammonium iodide

98%, reagent grade, solid

Synonym(s):

TBAI

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25 g

Available to ship TODAYfromMILWAUKEE

$34.80
100 g

Available to ship TODAYfromMILWAUKEE

$97.50
500 g

Available to ship TODAYfromMILWAUKEE

$241.00

About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
Molecular Weight:
369.37
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352107
EC Number:
206-220-5
MDL number:
Beilstein/REAXYS Number:
3916152

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Product Name

Tetrabutylammonium iodide, reagent grade, 98%

grade

reagent grade

assay

98%

form

solid

reaction suitability

core: ammonium

mp

141-143 °C (lit.)

SMILES string

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

InChI

1S/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1

InChI key

DPKBAXPHAYBPRL-UHFFFAOYSA-M

Application

Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
  • Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
  • Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
  • Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.


Other reactions where TBAI can be used as a catalyst:
  • TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
  • Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
  • Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.


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This Item
23594686903345857
assay

98%

assay

99%

assay

≥99.0% (AT)

assay

98%

reaction suitability

core: ammonium

reaction suitability

core: ammonium

reaction suitability

-

reaction suitability

core: ammonium

form

solid

form

solid

form

crystals

form

solid

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

mp

141-143 °C (lit.)

mp

>300 °C (lit.)

mp

141-143 °C (lit.), 144-148 °C

mp

41-44 °C (lit.)

grade

reagent grade

grade

-

grade

-

grade

-


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pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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New Efficient Nickel-and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide.
Piber M,et al.
Organic Letters, 9(1), 1323-1326 (1999)
Tetrabutylammonium iodide catalyzed allylic sulfonylation of α-methyl styrene derivatives with sulfonylhydrazides.
Li X Xu X and Zhou C
Chemical Communications (Cambridge, England), 48(100), 12240-12242 (2012)
Efficient carbamate synthesis via a three-component coupling of an amine, CO2, and alkyl halides in the presence of Cs2CO3 and tetrabutylammonium iodide.
Salvatore R N, et al.
The Journal of Organic Chemistry, 66(3), 1035-1037 (2001)



Global Trade Item Number

SKUGTIN
140775-100G04061838733672
140775-25G04061838733689
140775-500G04061838733696

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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