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MilliporeSigma

86870

Sigma-Aldrich

Cloruro de tetrabutilamonio

greener alternative

≥97.0% (NT)

Sinónimos:

N,N,N-tributyl-butanaminium chloride

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25 G
$100.00
100 G
$280.00
500 G
$1,010.00

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25 G
$100.00
100 G
$280.00
500 G
$1,010.00

About This Item

Fórmula lineal:
[CH3(CH2)3]4NCl
Número de CAS:
Peso molecular:
277.92
Beilstein/REAXYS Number:
3571227
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

$100.00


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Quality Level

assay

≥97.0% (NT)

form

crystals

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

impurities

≤1% water

solubility

H2O: 20 mg/mL, clear, colorless

greener alternative category

SMILES string

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

InChI

1S/C16H36N.ClH/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

NHGXDBSUJJNIRV-UHFFFAOYSA-M

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General description

Tetrabutylammonium chloride is a quaternary ammonium salt that is commonly used as a phase transfer catalyst as well as a source of chloride ions in organic synthesis.

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

Tetrabutylammonium chloride (TBACl) can be used as a phase transfer catalyst in the synthesis of:
  • 2-Amino-4H-chromene derivatives by the condensation reaction of aldehydes, malononitrile, and α, or β-naphthol.[1]
  • Methyl esters by esterification reaction of carboxylic acids with dimethyl carbonate in the presence of K2CO3.[2]
It has also been used as an initiator to synthesize 11-trifluoromethylated dibenzodiazepines via cascade radical addition/cyclization of o-isocyanodiaryl amines.[3]

TBACl can also be used with phosphorus pentoxide for greener deoxychlorination.

Process for Producing Halogenated Heteroaryl Compounds

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Nancy AlHaddad et al.
Organic & biomolecular chemistry, 17(31), 7330-7336 (2019-07-18)
The present study describes the synthesis of the first phenoxycalix[4]pyrrole-epichlorohydrin based polymer. The advantage of the latter resides in its fast-single step synthesis protocol, low cost, water insolubility and its unexpected anion extraction capacity. The study of this polymer by
Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines
Yuan S, et al.
The Journal of Organic Chemistry, 87, 16542-16549 (2022)
Efficient and eco-friendly synthesis of 2-amino-4H-chromene derivatives using catalytic amount of tetrabutylammonium chloride (TBAC) in water and solvent-free conditions
Mehrabi H and Kamali N
Journal of the Iranian Chemical Society, 9, 599-605 (2012)
I P E Macário et al.
Scientific reports, 9(1), 3932-3932 (2019-03-10)
The tailor-made character of deep eutectic solvents (DES) turns them very attractive to be used in several applications, including in health-related areas such as pharmaceutical, nutraceutical, and cosmetic industries. However, although DES has been touted as "green" solvents, several works
Methyl esterification of carboxylic acids with dimethyl carbonate promoted by K2CO3/tetrabutylammonium chloride
Chau K, et al.
Green Chemistry Letters and Reviews, 6, 89-93 (2013)

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. 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/449/386/product-dating-information-mk.pdf

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