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Tetrabutylammonium hydroxide

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In this page talks about ( Tetrabutylammonium hydroxide ) It was sent to us on 05/03/2021 and was presented on 05/03/2021 and the last update on this page on 05/03/2021

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  {{chembox
verifiedrevid = 470603420
ImageFile=TBAH.PNG
ImageSize=
IUPACName=tetrabutylammonium hydroxide
OtherNames= TBAH, TBAOH
Section1={{Chembox Identifiers
ChemSpiderID_Ref =
ChemSpiderID = 2005872
InChI = 1/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1
InChIKey = VDZOOKBUILJEDG-REWHXWOFAE
StdInChI_Ref =
StdInChI = 1S/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1
StdInChIKey_Ref =
StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M
CASNo_Ref =
CASNo=2052-49-5
UNII_Ref =
UNII = 68I858J9S1
PubChem=2723671
ChEMBL_Ref =
ChEMBL = 1078154
SMILES = OH-.CCCCN+(CCCC)(CCCC)CCCC
Section2=
Section3=
Tetrabutylammonium hydroxide is the chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is employed as a solution in water or alcohols. It is a common base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu4NOH is more soluble in organic solvents. .

Preparation and reactions

Solutions of Bu4NOH are usually prepared in situ from butylammonium halides, Bu4NX, for example by reacting them with silver oxide or using an ion exchange resin. Attempts to isolate Bu4NOH induces Hofmann elimination, leading to Bu3N and 1-butene. Solutions of Bu4NOH are typically contaminated with Bu3N for this reason.
Treatment of Bu4NOH with a wide range of acids gives water and the other tetrabutylammonium salts: Bu4NOH + HX -> Bu4NX + H2O

Applications

Bu4NOH is a strong base that is used often under phase-transfer conditions to effect alkylations and deprotonations. Typical reactions include benzylation of amines and generation of dichlorocarbene from chloroform.
Bu4NOH can be neutralized with a variety of mineral acids to give lipophilic salts of the conjugate base. For example, treatment of Bu4NOH with disodium pyrophosphate, Na2H2P2O7, gives (Bu4N)3HP2O7, which is soluble in organic solvents. Similarly, neutralization of Bu4NOH with hydrofluoric acid affords an relatively water-free Bu4NF. This salt dissolves in organic solvents and is useful to desilylation.
Category:Tetrabutylammonium salts
Category:Hydroxides
 
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