Tetrabutylammonium hydroxide

Tetrabutylammonium hydroxide

chembox new
ImageFile=TBAH.pngImageSize=
IUPACName=tetrabutylammonium hydroxide
OtherNames=
Section1=Chembox Identifiers
CASNo=
PubChem=2723671
SMILES=CCCC [N+] (CCCC)(CCCC)CCCC. [OH-]

Section2=Chembox Properties
C=16 | H=37 | N=1 | O=1
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=

Section3=Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Tetrabutylammonium hydroxide is the chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is not readily obtainable as a pure compound, but it employed as a solution in water or alcohols. It is commonly used as a base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu4NOH is more soluble in organic solvents. Attempted isolation of pure Bu4NOH induces Hofmann elimination, leading to Bu3N and 1-butene. Solutions of Bu4NOH are typically contaminated with Bu3N for this reason. [Bos, M. E. "Tetra-n-butylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.]

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)3 [HP2O7] , which is soluble in organic solvents. [OrgSynth | author = Woodside, A. B.; Huang, Z.; Poulter, C. D. | title = Trisammonium Geranyl Diphosphate | collvol = 8 | collvolpages = 616 | year = 1993 | prep = cv8p0616] Similarly, neutralization of Bu4NOH with hydrofluoric acid affords Bu4NF. This salt dissolves in organic solvents and is useful to desilylation. [OrgSynth | author = Kuwajima, I.; Nakamura, E. Hashimoto, K. | title = Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene | collvol = 7 | collvolpages = 512 | year = 1990 | prep = CV7P0512]

References


Wikimedia Foundation. 2010.

Игры ⚽ Нужно сделать НИР?

Look at other dictionaries:

  • Organic base — Acids and Bases Acid dissociation constant Acid base extraction Acid–base reaction Acid–base titration Dissociation constant Acidity function Buffer sol …   Wikipedia

  • Tetrabutylammoniumhydroxid — Strukturformel Allgemeines Name Tetrabutylammoniumhydroxid Summenformel …   Deutsch Wikipedia

  • Caesium chloride — Caesium chloride …   Wikipedia

  • Dichlorocarbene — Dichlorocarbene …   Wikipedia

  • Oligonucleotide synthesis — is the chemical synthesis of relatively short fragments of nucleic acids with defined chemical structure (sequence). The technique is extremely useful in current laboratory practice because it provides a rapid and inexpensive access to custom… …   Wikipedia

  • Williamson ether synthesis — The Williamson ether synthesis was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction. This reaction is important in the history of organic chemistry… …   Wikipedia

  • Diallyl disulfide — Diallyl disulfide …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”