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.[1]
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.[1]
Treatment of Bu4NOH with a wide range of acids gives water and the other tetrabutylammonium salts:
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.[2] Similarly, neutralization of Bu4NOH with hydrofluoric acid affords an relatively water-free Bu4NF. This salt dissolves in organic solvents and is useful in desilylation.[3]
Referencesedit
^ abcBos, Mary Ellen (2004). "Tetrabutylammonium Hydroxide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rt017. ISBN0-471-93623-5..
^Woodside, A. B.; Huang, Z.; Poulter, C. D. (1993). "Trisammonium Geranyl Diphosphate". Organic Syntheses; Collected Volumes, vol. 8, p. 616.
^Kuwajima, I.; Nakamura, E.; Hashimoto, K. (1990). "Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene". Organic Syntheses; Collected Volumes, vol. 7, p. 512.
January 01, 1970
tetrabutylammonium, hydroxide, chemical, compound, with, formula, c4h9, 4noh, abbreviated, bu4noh, with, acronym, tbaoh, tbah, this, species, employed, solution, water, alcohols, common, base, organic, chemistry, relative, more, conventional, inorganic, bases,. 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 1 Tetrabutylammonium hydroxide Names Preferred IUPAC name N N N Tributylbutan 1 aminium hydroxide Other names TBAH TBAOH Identifiers CAS Number 2052 49 5 Y 3D model JSmol Interactive image ChEMBL ChEMBL1078154 Y ChemSpider 2005872 Y ECHA InfoCard 100 016 498 PubChem CID 2723671 UNII 68I858J9S1 Y CompTox Dashboard EPA DTXSID8062155 InChI InChI 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 YKey VDZOOKBUILJEDG UHFFFAOYSA M YInChI 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 1Key VDZOOKBUILJEDG REWHXWOFAE SMILES OH CCCC N CCCC CCCC CCCC Properties Chemical formula C 16H 37N O Molar mass 259 478 g mol 1 Solubility in water soluble Solubility soluble in most organic solvents Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesPreparation and reactions editSolutions 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 1 Treatment of Bu4NOH with a wide range of acids gives water and the other tetrabutylammonium salts Bu 4 NOH HX Bu 4 NX H 2 O displaystyle ce Bu4NOH HX gt Bu4NX H2O nbsp Applications editBu4NOH 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 1 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 2 Similarly neutralization of Bu4NOH with hydrofluoric acid affords an relatively water free Bu4NF This salt dissolves in organic solvents and is useful in desilylation 3 References edit a b c Bos Mary Ellen 2004 Tetrabutylammonium Hydroxide In Paquette Leo A ed Encyclopedia of Reagents for Organic Synthesis New York J Wiley amp Sons doi 10 1002 047084289X rt017 ISBN 0 471 93623 5 Woodside A B Huang Z Poulter C D 1993 Trisammonium Geranyl Diphosphate Organic Syntheses Collected Volumes vol 8 p 616 Kuwajima I Nakamura E Hashimoto K 1990 Silylation of Ketones with Ethyl Trimethylsilacetate Z 3 Trimethylsiloxy 2 Pentene Organic Syntheses Collected Volumes vol 7 p 512 Retrieved from https en wikipedia org w index php title Tetrabutylammonium hydroxide amp oldid 1181207556, wikipedia, wiki, book, books, library,
