Tetrabutylammonium hydroxide: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 07:01, 11 August 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wiki← Previous edit		Latest revision as of 02:52, 12 October 2024 edit undoSwinub (talk \| contribs)Extended confirmed users66,836 editsm →Applications: Grammar
(23 intermediate revisions by 21 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
	\| verifiedrevid = ~~444217565~~		\| verifiedrevid = 470603420
	\|ImageFile=TBAH.PNG		\| ImageFile = TBAH.PNG
	\|ImageSize=		\| ImageSize =
			\| PIN = ''N'',''N'',''N''-Tributylbutan-1-aminium hydroxide
	\|IUPACName=tetrabutylammonium hydroxide
	\|OtherNames=		\| OtherNames = TBAH, TBAOH
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 2005872		\| 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		\| 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
Line 15:		Line 15:
	\| StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M		\| StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo=2052-49-5		\| CASNo = 2052-49-5
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| PubChem=2723671
			\| UNII = 68I858J9S1
⚫	\| ~~ChEMBL_Ref~~ = {{~~ebicite~~\|correct\|~~EBI~~}}
		⚫	\| PubChem = 2723671
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 1078154		\| ChEMBL = 1078154
	\| SMILES = .CCCC(CCCC)(CCCC)CCCC		\| SMILES = .CCCC(CCCC)(CCCC)CCCC
	}}		}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| C=16 \| H=37 \| N=1 \| O=1		\| C=16 \| H=37 \| N=1 \| O=1
	\| Appearance=		\| Appearance=
	\| Density=		\| Density=
	\| MeltingPt=		\| MeltingPt=
	\| BoilingPt=		\| BoilingPt=
	\| Solubility=		\| Solubility= soluble
			\| SolubleOther = soluble in most organic solvents
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}
	'''Tetrabutylammonium hydroxide''' is the ] with the formula (C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>NOH, abbreviated Bu<sub>4</sub>NOH 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 ]s. It is ~~commonly~~ ~~used as a~~ base in ]. Relative to more conventional inorganic bases, such as ] and ], Bu<sub>4</sub>NOH is more soluble in organic solvents. ~~Attempted isolation of pure Bu~~<~~sub>4</sub>NOH~~ ~~induces ], leading to Bu<sub~~>~~3</sub>N~~ ~~and ]. Solutions of Bu<sub>4</sub>NOH are typically contaminated with Bu<sub>3</sub>N for this reason.<ref>~~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~~.</ref>		'''Tetrabutylammonium hydroxide''' is the ] with the formula (C<sub>4</sub>H<sub>9</sub>)<sub>4</sub>NOH, abbreviated Bu<sub>4</sub>NOH with the acronym '''TBAOH''' or '''TBAH'''. This species is employed as a solution in water or ]s. It is a common base in ]. Relative to more conventional inorganic bases, such as ] and ], Bu<sub>4</sub>NOH is more soluble in organic solvents.<ref name=eEROS>{{cite book\|last=Bos\|first=Mary Ellen\|chapter=Tetrabutylammonium Hydroxide\|title=Encyclopedia of Reagents for Organic Synthesis\|editor-last=Paquette\|editor-first=Leo A.\|year=2004\|publisher=J. Wiley & Sons\|location=New York\|doi=10.1002/047084289X.rt017\|isbn=0-471-93623-5 }}.</ref>

			==Preparation and reactions==
			Solutions of Bu<sub>4</sub>NOH are usually prepared ''in situ'' from butylammonium halides, Bu<sub>4</sub>NX, for example by reacting them with ] or using an ]. Attempts to isolate Bu<sub>4</sub>NOH induces ], leading to Bu<sub>3</sub>N and ]. Solutions of Bu<sub>4</sub>NOH are typically contaminated with ] for this reason.<ref name=eEROS/>

			Treatment of Bu<sub>4</sub>NOH with a wide range of acids gives water and the other ] salts: <chem>Bu4NOH + HX -> Bu4NX + H2O</chem>

	==Applications==		==Applications==
	Bu<sub>4</sub>NOH is a strong base that is used often under ] conditions to effect ]s and ]s. Typical reactions include ]ation of amines and generation of ] from ].		Bu<sub>4</sub>NOH is a strong base that is used often under ] conditions to effect ]s and ]s. Typical reactions include ]ation of amines and generation of ] from ].<ref name=eEROS/>

	Bu<sub>4</sub>NOH can be ]d with a variety of ]s to give lipophilic salts of the ]. For example, treatment of Bu<sub>4</sub>NOH with ], Na<sub>2</sub>H<sub>2</sub>P<sub>2</sub>O<sub>7</sub>, gives (Bu<sub>4</sub>N)<sub>3</sub>, which is soluble in organic solvents.<ref>{{OrgSynth \| author = Woodside, A. B.; Huang, Z.; Poulter, C. D. \| title = Trisammonium Geranyl Diphosphate \| collvol = 8 \| collvolpages = 616 \| year = 1993 \| prep = cv8p0616}}</ref> Similarly, neutralization of Bu<sub>4</sub>NOH with ] affords ]. This salt dissolves in organic solvents and is useful to ].<ref>{{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}}</ref>		Bu<sub>4</sub>NOH can be ]d with a variety of ]s to give lipophilic salts of the ]. For example, treatment of Bu<sub>4</sub>NOH with ], Na<sub>2</sub>H<sub>2</sub>P<sub>2</sub>O<sub>7</sub>, gives (Bu<sub>4</sub>N)<sub>3</sub>, which is soluble in organic solvents.<ref>{{OrgSynth \|author=Woodside, A. B. \|author2=Huang, Z. \|author3=Poulter, C. D. \| title = Trisammonium Geranyl Diphosphate \| collvol = 8 \| collvolpages = 616 \| year = 1993 \| prep = cv8p0616}}</ref> Similarly, neutralization of Bu<sub>4</sub>NOH with ] affords a relatively water-free ]. This salt dissolves in organic solvents and is useful in ].<ref>{{OrgSynth \|author=Kuwajima, I. \|author2=Nakamura, E. \|author3=Hashimoto, K. \| title = Silylation of Ketones with Ethyl Trimethylsilacetate: (Z)-3-Trimethylsiloxy-2-Pentene \| collvol = 7 \| collvolpages = 512 \| year = 1990 \| prep = CV7P0512}}</ref>

	==References==		==References==
	<references/>		<references/>

	]		]
			]

	]

Latest revision as of 02:52, 12 October 2024

Tetrabutylammonium hydroxide
Names

Preferred IUPAC name N,N,N-Tributylbutan-1-aminium hydroxide
Other names TBAH, TBAOH
Identifiers
CAS Number	2052-49-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1078154
ChemSpider	2005872
ECHA InfoCard	100.016.498
PubChem CID	2723671
UNII	68I858J9S1
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-1Key: VDZOOKBUILJEDG-UHFFFAOYSA-M 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-1Key: VDZOOKBUILJEDG-REWHXWOFAE
SMILES .CCCC(CCCC)(CCCC)CCCC
Properties
Chemical formula	C₁₆H₃₇NO
Molar mass	259.478 g·mol
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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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: ${\ce {Bu4NOH + HX -> Bu4NX + H2O}}$

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)₃, which is soluble in organic solvents. Similarly, neutralization of Bu₄NOH with hydrofluoric acid affords a relatively water-free Bu₄NF. This salt dissolves in organic solvents and is useful in desilylation.

References

^ Bos, 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. 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.

Categories: