“Tetrabutylammonium hydroxide”的意思、由来-开放百科全书

词条

Tetrabutylammonium hydroxide

释义

Reactions
Applications
References

{{chembox
| verifiedrevid = 470603420
| ImageFile=TBAH.PNG
| ImageSize=
| IUPACName=tetrabutylammonium hydroxide
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VDZOOKBUILJEDG-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=2052-49-5
| PubChem=2723671
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1078154
| SMILES = [OH-].CCCC[N+](CCCC)(CCCC)CCCC
}}
|Section2={{Chembox Properties
| C=16 | H=37 | N=1 | O=1
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}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]

Reactions

Attempted isolation of 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 + 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[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 to desilylation.^[3]

References

1. ^¹Bos, 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}}.
2. ^{{OrgSynth | author = Woodside, A. B.; Huang, Z.; Poulter, C. D. | title = Trisammonium Geranyl Diphosphate | collvol = 8 | collvolpages = 616 | year = 1993 | prep = cv8p0616}}
3. ^{{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}}

2 : Quaternary ammonium compounds|Hydroxides

随便看

开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。