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Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'CASNo_Ref') per [[WP:CHEMVALID|Chem/Drugbox validat...
 
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{{Chembox
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461284361
| verifiedrevid = 461284361
| ImageFile = Triton B.png
| ImageFile = Triton B.png
| ImageSize = 150px
| ImageSize = 160px
| ImageAlt = Skeletal formula of benzyltrimethylammonium hydroxide
| ImageAlt = Skeletal formula of benzyltrimethylammonium hydroxide
| ImageFile1 = Benzyltrimethylammonium-hydroxide-3D-balls.png
⚫
| IUPACName = ''N'',''N'',''N''-Trimethyl-1-phenylmethanaminium hydroxide
| ImageSize1 = 150
| OtherNames = Triton B, Trimethylbenzylammonium hydroxide
| ImageAlt1 = Ball-and-stick model of the benzyltrimethylammonium hydroxide ions
⚫
| Section1 = {{Chembox Identifiers
| IUPACName = Benzyl(trimethyl)azanium hydroxide
⚫
| CASNo_Ref = {{cascite|correct|??}}
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| OtherNames = Triton B, Trimethylbenzylammonium hydroxide, ''N'',''N'',''N''-Trimethyl-1-phenylmethanaminium hydroxide
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|Section1={{Chembox Identifiers
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 100-85-6
| CASNo = 100-85-6

⚫
| SMILES = C[N+](C)(C)Cc1ccccc1.[OH-]
| UNII_Ref = {{fdacite|changed|FDA}}
⚫
| PubChem = 66854
| UNII = 8P4488425W
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}


⚫
| SMILES = C[N+](C)(C)Cc1ccccc1.[OH-]
⚫
| PubChem = 66854
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 60218
| ChemSpiderID = 60218
| InChI = 1/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
| InChI = 1/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
| InChIKey = NDKBVBUGCNGSJJ-REWHXWOFAN
| InChIKey = NDKBVBUGCNGSJJ-REWHXWOFAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
| StdInChI = 1S/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NDKBVBUGCNGSJJ-UHFFFAOYSA-M
| StdInChIKey = NDKBVBUGCNGSJJ-UHFFFAOYSA-M
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=10|H=17|N=1|O=1
| C=10 | H=17 | N=1 | O=1
| Appearance = Liquid, clear, slightly yellow
| Appearance = Liquid, clear, slightly yellow
| Density = 0.95 g/mL
| Density = 0.95 g/mL
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility = Miscible in water }}
| Solubility = Miscible in water }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


'''Benzyltrimethylammonium hydroxide''', also known as '''Triton B''' or '''trimethylbenzylammonium hydroxide''', is an organic base. It is used in [[aldol condensation]] reactions and base-catalyzed [[dehydration reaction]]s.
'''Benzyltrimethylammonium hydroxide''', also known as '''Triton B''' or '''trimethylbenzylammonium hydroxide''', is a [[quaternary ammonium salt]] that functions as an organic base. It is usually handled as a solution in water or [[methanol]]. The compound is colourless, although the solutions often appear yellowish.<ref>Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. {{doi|10.1002/047084289X.rb079}}</ref> Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis.


== Sources ==
==Uses==
Together with the [[Benzyltriethylammonium hydroxide|benzyltriethylammonium]] salt, benzyltrimethylammonium hydroxide is a popular [[phase-transfer catalyst]].<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a19_293|chapter=Phase-Transfer Catalysis|year=2000|last1=Halpern|first1=Marc|isbn=3527306730}}</ref>

It is used in [[aldol condensation]] reactions and base-catalyzed [[dehydration reaction]]s. It is also used as a base in Ando's Z-selective variant of [[Horner–Wadsworth–Emmons reaction|Horner-Wadsworth-Emmons Olefination]] reactions.<ref>Chaturvedi, D., & Ray, S. (2006). Triton b catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatshefte fuer Chemie, 137. Retrieved from https://doi.org/10.1007%2Fs00706-005-0452-2 {{doi|10.1007/s00706-005-0452-2}}</ref>

Relative to tetramethylammonium hydroxide, benzyltriethylammonium hydroxide is more labile. In 6M NaOH at 160&nbsp;°C their half-lives are 61.9 and 4 h, respectively.<ref>{{cite journal |doi=10.1002/cssc.201403022|title=Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids|year=2015|last1=Marino|first1=M. G.|last2=Kreuer|first2=K. D.|journal=ChemSusChem|volume=8|issue=3|pages=513–523|pmid=25431246}}</ref>

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

<!--- After listing your sources please cite them using inline citations and place them after the information they cite. Please see [[WP:REFB]] for instructions on how to add citations. --->
==See also==
* http://www.chemcas.com/AnalyticalDetail.asp?pidx=1&id=19594&cas=100-85-6&page=490
* http://www.chemcas.com/AnalyticalDetail.asp?pidx=1&id=19594&cas=100-85-6&page=490
* Chaturvedi, D., & Ray, S. (2006). Triton b catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatshefte fuer Chemie, 137. Retrieved from http://www.springerlink.com/content/m48703268m3qw323/fulltext.pdf doi: 10.1007/s00706-005-0452-2


[[Category:Hydroxides]]
[[Category:Hydroxides]]
[[Category:Quaternary ammonium compounds]]
[[Category:Quaternary ammonium compounds]]
[[Category:Reagents for organic chemistry]]
[[Category:Reagents for organic chemistry]]
[[Category:Benzyl compounds]]

Latest revision as of 13:20, 20 January 2024

Benzyltrimethylammonium hydroxide
Skeletal formula of benzyltrimethylammonium hydroxide
Ball-and-stick model of the benzyltrimethylammonium hydroxide ions
Names
IUPAC name
Benzyl(trimethyl)azanium hydroxide
Other names
Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.632 Edit this at Wikidata
UNII
  • InChI=1S/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1 checkY
    Key: NDKBVBUGCNGSJJ-UHFFFAOYSA-M checkY
  • InChI=1/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
    Key: NDKBVBUGCNGSJJ-REWHXWOFAN
  • C[N+](C)(C)Cc1ccccc1.[OH-]
Properties
C10H17NO
Molar mass 167.252 g·mol−1
Appearance Liquid, clear, slightly yellow
Density 0.95 g/mL
Miscible in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Benzyltrimethylammonium hydroxide, also known as Triton B or trimethylbenzylammonium hydroxide, is a quaternary ammonium salt that functions as an organic base. It is usually handled as a solution in water or methanol. The compound is colourless, although the solutions often appear yellowish.[1] Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis.

Uses

[edit]

Together with the benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular phase-transfer catalyst.[2]

It is used in aldol condensation reactions and base-catalyzed dehydration reactions. It is also used as a base in Ando's Z-selective variant of Horner-Wadsworth-Emmons Olefination reactions.[3]

Relative to tetramethylammonium hydroxide, benzyltriethylammonium hydroxide is more labile. In 6M NaOH at 160 °C their half-lives are 61.9 and 4 h, respectively.[4]

References

[edit]
  1. ^ Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi:10.1002/047084289X.rb079
  2. ^ Halpern, Marc (2000). "Phase-Transfer Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_293. ISBN 3527306730.
  3. ^ Chaturvedi, D., & Ray, S. (2006). Triton b catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatshefte fuer Chemie, 137. Retrieved from https://doi.org/10.1007%2Fs00706-005-0452-2 doi:10.1007/s00706-005-0452-2
  4. ^ Marino, M. G.; Kreuer, K. D. (2015). "Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids". ChemSusChem. 8 (3): 513–523. doi:10.1002/cssc.201403022. PMID 25431246.

See also

[edit]
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