4-Methylbenzyltrimethylammonium hydroxide

4-Methylbenzyltrimethylammonium hydroxide is a quaternary ammonium compound with the formula C₁₁H₁₈N⁺OH⁻. It can be synthesized by reacting 4-methylbenzyl bromide with triethylamine, followed by stirring with silver oxide in water.^[1]

4-Methylbenzyltrimethylammonium hydroxide

Names
Other names p-Methylbenzyltrimethylammonium hydroxide
Identifiers
CAS Number	43011-61-6 Y
3D model (JSmol)	Interactive image
PubChem CID	12324565
InChI InChI=1S/C11H18N.H2O/c1-10-5-7-11(8-6-10)9-12(2,3)4;/h5-8H,9H2,1-4H3;1H2/q+1;/p-1 Key: BHZSLQZBUUWFED-UHFFFAOYSA-M
SMILES [OH-].C=1C=C(C=CC1C)C[N+](C)(C)C
Properties
Chemical formula	C11H19NO
Molar mass	181.279 g·mol−1
Boiling point	dec.
Related compounds
Related compounds	Benzyltrimethylammonium hydroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reactions

When heated with phenothiazine in toluene, it undergoes Hofmann elimination to form [2.2]Paracyclophane.^[1]

Paracycloheterophanes can be obtained by heating it with other quaternary ammonium hydroxides (e.g. with (5-methyl-2-thienylmethyl)trimethylammonium hydroxide to form [2.2]paracyclo(2,5)thiophenophane).^[2]