Open main menu
Home
Random
Recent changes
Special pages
Community portal
Preferences
About Wikipedia
Disclaimers
Incubator escapee wiki
Search
User menu
Talk
Dark mode
Contributions
Create account
Log in
Editing
Dimethylaniline
(section)
Warning:
You are not logged in. Your IP address will be publicly visible if you make any edits. If you
log in
or
create an account
, your edits will be attributed to your username, along with other benefits.
Anti-spam check. Do
not
fill this in!
==Reactions== Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.<ref>{{cite journal |doi=10.15227/orgsyn.019.0079 |title=P-Thiocyanatodimethylaniline |journal=Organic Syntheses |date=1939 |volume=19 |page=79|first1=R. Q. |last1=Brewster|first2=Wesley|last2=Schroeder }}</ref> It is [[nitration|nitrated]] to produce [[tetryl]], a derivative with four [[nitro compound|nitro]] groups which was once used as explosive. In acidic solution, the initial nitration gives 3-nitrodimethylaniline.<ref>{{cite journal |doi=10.15227/orgsyn.027.0062 |title=m-Nitrodimethylaniline |journal=Organic Syntheses |date=1947 |volume=27 |page=62|author=Howard M. Fitch }}.</ref> It reacts with [[n-Butyllithium|butyllithium]] to give the 2-lithio derivative. Electrophilic methylating agents like [[dimethyl sulfate]] attack the amine to give the quaternary ammonium salt:<ref>{{OrgSynth | | author = Jacques, J. and Marquet, A. | title = Selective Ξ±-Bromination of an Aralkyl Ketone with Phenyltrimethylammonium Tribromide: 2-Bromoacetyl-6-methoxynaphthalene and 2,2-Dibromoacetyl-6-Methoxynaphthalene | volume = 53 | pages = 111 | year = 1973 | doi = 10.15227/orgsyn.053.0111}}</ref> :C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>2</sub> +(CH<sub>3</sub>O)<sub>2</sub>SO<sub>2</sub> β C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>3</sub>CH<sub>3</sub>OSO<sub>3</sub> [[Diethylaniline]] and dimethylaniline are both used as acid-absorbing bases.
Edit summary
(Briefly describe your changes)
By publishing changes, you agree to the
Terms of Use
, and you irrevocably agree to release your contribution under the
CC BY-SA 4.0 License
and the
GFDL
. You agree that a hyperlink or URL is sufficient attribution under the Creative Commons license.
Cancel
Editing help
(opens in new window)