argox120
Harmless
Posts: 22
Registered: 3-1-2022
Member Is Offline
|
|
Looking for 2 nitroaniline
Hello, can anybody please point me in the right direction, i need 2 nitro aniline cas 88-74-4 to form an imine derivative of a substance, hope yall
can help me
|
|
|
chempyre235
Hazard to Self
Posts: 57
Registered: 21-10-2024
Location: Between Niobium and Technetium
Member Is Offline
|
|
What sources have you searched already? 2-Nitroaniline should be relatively simple to make for the amateur. According to Wikipedia, it can be made
from acetaminophen. Please, use your search engine, and stop asking to be spoonfed. Do your own research first.
|
|
|
argox120
Harmless
Posts: 22
Registered: 3-1-2022
Member Is Offline
|
|
clueless person, how can 2 nitroaniline be made from acetaminophen which has a hydroxyl group para to the aniline. since you are so wise here.
|
|
|
chempyre235
Hazard to Self
Posts: 57
Registered: 21-10-2024
Location: Between Niobium and Technetium
Member Is Offline
|
|
I apologize. I meant acetanilide, not acetaminophen.
|
|
|
bnull
National Hazard
Posts: 596
Registered: 15-1-2024
Location: Home
Member Is Offline
Mood: Sneezing like there's no tomorrow. Stupid cat allergy.
|
|
Quote: Originally posted by argox120  | | Hello, can anybody please point me in the right direction, i need 2 nitro aniline cas 88-74-4 to form an imine derivative of a substance, hope yall
can help me |
Do you want to buy or to make it? If the former, you can try @mario840.
|
|
|
Keras
International Hazard
Posts: 1013
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline
|
|
One way I see is, starting from aniline, make acetanilide (e.g. with zinc and acetic acid rather than the more expensive and difficult to get acetic
anhydride), then nitrate the acetanilide the standard way, producing a mixture of o- and p-nitroacetanilide. Hydrolyse the 'acetate' moiety by
refluxing in dilute acid to get a mixture of o- and p- nitroaniline, which can be separated on a chromatographic column filled with alumina using
toluene as eluent (easy, two yellow rings, o- comes first).
Because of steric hinderance, the yield of o-nitroaniline is not that great, much less than p-nitroaniline, but eh. Maybe you could sulphonate the
acetanilide, which would block the para position before nitrating. Then on hydrolysis both the sulphonate and the acetate group would be released,
giving pure o-nitroaniline. No promise, though.
Aniline needs be protected from protonation by the acid nitrating mixture, otherwise you end up with m-nitroaniline.
[EDIT: Apparently, there’s an easy separation process whereby the mixture o-/p- is dissolved in methanol. On cooling, p- will crystallise, while o-
stays in solution and can be isolated later.]
[Edited on 26-3-2025 by Keras]
|
|
|
chempyre235
Hazard to Self
Posts: 57
Registered: 21-10-2024
Location: Between Niobium and Technetium
Member Is Offline
|
|
Orgsyn has a synthesis using the sulfonated derivative followed by hydrolysis.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
