can any body sugest me how to make 2 nitro diphenyl sulfideDJF90 - 14-2-2010 at 10:27
Its fairly simple to make but I wouldnt want to use what I have in mind without a fumehood. Out of interest what do you want it for? JohnWW - 14-2-2010 at 12:40
The stuff is both an aromatic nitro-compound and an aromatic sulfide, so it may be the basis of a stink bomb!
P.S. http://www.orgsyn.org is likely to have have something on the synthesis of compounds of this type.
[Edited on 15-2-10 by JohnWW]Nicodem - 14-2-2010 at 15:30
Oh please JohnWW, do we have to read such comments?
Fresher_007, organic topics go to Organic section, but referenceless organic topics usually go to Beginnings, so there you go. I'll give you a few
advices. If you are up to useful replies, you might first try to explain why you are not pleased with the literature preparations. You should then
cite a few typical ones so that other members don't waste time proposing ideas already described elsewhere. You can only obtain as much useful replies
as much useful information you provide in posing the question.Sandmeyer - 14-2-2010 at 17:02
(2-nitro-phenyl)-phenyl ether
To a stirred solution of phenol (9.4g, 0.1mol) in 30 mL DMSO, KOH (5.6 g, 0.1moL) was added. The mixture was stirred for 30 min. and then a solution
of 1-chloro-2-nitro-benzene (15.7g, 0.1mol) in 10 mL DMSO was added drop wise during a period of 5 min. at room temperature. The resulted mixture was
stirred for another 5 h at 90°C. After cooling to room temperature, the reaction mixture was poured into 200 mL water. The product was abstracted
with ethyl ether (50mL×3). The combined ether was washed with water (50mL×5), dried with Na2SO4, and the solvent was removed in vacuo to give
product as oil (20.3g) in 94% yield, which was used without further purification. 1H NMR(300MHz, CDCl3): 􀈨 7.93 (dd, 1H, J = 1.5, 8.1 Hz,
Ar-H); 7.49 (dt, 1H, J = 1.5, 7.5 Hz, Ar-H); 7.35-7.40 (m, 2H, Ph-H); 7.15-7.21 (m, 2H, Ph-H); 6.98-7.06 (m, 3H, Ph-H).
(2-nitro-phenyl)-phenyl sulfide (3e)
Following above procedure, benzenethiol (11.0 g, 0.1mol), KOH (5.6 g, 0.1mmol) and 1-chloro-2-nitro-benzene( 15.7g, 0.1mol) were used. 3e (22.4g) was
obtained as a yellow powder in 96% yield. 1H NMR (300MHz, CDCl3): 􀈨 8.21 (dd, J = 1.2, 8.1Hz, 1H, Ar
I copied this that from the supporting info to the article: Organometallics, 2006, 25 (13), pp 3259–3266
The stuff is both an aromatic nitro-compound and an aromatic sulfide, so it may be the basis of a stink bomb!
You are raising an important point - the stench. I don't know about the product but the starting material (thiophenol) is a record-breaking "stink
bomb". One must be very cautios when working with thiophenol. I would not use it without efficient ventilation, it is enough to simply open the flask
to have a persisting stench in the room. Nicodem - 15-2-2010 at 01:30
Thiophenol stinks terribly, but if you work in a fumehood it is no problem (except if you make some stupid mistakes, like taking out the used pipette
or something dumb like that). The work up can be unpleasant as it takes much care to do extractions without bringing the stench out of the fumehood. I
used thiophenol several times and with some care and practice managed to do it without even smelling it. It is however a reagent relatively sensitive
for oxidation by air, particularly in basic solutions, so the use of inert atmosphere is suggested.
Luckily in this case the product is probably nearly odourless.
