quicksilver
International Hazard
Posts: 1820
Registered: 7-9-2005
Location: Inches from the keyboard....
Member Is Offline
Mood: ~-=SWINGS=-~
|
|
Picryl Chloride
Could common parachlorobenzene (moth balls, etc) be used in a synthesis of Picryl Chloride?
A straight forward synthesis exists but continually mentions chlorobenzene.
In the chemical industry what does the utilization of the term "para" mean in terms of the chemical's structure ("para"-formaldehyde,
parachlorobenzene), etc?
|
|
|
sparkgap
International Hazard
Posts: 1234
Registered: 16-1-2005
Location: not where you think
Member Is Offline
Mood: chaotropic
|
|
"para" in the case of "para-dichlorobenzene" means you have two chlorine atoms attached to benzene at positions 1 and 4 (the opposite corners, if you
have trouble visualizing).
The problem of making picryl chloride then is removing one of the chlorines so that you can put nitro groups at positions 2, 4, and 6. That, however,
is a pipe dream, I think. 
sparky (~_~)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
|
|
|
quicksilver
International Hazard
Posts: 1820
Registered: 7-9-2005
Location: Inches from the keyboard....
Member Is Offline
Mood: ~-=SWINGS=-~
|
|
In re-reading a related thread:
http://www.sciencemadness.org/talk/viewthread.php?tid=8027
It seems to be problematic. I had hoped there was a reasonable work-around. It's such a damn fine OTC source.
|
|
|
vulture
Forum Gatekeeper
Posts: 3330
Registered: 25-5-2002
Location: France
Member Is Offline
Mood: No Mood
|
|
You can remove one chlorine by reaction with one equivalent of Mg or BuLi. Then quench with water. It's an awful waste of material though.
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
|
|
|
chemrox
International Hazard
Posts: 2961
Registered: 18-1-2007
Location: UTM
Member Is Offline
Mood: LaGrangian
|
|
An eq of Mg? Is this making the Grignard and then hydrolizing? Terrible waste but can this even be done with PDB?
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
|
|
|
The_Davster
A pnictogen
Posts: 2861
Registered: 18-11-2003
Member Is Offline
Mood: .
|
|
Problem is, that the electron withdrawing nature of the chlorine only allows synthesis to 2,4 dinitrochlorobenzene. The third is almost imossible to
get on, short of using oleum and fuming nitric(IIRC, what is the chlorobenzene procedure you speak of?).
Luckily as illustrated in the pentryl thread, once the chlorine has been substituted off the 6 position is easier to nitrate.
|
|
|
quicksilver
International Hazard
Posts: 1820
Registered: 7-9-2005
Location: Inches from the keyboard....
Member Is Offline
Mood: ~-=SWINGS=-~
|
|
| Quote: | Originally posted by The_Davster
.... what is the chlorobenzene procedure you speak of?
|
Direct nitration using higher percentage acids was what I had seen. The concepts were all straight forward. I was hoping that the starting material
was available without attempting to work with liquid benzene.
|
|
|
vulture
Forum Gatekeeper
Posts: 3330
Registered: 25-5-2002
Location: France
Member Is Offline
Mood: No Mood
|
|
| Quote: |
An eq of Mg? Is this making the Grignard and then hydrolizing? Terrible waste but can this even be done with PDB? |
It works with a variety of organic halides, so I don't see why this wouldn't work. Usually the formation of the grignard reagent is easier if the
substrate is more electron poor.
One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
