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Author Topic: Acetonitrile  (Read 245 times)

kidkemist

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Acetonitrile
« on: February 16, 2012, 01:38:36 PM »
First time post! Just wondering if anyone knew where I could legally buy acetonitrile in Victoria, Aus.
Sorry if this has already been posted =/

Thanks guys much appreciated.

fresh1

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Re: Acetonitrile
« Reply #1 on: February 17, 2012, 04:11:34 AM »
hey bro just a quick heads up , we dont 'do' sources here AT ALL :o

please read the rules, questions like this will get you banned
(matey there are PLENTY  of LE on this site too, and information like that goes to them too, this is why things like this are NOT DISCUSSED)

welcome, READ THE RULES and enjoy/be good ;)
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kidkemist

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Re: Acetonitrile
« Reply #2 on: February 17, 2012, 07:38:49 AM »
Thanks for the heads up mate.

Sedit

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Re: Acetonitrile
« Reply #3 on: February 17, 2012, 05:58:24 PM »
We are semi ok with sources as long as its not abused however we are a chemistry for so please stick to synthetic discussion.
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fresh1

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Re: Acetonitrile
« Reply #4 on: February 18, 2012, 02:58:27 AM »
how do you mean "semi ok with sources?"  does it depend on what is being sourced, or sharing sources via pm or....?

I thought listing any sources here was a primary no no!
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lugh

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Re: Acetonitrile
« Reply #5 on: February 18, 2012, 04:37:54 PM »
Quote
we are a chemistry for so please stick to synthetic discussion.

Nitrile synthesis. Dehydration of amides by silazanes, chlorosilanes, alkoxysilanes, and aminosilanes

William E. Dennis
J. Org. Chem., 1970, 35 (10), pp 3253–3255
DOI: 10.1021/jo00835a016

is attached  8)
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Sedit

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Re: Acetonitrile
« Reply #6 on: February 19, 2012, 02:22:14 AM »
Quote from: fresh1 on February 18, 2012, 02:58:27 AM
how do you mean "semi ok with sources?"  does it depend on what is being sourced, or sharing sources via pm or....?

I thought listing any sources here was a primary no no!
without derailing the thread to much, we used to have no problem with sourcing back when our member base had common sense however as we grow larger we have to become more strict because it seems the general population dont know whats best for themselves
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!

fresh1

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Re: Acetonitrile
« Reply #7 on: February 19, 2012, 07:58:11 AM »
fair enough, thanx for the reply.....yeah one thing which has always appealed here was the general level of member smarts, sad to hear its been diluted
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akcom

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Re: Acetonitrile
« Reply #8 on: February 21, 2012, 02:51:24 AM »
Is acetonitrile really that heavily watched?  Its such a common solvent...

no1uno

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Re: Acetonitrile
« Reply #9 on: February 21, 2012, 10:04:45 PM »
General rule of thumb - ALL solvents are watched in Oz, we have the worlds highest rate of Amphetamine and substituted Amphetamine use at present and pigs are getting more and more funds and more and more powers. That said, you can still source shit instead of making it, just be aware that pretty much anyone who chooses the first option is taking risks that never seem to pan out well.
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atara

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Re: Acetonitrile
« Reply #10 on: March 18, 2012, 04:53:40 AM »
Iodine will oxidize beta-alanine to mandelomononitrile. Alpha-cyanocarboxylic acids of this sort usually decarboxylate easily, in this case producing the desired acetonitrile.

That would definitely be the first thing I'd try. If iodine availability is an issue, peroxide may be an effective co-oxidant.

The issue that springs to mind is that in a basic condition the alpha carbon may deprotonate, rendering it susceptible to oxidation, so neutral or acidic conditions are preferable. This disqualifies most common bleaches, which would not be good co-oxidants.
« Last Edit: March 18, 2012, 05:11:49 AM by atara »

Vesp

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Re: Acetonitrile
« Reply #11 on: March 18, 2012, 05:09:39 AM »
Quote from: atara on March 18, 2012, 04:53:40 AM
Iodine will oxidize beta-alanine to mandelomononitrile. Alpha-cyanocarboxylic acids of this sort usually decarboxylate easily, in this case producing the desired acetonitrile.

That would definitely be the first thing I'd try. If iodine availability is an issue, peroxide or hypochlorite may be an effective co-oxidant.

Would other halogens work, such as the more available bromide?
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atara

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Re: Acetonitrile
« Reply #12 on: March 18, 2012, 05:18:02 AM »
Quote from: Vesp on March 18, 2012, 05:09:39 AM
Quote from: atara on March 18, 2012, 04:53:40 AM
Iodine will oxidize beta-alanine to mandelomononitrile. Alpha-cyanocarboxylic acids of this sort usually decarboxylate easily, in this case producing the desired acetonitrile.

That would definitely be the first thing I'd try. If iodine availability is an issue, peroxide or hypochlorite may be an effective co-oxidant.

Would other halogens work, such as the more available bromide?

The reaction has not been reported with bromine. In PiHKAL we see that bromine reacts very slowly with amines, if at all whereas the use of iodine necessitates a phthalimide protecting group. The conversion is detailed here:

http://www.sciencedirect.com/science/article/pii/S0040402007009738

I believe the reason iodine works is the relative stability of (electrophilic) I+ in contrast to Br+ and Cl+ which are essentially never observed except as BrO- and ClO-.

However, bromine can possibly be used as a co-oxidant with a catalytic amount of potassium iodide.

Vesp

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Re: Acetonitrile
« Reply #13 on: March 18, 2012, 05:33:03 AM »
Quote
However, bromine can possibly be used as a co-oxidant with a catalytic amount of potassium iodide.

That would be good. :)

Though, I do doubt the practicality of that over all method and I'd bet it would be easier/better to just buy the acetonitrile? Is it regulated at all?
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Balkan Bonehead

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Re: Acetonitrile
« Reply #14 on: March 19, 2012, 12:58:10 AM »
Why not oxidize regular alanine with TCCA?

java

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Re: Acetonitrile
« Reply #15 on: March 19, 2012, 02:53:09 AM »
Reference Information


Alkaline Bromine Oxidation of Amino Acids and Peptides:
Formation of a-Ketoacyl Peptides and Their Cleavage by Hydrogen Peroxide

Alanine  to acetonitrile...yield 70%

Note Simple bromide salts (such as sodium bromide) are also sometimes used in hot tubs and spas as mild germicidal agents, using the action of an added oxidizing agent (such as hydrogen peroxide) to generate in situ hypobromite, in a similar fashion to the action of peroxidase on bromide in eosinophils.
« Last Edit: March 19, 2012, 02:57:34 AM by java »
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