Sciencemadness Discussion Board

Naphthalene -> Acenaphthene

warteo - 15-4-2011 at 01:58

Hi,

I've been seeking a source of Acenaphthene to take advantage of its polyploidy inducing properties when seeds are treated with a solution of it. My search of various chemical suppliers has shown it to be more expensive than I'd like at around $100 per 100g. So instead of purchasing I'm wondering if it can be synthesized using common and inexpensive Naphthalene as a starting point? Or to illustrate, can the following be done reasonably easily?

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I'd be pleased to hear any ideas on how to go about this and more than that, I'd like to know more of the theory involved in selecting an approach. Hoping to learn more chemistry at the same time as gaining a valuable chemical for my experimental work with plants.

ScienceSquirrel - 15-4-2011 at 03:09

You would be looking at reacting 1,2 dibroethane in a Friedel Crafts reaction.
Reaction conditions would be quite critical or you would end up with a lot of glop or maybe even all glop.
A better procedure would be the reaction of oxalyl chloride to form the dione;

http://www.scientific.net/MSF.561-565.683

this would then be reduced to form acenapthene.

12332123 - 15-4-2011 at 03:53

If all you want is to induce polyploidy your best bet is probably autumn crocus extract, containing colchicine - Be careful, this is highly toxic.