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Author: Subject: Organic Nitrites?
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[*] posted on 10-10-2020 at 17:49
Organic Nitrites?

I cant find a damn thing about alkyl nitrites other than that about their biological activity.

I don’t condone spoonfeeding but I really don’t think it applies in my situation because I’ve looked far and wide. The SM library doesn’t have anything, all research papers only talk about their biological activity/toxicity, and there are almost no references to the use of organic nitrites as a reactant/precursor in organic synthesis.

All I’m able to assume based on the info I have is that they aren’t very stable.

I would like to know:

How good of a leaving group is the nitrite group?

How are organic nitrites formed(reaction mechanism)?

Are there any reactions that they are used in?(NOT the victor Meyer synthesis, that is INORGANIC nitrite SALTS - not compounds)

I honestly don’t see that much potential in organic nitrites. Maybe if you switched up the victor Mayer synthesis and reacted and alkyl nitrite with an iodide salt something would happen, but I don’t see any reason to reinventing the wheel.

I have to order more sodium nitrite, so I can’t actually do any experiments atm, but that is my hope for the future. in the meantime, I’d like to get some useful reference material. If anyone knows more about organic nitrites than me, I’d really appreciate if you would drop what you know somewhere in this topic.

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[*] posted on 10-10-2020 at 17:59

i occasionally whip up a dab of ethyl nitrite (strictly for research purposes LMAO), and no, it does not keep well. But, I don't bother with the fridge, dark bottle etc.

Get my nitrite from Duda Diesel.

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Corrosive Joeseph
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[*] posted on 10-10-2020 at 18:28

Quote: Originally posted by chemist1243  

Are there any reactions that they are used in?


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Chemi Pharma
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[*] posted on 10-10-2020 at 23:50

Preparation of sodium azide from n-butyl nitrite and hydrazine hydrate

Forty to forty-three grams of sodium hydroxide are dissolved in 500 ml of absolute ethyl alcohol by warming. The solution is cooled and either filtered through a sintered glass funnel or decanted to remove insoluble impurities. To the clear filtrate in a one-liter flask fitted with a reflux condenser (a ground-glass type is preferable) are added 60 g of 85 % hydrazine hydrate. The mixture is warmed gently on a steam bath and then 15 g of freshly distilled n-butyl nitrite are added through the condenser. The steam bath is removed and then 110 g more of n-butyl nitrite are added as before at such a rate that spontaneous refluxing is maintained. The sodium azide precipitates during the procedure. To ensure completion of the reaction the flask and contents are heated 15-30 minutes after the addition. After cooling in ice, the sodium azide is suction-filtered and washed, first with four 25 ml portions of ice-cold absolute alcohol, then with two similar volumes of ether. The white salt is dried in warm air yielding 50-55 g of sodium azide.

Inorganic laboratory preparations, by G. G. Schlessinger, 28-29, 1962
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[*] posted on 12-10-2020 at 01:16

Preparation of dimethylglyoxine from butanone and butyl nitrite then hydroxylammonium chloride
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