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+ Synthetic organic chemistry
+ Organic synthesis
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Lauren Barcas

How to purify/recrystallize N-chlorosuccinimide?

Brian O'Sullivan  Follow

Hello,

On topic: I haven't tried it, but NCS appears to be possible to recrystallize from warm glacial Acetic acid, cooled down, filtered and then washed with i) glacial acetic acid ii) hexane.

DOI: 10.1002/047084289X.rc145.pub2

Off topic: afaik doesn't mean "fake", it is an acrononym/internet slang for "as far as I know".

Have a good day,

JR


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Bryan Katz  Follow

Super easy to recrystallize from acetic acid, just heat to 70C with a minimal amount to dissolve it, then cool, filter and pump. You can probably also use water, since that is the best way to recrystallize NBS. Again, just make sure you pump long enough to get all the solvent out.


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Adam Jacholkowski  Follow

dear Yogesh :as u know the commercial reagent acquires a light yellow color It is easily recrystallized from acetic acid: rapidly dissolve 200 g of impure sample in 1 L preheated glacial acetic acid at 65–70 °C (3–5 min); cool to 15–20 °C to effect crystallization; filter through a Buckner funnel and wash the white crystals once with glacial acetic acid and twice with hexane; dry in freeze dryer .u will got a pure sample .
see the link:http://onlinelibrary.wiley.com/


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Christopher Hauck  Follow

NBS is crystallized from hot water cooling it to RT slowly. NCS should work just the same. Removal of residual water may take 48 h on a good vacuum pump.
Crystallisation form acetic acid results in trace impurity of acid, which may have an impact on reaction kinetics and even pathways (in the case of NBS)


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Allan Emery  Follow

From acetic acid it is possible to purify ncs


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Chaw Tin Zar Maung  Follow

NCS may be crystallized with acetic acid I have recrystallized NBS with same route


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Bubba Bear Huntington  Follow

Kaufman,
In my personal experience with NCS I used it as is from commercial sources. I wonder if you have ever performed the above literature method and found that it is fake as you claim. Please, let me know because I am trying to help my colleagues in the field by whatever in hand and many of my replies are based on my experience and supported by literature survey. By the way "fake" is a word that does not fit in my dictionary.
Thanks


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Daniel Iyamuremye  Follow

it is possible to purify N-Chloro and N-bromosuccinimide by dissolving in CH2Cl2 or CHCl3, contrifugating to separe the almost unsoluble succinimide and Evaporation of the solvent. The remainding succinimide in solution is low.


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David Sandiford  Follow

Rapidly crystd from *benzene, or glacial acetic acid and washed well with water then dried in vacuo. [Phillips and Cohen J Am Chem SOC 108 2023 1986.
From: PURIFICATION OF LABORATORY CHEMICALS - Christina Li Lin Chai , W.L.F Armarego

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Alex Gossland  Follow

You can purifyn-chorosuccinimide from Dimethyl formamide


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