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Offline AlphaScent

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NBS question
« on: August 23, 2012, 04:54:55 PM »
In the lab today one of my colleagues did not weight our cylinder of 1,3-butadiene correctly. In turn, I came up short (by half) for my synthesis of 1-bromo-but-3-ene-2-ol.  The reaction calls for water, which is terrible for the NBS.   The water had yet to be added though.  The NBS was only stirring in ether; what do you think my chances are of recovering and using the NBS tomorrow with out any trouble??  Any experience with this?  I know theoretically it should be fine, but I was wondering about experience with this.  Thank you very much in advance!!

Also, it is stored under argon.

Thanks again,

Cheers
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Offline discodermolide

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Re: NBS question
« Reply #1 on: August 24, 2012, 12:08:37 AM »
In the lab today one of my colleagues did not weight our cylinder of 1,3-butadiene correctly. In turn, I came up short (by half) for my synthesis of 1-bromo-but-3-ene-2-ol.  The reaction calls for water, which is terrible for the NBS.   The water had yet to be added though.  The NBS was only stirring in ether; what do you think my chances are of recovering and using the NBS tomorrow with out any trouble??  Any experience with this?  I know theoretically it should be fine, but I was wondering about experience with this.  Thank you very much in advance!!

Also, it is stored under argon.

Thanks again,

Cheers

It should be OK to re-use.
If in doubt just use fresh material.
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Offline james_a

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Re: NBS question
« Reply #2 on: August 24, 2012, 11:57:53 AM »
In the lab today one of my colleagues did not weight our cylinder of 1,3-butadiene correctly. In turn, I came up short (by half) for my synthesis of 1-bromo-but-3-ene-2-ol.  The reaction calls for water, which is terrible for the NBS.   The water had yet to be added though.  The NBS was only stirring in ether; what do you think my chances are of recovering and using the NBS tomorrow with out any trouble??  Any experience with this?  I know theoretically it should be fine, but I was wondering about experience with this.  Thank you very much in advance!!

Also, it is stored under argon.

Thanks again,

Cheers

What you mean about water being terrible for the NBS? it's usually recrystallized from hot water.

Offline zoork34

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Re: NBS question
« Reply #3 on: August 24, 2012, 03:28:23 PM »
If the NBS was only stirring in ether, just let the ether evaporate and you will have your dry NBS back

Offline Nescafe

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Re: NBS question
« Reply #4 on: August 28, 2012, 08:34:55 PM »
In the lab today one of my colleagues did not weight our cylinder of 1,3-butadiene correctly. In turn, I came up short (by half) for my synthesis of 1-bromo-but-3-ene-2-ol.  The reaction calls for water, which is terrible for the NBS.   The water had yet to be added though.  The NBS was only stirring in ether; what do you think my chances are of recovering and using the NBS tomorrow with out any trouble??  Any experience with this?  I know theoretically it should be fine, but I was wondering about experience with this.  Thank you very much in advance!!

Also, it is stored under argon.

Thanks again,

Cheers

What you mean about water being terrible for the NBS? it's usually recrystallized from hot water.

I was also under the impression that water is pretty bad and as it has an removable hydrogen. This is one of the reasons why it is done in carbon tetrachloride and not lets say in methanol. Correct me if I am wrong but if you have loads of water around would it not be possible to generate other reactive radical species from water like OH radical and H radical?

Offline discodermolide

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Re: NBS question
« Reply #5 on: August 28, 2012, 09:17:24 PM »
In the lab today one of my colleagues did not weight our cylinder of 1,3-butadiene correctly. In turn, I came up short (by half) for my synthesis of 1-bromo-but-3-ene-2-ol.  The reaction calls for water, which is terrible for the NBS.   The water had yet to be added though.  The NBS was only stirring in ether; what do you think my chances are of recovering and using the NBS tomorrow with out any trouble??  Any experience with this?  I know theoretically it should be fine, but I was wondering about experience with this.  Thank you very much in advance!!

Also, it is stored under argon.

Thanks again,

Cheers

What you mean about water being terrible for the NBS? it's usually recrystallized from hot water.

I was also under the impression that water is pretty bad and as it has an removable hydrogen. This is one of the reasons why it is done in carbon tetrachloride and not lets say in methanol. Correct me if I am wrong but if you have loads of water around would it not be possible to generate other reactive radical species from water like OH radical and H radical?

The reason CCl4 is used is that succinamide is totally insoluble in that solvent so work-up is easy, filter and evaporate.
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