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Author Topic: trimethylsulfonium bromide  (Read 156 times)

redcat

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trimethylsulfonium bromide
« on: March 19, 2011, 12:05:11 AM »
according the this post of SM: hxxp://www.sciencemadness.org/talk/viewthread.php?tid=15704#pid204634
TMSB can be easily prepared by the addition of Br2 to DMSO, with minimal cooling, and then used to methylate phenols.
this seems like it could easily substitute for more dangerous and inconvenient gaseous methylating agents, like MeI[1], in the methylations of vanillin and hydroquinone.

best of all, DMSO is less than $20 for a liter, and available OTC, along with all the necessary reagents to make liquid bromine in copious quantities!

[1]Methyl iodide is a liquid at room temperature.
« Last Edit: March 20, 2011, 09:16:33 AM by Enkidu »

Vesp

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Re: trimethylsulfonium bromide
« Reply #1 on: March 19, 2011, 01:06:33 AM »
Wow that is a great find thank you for sharing. Does it offer any synthetic disadvantages over other more dangerous methylating agents such as MeI?
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Enkidu

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Re: trimethylsulfonium bromide
« Reply #2 on: March 20, 2011, 06:44:02 AM »
^ High temperatures may be required.

This was already mentioned here,
http://127.0.0.1/talk/index.php/topic,187.msg19204.html#msg19204

psychexplorer

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Re: trimethylsulfonium bromide
« Reply #3 on: March 21, 2011, 03:47:45 AM »
Excellent. This made my whole week!

redcat

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Re: trimethylsulfonium bromide
« Reply #4 on: March 22, 2011, 03:03:03 AM »
The original writeup on SM uses polyethylene glycol, but that can be kind of a drag to get.
does anybody have any reasonable suggestions for a more common solvent?
would naphtha work? toluene?

carl_nnabis

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Re: trimethylsulfonium bromide
« Reply #5 on: May 29, 2013, 12:09:21 PM »
Quote from: teahead on May 28, 2013, 04:53:22 PM
Anyone know anything about DMSO shelf life? definite old 99% purity bottle that sat through hot and cold temps
Does it smell bad(dimethylsulfide)? Does it solidifie at the m.p.? If so it shoulf be still good and usable.
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