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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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July 1, 2014

Corrosion Using Selectfluor?

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Posted by Derek

Here's a question for those of you who've used Selectfluor (Air Products trademark), the well-known fluorinating reagent. I've had an email from someone at Sigma-Aldrich, wondering if people have noticed corrosion problems with either glass or stainless steel when using or storing the reagent. I've hardly used it myself, so I don't have much to offer, but I figured that there was a lot of chemical experience out in the blog's readership, and someone may have something to add.

Comments (12) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. Anonymous on July 1, 2014 7:50 AM writes...

Nope!

Sufficient ?

Permalink to Comment

2. John on July 1, 2014 7:53 AM writes...

I used to use them very often and i did not have any corrosion problem. Room temperature in MeCN, overnight using normal borosilicate flask.

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3. Fluorine CHemist on July 1, 2014 8:53 AM writes...

I've used it many times, never noticed any corrosion, even did reactions in microwave above 120 °C, the vials weren't etched.What I can imagine is that in presence of strong acid SF can release HF.

Permalink to Comment

4. Coming to Light on July 1, 2014 9:26 AM writes...

I've set up my fair share of photochemical reactions using Selectfluor and I can tell you that it will eventually take its toll on laboratory glassware (we had to throw out microwave vials after a handful of uses as they became very cloudy)...for this reason we switched to Falcon culture tubes which, aside from not getting etched, were never reused. Our conditions were basic water or water/acetonitrile and irradiation at 300 nm.

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5. Anonymous on July 1, 2014 9:38 AM writes...

I've heated acetonitrile selectfluor mixtures at 60-80 degrees C and seen it cloud the glass. I was using borosilicate glass vials with vigorous stirring.

Permalink to Comment

6. Organometallica on July 1, 2014 11:07 AM writes...

Once upon a time in a former group, we had some stuff made by a grad student in the lab, and that stuff did all sort of work on glass/etc. Since recently getting a new batch from a group known in the department for having A++ stuff, I've seen no such problems. I chalk the etching up to some impurity that is either leftover or forms in impure material.

Permalink to Comment

7. Anion Effects on July 1, 2014 1:44 PM writes...

I think that some of the problem (for those who have experienced it) could come from hydrolysis of the BF4 counterion (a potential source of fluoride)...I wonder if people have had the same issue with anion swapped (eg PF6) variants.

Permalink to Comment

8. Anonymous on July 1, 2014 1:57 PM writes...

I work in a lab that has a very strong organofluorine focus, so we use it on a day to day basis, not uncommonly on a multigram scale.

I've not noticed any significantly rapid etching. Our glassware gets kind of cloudy slowly over time, but it's slow enough and not intense enough that it's not a problem, and it's definitely not assignable to selectfluor use.

People who rarely use it, does your glassware also slowly get cloudy over long periods of time?

Permalink to Comment

9. Ted on July 1, 2014 4:48 PM writes...

Hi:

We scaled a Deoxofluor process in acetonitrile and/or toluene a few years back. We ran at 60°C for >24h at one point, and etched a 20L Chemglass reactor.

Interestingly enough, the reactor glass was not cloudy or hazy - the etching was solely at the solvent level mark. You could feel it (a slightly depressed, 2cm wide band), but only a slight diffraction betrayed it visibly.

We didn't see this with any of our smaller scale reactions, but we also weren't looking for this (we were expecting haziness).

Beyond this scale we were in Hastelloy. Problem solved....

-t


Permalink to Comment

10. Anton on July 12, 2014 12:10 AM writes...

What kind of chemist are you again? Think back to sophomore organic and ask yourself what acid eats away at glass? Then ask yourself what type of side products or decomposition products could be in SelectFluor. You should be ashamed asking others to feed you the answer to this basic question. Shame on you (again)

Permalink to Comment

11. Anzo on July 24, 2014 10:40 PM writes...

Haters gonna hate

Permalink to Comment

12. Anonymous on December 18, 2014 4:50 PM writes...

Hey Anton, you are an ass. What is your degree in again? Why don't you tell us the mechanism of SF preparation and the mechanism by which HF is generated. Please also provide the exact conditions under which HF is generated and perhaps suggest which conditions might suppress HF generation. Just because something can happen doesn't mean it will (that even includes you knowing something).

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