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DCHAS-L Archives ยท Post dated February 27, 2018

Re: [DCHAS-L] safety of nucleophilic fluorination reagents

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Subject: Re: [DCHAS-L] safety of nucleophilic fluorination reagents

Date: Feb 27, 2018 15:08 UTC

Author: Margaret Rakas <mrakas**At_Symbol_Here**SMITH.EDU>

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From: Monona Rossol <0000030664c37427-dmarc-request**At_Symbol_Here**LISTS.PRINCETON.EDU>

Subject: Re: [DCHAS-L] safety of nucleophilic fluorination reagents

Date: Feb 27, 2018 17:14 UTC

Reply-To: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU>

In-Reply-To:  

Demystify: 

Sodium aluminum fluoride is called cyrolite by potters and is in a finely powdered (mostly respirable size) form in most glaze mixing rooms, sometimes in over 50 pound quantities or in open bins.  It is also an EPA-registered agricultural pesticide, so I'm often surprised at how casually it is used by potters. There are other fluoride-containing powdered materials, but this is the one I worry about most.  

Monona Rossol, M.S., M.F.A., Industrial Hygienist
President:  Arts, Crafts & Theater Safety, Inc.
Safety Officer: Local USA829, IATSE
181 Thompson St., #23
New York, NY 10012     212-777-0062
actsnyc**At_Symbol_Here**cs.com   www.artscraftstheatersafety.org

 


-----Original Message-----
From: Kristi Ohr <kohr**At_Symbol_Here**UMASS.EDU>
To: DCHAS-L <DCHAS-L**At_Symbol_Here**PRINCETON.EDU>
Sent: Tue, Feb 27, 2018 9:20 am
Subject: Re: [DCHAS-L] safety of nucleophilic fluorination reagents

Hi Tilak and all,
 
So I was thinking about it more from the standpoint of nucleophilic reagents generating fluoride anion and being in the lipophilic environment of the reaction or from having other organic materials present (including the cationic portion of the reagent itself).  I would think that those conditions would lead to the same deep tissue exposure potential of fluoride that makes HF so insidious.  Certainly under appropriate conditions these could generate HF, so there is that issue as well.  Electrophilic fluorination reagents would not pose the same threat because they would not generate fluoride anion.  The document from the Baran group below shows many different types of fluorination reagents, and is not specific to nucleophilic reagents.
 
Common examples of nucleophilic fluorination reagents include pyridine hydrofluoride, DAST, and even sodium or potassium fluoride in the presence of crown ethers to increase solubility and fluoride availability.
 
Just curious if anyone has developed programs for these, or knew of any exposures.
 
Thanks,
 
Kristi
 
From: ACS Division of Chemical Health and Safety [mailto:DCHAS-L**At_Symbol_Here**PRINCETON.EDU] On Behalf Of TILAK CHANDRA
Sent: Monday, February 26, 2018 8:02 PM
To: DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: Re: [DCHAS-L] safety of nucleophilic fluorination reagents
 
Hi Kristi:
 
There is a low probability of generating HF as a side product during nucleophilic fluorination. By the way which method researcher is using for forming the C-F bond? There are various methods available in the literature for such fluorination.
 

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