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.

http://www.scripps.edu/baran/images/grpmtgpdf/Su_May_08.pdf

Good luck.

Tilak

---

From: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU> on behalf of Kristi Ohr <kohr**At_Symbol_Here**UMASS.EDU>
Sent: Monday, February 26, 2018 5:06:04 PM
To: DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: [DCHAS-L] safety of nucleophilic fluorination reagents

Is anyone else treating nucleophilic fluorination reagents in the same way as HF in terms of precautions and emergency response? I'm not finding any data on the subject aside from recommendations to have calcium gluconate on hand in SDSs.

Thanks,

Kristi

Kristi Ohr, Ph.D.
Chemical Safety Services Manager

Environmental Health and Safety
UMass Amherst
40 Campus Center Way
Draper Hall
Amherst, MA 01003
Office: 413-545-5117

Cell: 413-800-4408

kohr**At_Symbol_Here**ehs.umass.edu

www.ehs.umass.edu

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