Talk:Fluoroaspirin

Article title[edit]

I'm curious whether fluoroaspirin is truly the common name for this chemical. Aspirin itself is a genericized trademark in the United States but an active trademark in much of the world, and as far as I know is almost always used when considering the substance as a medication rather than as a chemical. This fluorinated substance on the other hand does not seem to have any medical use.

I wonder if it would be better to move the article to fluoroacetylsalicylic acid or some such. Could some chemist with knowledge in the area be moved to comment? --Trovatore (talk) 18:52, 29 November 2022 (UTC)[reply]

Rename. Although "fluoroaspirin" seems to be a name used in the literature for this chemical, the name is structurally ambiguous. Other isomers also exist and are also of literature interest, with the fluorine on any of several different positions around the benzene ring rather than on the acyl-methyl. Therefore, I think a more-systematic name would be better. ~~Trovatore's specific proposal is a good one.~~ DMacks (talk) 20:06, 29 November 2022 (UTC)[reply]
Comment: Fluoroacetylsalicylic acid would be just as ambiguous as fluoroaspirin, as the fluoro group could still be on the ring rather then part of the acetyl group. I think the cleanest, structurally unambiguous name would be 2-(fluoroacetyl)salicylic acid. That said, enwiki has many cases where compound names that could refer to multiple isomers are used as an article title for a specific isomer if 1) that isomer is by far the most notable, and 2) enwiki only has an article on that isomer and not any others that would require disambiguation. So I think any of these titles would be fine, especially for a relatively obscure compound. Mdewman6 (talk) 21:30, 29 November 2022 (UTC)[reply]
Good point. I mentally parsed it as "(fluoroacetyl)salicylic acid". For the record, 3-fluoroaspirin, 4-fluoroaspirin, 5-fluoroaspirin, and 6-fluoroaspirin are all known, as well as everal other-halogen variants, though I'd be hard-pressed to call any of them "notable" each in their own right. DMacks (talk) 22:08, 29 November 2022 (UTC)[reply]
I wasn't thinking much about ambiguity; I was just wondering if the name is really the most standard one among those who study this substance. Maybe that's such a niche area that the question doesn't mean much. But I just had an intuition that it was an odd mixture of registers, adding the fluoro- to a common name coming from pharmaceutics rather than chemistry. --Trovatore (talk) 04:58, 30 November 2022 (UTC)[reply]
Rename. Calling it fluoroaspirin encouages readers to suppose it might be some sort of super-aspirin. It isn't. It has according to Pubchem a mouse LD₅₀ of 15 mg/kg, which is not surprising since it will readily metabolise into fluoroacetic acid, a well-known toxin (sodium fluoroacetate is even used as a rodenticide). Personally, I would delete the article as being for a non-notable chemical but if it is to stay it should be given the correct chemical name of 2-(2-Fluoroacetoxy)benzoic acid, or a synonym like 2-(fluoroacetyl)salicylic acid. Mike Turnbull (talk) 11:17, 30 November 2022 (UTC)[reply]