Derek Lowe's commentary on drug discovery and the pharma industry. An editorially independent blog from the publishers of Science Translational Medicine. All content is Derek’s own, and he does not in any way speak for his employer.
Well, it’s been a bit too serious around here this week. So I thought today I’d step back to a period when men were men and chlorine azide was a reactive, toxic, and unstable compound that was only good for finding out what sort of explosion it would set off next. What’s that? You say… Read More
Tetrazole derivatives have featured several times here in “Things I Won’t Work With”, which might give you the impression that they’re invariably explosive. Not so – most of them are perfectly reasonable things. A tetrazole-for-carboxyl switch is one of the standard med-chem tricks, standard enough to have appeared in… Read More
That would be my reaction if asked to take a look at the structures in this new paper in JACS. As the authors, who tiptoe gingerly every morning into the State Key Laboratory of Explosion Science and Technology in Beijing put it: “The larger the number of directly linked nitrogen atoms, the more difficult the… Read More
For once, I’m going to farm out a “Things I Won’t Work With” post to someone else. For those who missed it in the comments, here’s the link to the PDF of Max Gergel’s extraordinary memoir “Excuse Me Sir, Would You Like to Buy a Kilo of Isopropyl Bromide?” Gergel founded Columbia Organic Chemicals, and… Read More
Everyone’s heard of cyanide, whether they’ve spent any time in a chemistry classroom or not. And if you form a covalent bond to the carbon of that CN group, you’ve got a nitrile, and those are familiar compounds to any organic chemist. But what if you flip the group around and bond it via the… Read More
The latest addition to the long list of chemicals that I never hope to encounter takes us back to the wonderful world of fluorine chemistry. I’m always struck by how much work has taken place in that field, how long ago some of it was first done, and how many violently hideous compounds have been… Read More
Organometallic reagentss come from large tribes, and there are always wild cousins up in the hills. A good place to look for the livelier ones is in the simplest alkyl derivatives, and you should go all the way down to the methyls if you want to know their real character. Ignore the halides. Methylmagnesium bromide… Read More
My recent entries in this category have, for the most part, been hazardous in a direct (not to say crude, or even vulgar) manner. These are compounds that explode with bizarre violence even in laughably small amounts, leaving ruined equipment and shattered nerves in their wake. No, I will not work with such. But today’s… Read More
The Klapötke group at Munich are some of the masters of alarming chemical structures, and they basically seem to own the field of chalcogen azides. Perhaps the competition for this class of compounds is not as intense as it might be – the other labs doing this sort of thing are collaborations between USC and… Read More
An early favorite has appeared in my “most alarming chemical papers” file for this year. Thomas Klapoetke and Joerg Stierstorfer from Munich have published one with a simple title that might not sound unusual to people outside the field, but has made every chemist I’ve shown it to point like a bird dog: “The CN7… Read More
