r/OrganicChemistry

Benzene is classified as a carcinogen while chlorobenzene is not. Why do you think this is? As far as I understand it can participate in the same CYP450 mediated oxidation to form a (chloro)benzene oxide.

It makes sense to me why toluene would be less dangerous as other oxidation products (benzoic acid) can be formed but I dont see this as a possibility for chloro benzene.

Are there other factors in play? Is it because its potentiel carcinogenicity has not been investigated?

Would be happy to hear your thoughts (or the answer if you know)

I'm doing a university project where I have to use 2-pyridine carbaldehyde, however, we only had picolinic acid. Hence I thought about first reducing it to the alcohol and performing an oxidation to the aldehyde (i.e. lab didn't have DIBAL and I couldn't use LiAlH4 so I first made the picolinate ester and reduced with NaBH4 in MeOH/NaOMe). Now it's quite essential that we do not get substantial overoxidation to picolinic acid, as I have a limited amount of the alcohol but we may not use any of the chromium oxidants (PCC, PDC) and they are not a fan of DMP; cannot even use DCM or chloroform.

I actually considered this approach because we performed a similar pathway for oxidation of 4-methyl benzyl alcohol to the aldehyde using bleach in a biphasic reaction, but I feel quite stupid for not considering that the pyridine alcohol is quite soluble in water which was no problem with the benzyl alcohol. I thought I could just add a large amount of NaCl to saturation, but I have noticed that the pyride compounds really still tend to partition significantly in the waster layer and I cannot permit overoxidizing 50% of my alcohol, so I'm wondering whether you have suggestions.

It's quite strange in the sense that they have some quite exotic compounds; also we can work under nitrogen with ice bath, so this is all fine but they sometimes do not have standard compounds (today I had to make NaOMe myself) like MnO2, so any super niche reagents are not accessible.

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