[diazepamx]

Hello,

Forgive me I am a junior chemist. I am concerned because I used about 1 ml of MOMCl in a reaction involving a phenol substrate and DIPEA and DCM as solvent. Rather than working it up (following rxn) and diluting it beforehand, I concentrated the mixture using the rotovap and felt like I most likely inhaled whatever ether may have evaporated out. Our rotovap is not placed in a fume hood.
Has anybody experienced anything similar? Wondering what my chances of getting sick are?

Thank you.

[pgk]

Chloromethyl methyl ether is carcinogen but after a repeated and relatively chronic exposure. So, don’t worry if its inhalation has happened only one time.
But for your safety in the future, you must follow the rules that are listed below:
1). Inform yourself about the health risks of all the reagents you use and what to do if something wrong happen.
2). Chemical reactions must be effectuated in the fume hood.
3). Take the appropriate safety measures, wear protection glass and wear a gas mask during working with dangerous and volatile chemicals.
4). You work up by following the exact operational procedure that is described in the reference source without changing working parameters and conditions.
5). Do not smoke and do not eat or drink in a chemical lab, during a break.
6). After ending your lab work, you have to clean carefully all used glassware and your hands.

[rolnor]

Is it not the impurity bis-chloromethyl ether that is responsible fot the carcinogenic properties? I think that
bromomethyl methyl ether is at least not on any list of carcinogenics and is a good substitute. If you add a little ammonia when working up you will destroy any remaining reagent.

[pgk]

The carcinogenic properties of these substances, is supposed to be due to the formation of oxonium salts (at extremely low ratio), which are strong alkylating agents.
CH3OCH2Cl → CH3O(+)=CH2,Cl(-)
Therefore, all compounds with similar structure must be considered as carcinogenic. Besides, there is no official obligation of special labeling, if the compound’s carcinogenicity is classified in group 3 or 4 (= no proven carcinogenicity in humans and animals).
http://monographs.iarc.fr/ENG/Classification/

[rolnor]

Here is a link
https://en.m.wikipedia.org/wiki/Chloromethyl_methyl_ether
And
https://en.m.wikipedia.org/wiki/Bis(chloromethyl)_ether

The chloromethyl methyl ether is carcinogenic in itself but they also mention the bis chloromethyl ether as a impurity and this is formed in an older synthesis method. The bis chloromethyl ether is much more dangerous.
In any case the work-up I suggest with little ammonia would destroy any remaining chloro-ether.

[pgk]

As a result of its alkylating properties, the bis-chloromethyl ether additionally behaves as cross linker to proteins and nucleic acids and therefore, it is more dangerous.