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Check outbound email TO field for domain

Hi All,
We have a request dealing with the email object in Salesforce.
The request is to alert a user sending an email from a case that they are about to send to an external email address (not our domain). Sometimes our employees and clients have the same or similar names and every so often an incorrect TO: is picked. 
Google hasn't kicked out any results around this and I was wondering if anyone has dealt with this before and if so how.