A D&D group is just like any other social group in that it has (usually unspoken) norms of behaviour. These norms are circumstantial and may be subject to external constraints: for example, the way you behave with your friendship group is different in church from at a football match (external constraint) and different from when you gather to watch a movie or play D&D (circumstantial).
When someone breaches these norms they make us uncomfortable, upset or even angry depending on the egregiousness of the breach and the frequency of such breaches. A friend talking during the movie once is different to talking repeatedly and different from that same person throwing a punch.
The point here is that "inappropriate" is contextual - a joke that is inappropriate to tell in front of your mother might be quite suitable to tell at an open-mike night at a comedy club.
What are your norms?
It is unclear from your question if the behaviors you are talking about (except for the interruptions and probably the one about going to brothels) are happening within the role-playing or outside the role-playing.
These are different contexts and, as stated above, different norms may apply - some groups like exploring dark issues of questionable morality within the role-play and, alternatively, some groups expect that the social norms that apply to the players will also apply to the characters. Because these norms are often unspoken, some parts of the group may not be on the same page about them.
This is a group decision - its not yours alone, however, as DM you clearly have a lot of influence.
So, if your group is comfortable with him playing a sleazeball, misogynistic, sexual harasser who insults his friends, frequents brothels and misses appointments in the game then that's fine. Of course, its also perfectly fine that the game world will react to such a character appropriately: that is, in-game actions have in-game consequences.
What is not fine is:
- him doing that if its not acceptable to the group,
- him using that as a cover to be a sleazeball, misogynistic, sexual harasser who insults his friends, frequents brothels and misses appointments in real life,
- him actually being a sleazeball, misogynistic, sexual harasser who insults his friends, frequents brothels and misses appointments.
If any of these things are happening then you need to consider if you want this person as a friend: that is, out-of-game actions have out-of-game consequences.
This is in a different type of inappropriate behaviour and is entirely concerned with the player not the character.
To be honest, I'm struggling to see how a strict "hand-raising rule" would actually work but if that's what your group wants then all power to you.
The breach of this "social norm" is clearly not as egregious as the other but it will be annoying if it is persistent. Approach it with more tolerance.
- Establish your social norms - including appropriate sanctions for breaching them
- Enforce these.