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Question: constantly listening to music.

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Hello everyone.
I like to go to sleep with music in the background and usually I listen to it from my PC (conected to a Sony system). I had an idea: To listen to music from my iphone in one of the two ways:

1. Plugging it straight to the system with like an "audio in/aux" cable. Problem is: Otterbox case, My cable is too thick to get in it...

2. Plugging the cable to this device I have that connects to the iPhone using Bluetooth, and then "delivers the music to earphones or the system in this case.
[The device is something like this.. Just without the earphones in this case...
]

And here is my question. Is it okay to listen to music for like 8-10-even 12 hours? Isn't it bad for the iPhone?

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