a lot of files do not have a content type, if they did, don't you think Microsoft would provide a ContentType property for FileInfo class? that said, here is something you might want to look into:
HOW TO: work with the Windows Registry to determine the content-type of a file based on the file extension
http://www.aspemporium.com/aspEmporium/cshrp/howtos/howto.asp?hid=19