The most likely paraphrase of simple past:
When did your brother contact you?
is, On what occasion or at what time did your brother contact you?
An answer might be:
My brother contacted me when the plane landed.
The answer refers to a single event that happened in the past.
The most likely paraphrase of the present perfect:
When has your brother contacted you?
is, On what occasions or under what circumstances did your brother contact you?
An answer might be:
My brother contacted me whenever he was feeling homesick.
My brother has contacted me whenever he is feeling homesick.
The present perfect will NOT refer to a single incident that took place entirely in the past and does not impinge on the present.