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We have our application hosted on Windows Server 2012 and IIS 7.5 but the application crashed when it's application pool went above 4.5 GB with just few users. This is the error stack in Windows Event viewer:

Description: The process was terminated due to an unhandled exception.
Exception Info: System.OutOfMemoryException
Stack:
   at System.Collections.ArrayList..ctor(Int32)
   at System.Web.RequestTimeoutManager.CancelTimedOutRequests(System.DateTime)
   at System.Web.RequestTimeoutManager.TimerCompletionCallback(System.Object)
   at System.Threading.ExecutionContext.RunInternal(System.Threading.ExecutionContext, System.Threading.ContextCallback, System.Object, Boolean)
   at System.Threading.ExecutionContext.Run(System.Threading.ExecutionContext, System.Threading.ContextCallback, System.Object, Boolean)
   at System.Threading.TimerQueueTimer.CallCallback()
   at System.Threading.TimerQueueTimer.Fire()
   at System.Threading.QueueUserWorkItemCallback.System.Threading.IThreadPoolWorkItem.ExecuteWorkItem()
   at System.Threading.ThreadPoolWorkQueue.Dispatch()

What is the best way to find out the offending piece? How can we monitor the application and what is happening which causes the pool to crash?

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