Isaac was born on 5 September 1913 in Mile End Old Town, London to Nathaniel and Annie nee Oberlitski and he had three sisters, Leah, Clara and Marie. Their father Nathaniel worked as a greengrocer. In 1939 the family were living at 103 Claremont Road, West Ham where Isaac is listed as an account clerk for a grocery and provisions store. Isaac enlisted in 1941 and trained as a navigator.

Isaac was the navigator on Hudson T9333 which departed at 20.40 hours on 8 March 1942 on a night training exercise over the sea, from which the aircraft failed to return. Although an unknown aircraft was heard over the wireless telegraph, this was not however identified with T9333. Following post war enquiries and investigations, it was recorded in 1949 that the missing crew members had lost their lives at sea and are all commemorated on the Runnymede Memorial.

The crew members of T9333 were:
A/G, Phillip Crocker Bucknell, 4034410 RAAF
W/Op, A/G, Derek Maitland Hall, 403473 RAAF
Pilot, Thomas Colin Wills, 402898 RAAF
Nav, Isaac Sidney Woolf, 1375840