Old English fif "five," from Proto-Germanic *fimfe (source also of Old Frisian fif, Old Saxon fif, Dutch vijf, Old Norse fimm, Old High German funf, Gothic fimf), from PIE root *penkwe- "five." The lost *-m- is a regular development (compare tooth).
Five-and-ten (Cent Store) is from 1880, American English, with reference to prices of goods for sale. Five-star (adj.) is from 1913 of hotels, 1945 of generals. Slang five-finger discount "theft" is from 1966. The original five-year plan was 1928 in the U.S.S.R. Five o'clock shadow attested by 1937.
[under picture of a pretty girl] "If I were a man I'd pay attention to that phrase '5 O'Clock Shadow.' It's that messy beard growth which appears prematurely about 5 P.M." [Advertisement for Gem razors and blades, Life," May 9, 1938]