First appearance of the Scarecrow in the Iron Man story, "The Sinister Scarecrow!"
Script by Stan Lee
Art by Don Heck

A contortionist becomes the Scarecrow and steals some plans from Tony Stark to sell them to Cuba. Iron Man follows the Scarecrow and steals back the plans.

Iron Man [Tony Stark], Scarecrow [Ebenezer Laughton, stage name "Uncanny Umberto"] (introduction, origin), Pepper Potts, Happy Hogan, Veronica Vogue

for sale