The applications of 2-hydroxy-β-nitrostyrenes as efficient bifunctional intermediates in organic synthesis are investigated in this review. For this purpose, reactions of 2-hydroxy-β-nitrostyrenes with diverse molecules, including carbonyl compounds, 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl compounds, hemiacetals, nitroalkenes, γ-butenolides, tetronic acid, azalactones, pyrazolones, enamines, malononitrile, methyleneindolinones, ylides, etc., were investigated to construct interesting biologically active scaffolds such as chromans, chromenes, coumarins, benzofurans and their fused and spiro rings, natural products, and other useful cyclic and acyclic compounds. The main focus is on the asymmetric synthesis of these compounds via cascade/domino/tandem reactions catalyzed by chiral organocatalysts. In this review, around 60 papers reported between the years 2000 and 2022 are presented.