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2-Butynoic acid is used as an intermediate in organic synthesis and pharmaceuticals. It is used as a synthon in various reactions, which includes cylcoalkylation of phenols to flavones and chromones. It is involved in the cyclization of gamma-butyrolactones. It is also used in the synthesis of Z-trisubstituted olefins through µ-alkylation. It plays an important role in the preparation of chirally pure 1,2,3,4-tetrahydroisoquinoline analogs, which finds application as anti-cancer agents.
For Diels-Alder reactions with dienes, see: Chem. Ber., 114, 1793 (1981); Liebigs Ann. Chem., 1089 (1981).
The dilithio derivative can be alkylated at the 4-position. The resulting Li salts can, if required, be converted directly to their TMS or methyl esters by reaction with TMS chloride or MeI: Tetrahedron Lett., 83 (1979).
Yan, H.; Mao, J.; Rong, G.; Liu, D.; Zheng, Y.; He, Y. Facile synthesis of (E)-beta-nitroolefinic alkoxyamines via silver-catalyzed decarboxylative nitroaminoxylation of phenylpropiolic acids. Green Chem. 2015, 17 (5), 2723-2726.
Zheng, Y.; Mao, J.; Rong, G.; Xu, X. A NCS mediated oxidative C-H bond functionalization: direct esterification between a C(sp3)-H bond and carboxylic acids. Chem. Commun. 2015, 51 (42), 8837-8840.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P280-P305+P351+P338-P308+P313
Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention.