(E)-3-Iodoprop-2-enoic Acid, (Z)-Isomer

Abstract

(E)-3-Iodoprop-2-enoic acid [6372-02-7] C3H3O2I (MW 197.96) InChI = 1S/C3H3IO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1+ InChIKey = IBFDLVHJHUMSAC-OWOJBTEDSA-N (Z)-isomer [6214-35-3] C3H3O2I (MW 197.96) InChI = 1S/C3H3IO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1- InChIKey = IBFDLVHJHUMSAC-UPHRSURJSA-N (reagent used as a partner in metal-mediated coupling processes and esterification reactions, among others) Physical Data: (E)-isomer mp 146–149°C.1(Z)-isomer mp 62–64 °C.2 Solubility: soluble in most protic solvents, diethyl ether, and chloroform. Form Supplied in: (E)-isomer (not commercially available) and (Z)-isomer (commercially available) as a pale yellow to white crystalline solid. Analysis of Reagent Purity: (E)-isomer:1 1H NMR (400 MHz, CDCl3): δ = 11.7 (1H, br s), 8.07 (1H, d, J = 14.9), 6.90 (1H, d, J = 14.9); δC (100 MHz, CDCl3) 169.2, 135.7, 103.0. (Z)-isomer:3 1H NMR (270 MHz, CDCl3): δ = 9.94 (1H, br s), 7.69 (1H, d, J = 9.2), 6.99 (1H, d, J = 9.2); δC (67.8 MHz, CDCl3) 169.7, 129.4, 98.2. Preparative Methods: (E)-isomer: see Refs. 1 and 4. (Z)-isomer: see Ref 2 and 5-7. For references that give a selective method for the synthesis of both (E)- and (Z)-isomers, see Refs. 8-10. For synthesis of (Z)-ester analogues, see Refs 11-14. For synthesis of (Z)-amide and (Z)-nitrile analogs, see Refs 12 and 13. For synthesis of analogs substituted on the alkene terminus, see Ref. 15. Purification: (E)-isomer can be obtained by fractional crystallization using petroleum ether (40–60): diethyl ether.8-15 (Z)-isomer can be recrystallized from hexane,6, 9 petroleum ether (40-60): diethyl ether,2, 8 or dichloromethane:hexane.9 In some procedures, the (E)- or (Z)-isomer products precipitate out of the reaction mixture directly and can be isolated by straightforward filtration and washing with hexanes3 or water.1 Handling, Storage, and Precautions: both (E)- and (Z)-isomers require the same precautionary measures. They are lachrymators and can cause burns. They should be stored in tightly closed containers in a refrigerator at or below 4 °C, in a dry area. Although not listed as carcinogens, their toxicological properties have not yet been fully investigated. They are incompatible with strong oxidizing agents and strong bases.