1,3‐Dichloro‐2‐butene

(1) (E/Z) (X = Cl, Y = Cl) [926-57-8] C4H6Cl2 (MW 125.00) InChI = 1S/C4H6Cl2/c1-4(6)2-3-5/h2H,3H2,1H3 InChIKey = WLIADPFXSACYLS-UHFFFAOYSA-N (E)-(1) (X = Cl, Y = Cl) [7415-31-8] (Z)-(1) (X = Cl, Y = Cl) [10075-38-4] InChI = 1S/C4H6Cl2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2- InChIKey = WLIADPFXSACYLS-RQOWECAXSA-N InChI = 1S/C4H6Cl2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2- InChIKey = WLIADPFXSACYLS-RQOWECAXSA-N (2) (E/Z) (X = Cl, Y = Br) [51430-83-2] C4H6BrCl (MW 169.45) InChI = 1S/C4H6BrCl/c1-4(6)2-3-5/h2H,3H2,1H3 InChIKey = FMVAGJFXZXHXHY-UHFFFAOYSA-N (3) (E/Z) (X = Cl, Y = I) [54201-06-8] C4H6ClI (MW 216.45) InChI = 1S/C4H6ClI/c1-4(5)2-3-6/h2H,3H2,1H3 InChIKey = XIGISXDJPIFSMC-UHFFFAOYSA-N (E)-(4) (X = Br, Y = Br) [86365-83-5] C4H6Br2 (MW 213.90) InChI = 1S/C4H6Br2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2+ InChIKey = CXCKBPHWDONPBF-DUXPYHPUSA-N (Z)-(4) (X = Br, Y = Br) [86365-84-6] (E)-(5) (X = I, Y = Cl) [135663-74-0] C4H6ClI (MW 216.45) InChI = 1S/C4H6Br2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2- InChIKey = CXCKBPHWDONPBF-RQOWECAXSA-N InChI = 1S/C4H6ClI/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2+ InChIKey = JROJXAHKIDDWSW-DUXPYHPUSA-N (Z)-(5) (X = I, Y = Cl) [138174-48-8] (Z)-(6) (X = I, Y = I) [134005-20-2] C4H6I2 (MW 307.90) InChI = 1S/C4H6ClI/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2- InChIKey = JROJXAHKIDDWSW-RQOWECAXSA-N InChI = 1S/C4H6I2/c1-4(6)2-3-5/h2H,3H2,1H3/b4-2- InChIKey = MTIFMNTZMLZREE-RQOWECAXSA-N (aldol, alkenyl radical, organopalladium/Heck annulations; methyl ketone precursor; alkyne precursor; alkenyl organometallic precursor; allylic nucleophile precursor) Alternate Name: Wichterle reagent (1). Physical Data: (E)-(1) bp 40 °C/20 mmHg; (Z)-(1) bp 35 °C/20 mmHg; (Z)-(4) bp 66 °C/13 mmHg. Preparative Methods: see appropriate reference: (1),2a,3 (2),7a (3),12a (4),14b,15d,e (5),15c,f (6).15a Handling, Storage, and Precautions: reagent (1) shows an acute LD50 (inhalation, 4 h) of 546 ppm in rats.2a Acute and chronic toxicity to the kidney and other major organs is well established.2 As low molecular weight allylic halides, these reagents can be expected to be lachrymatory, irritating to and absorbed through the skin and mucous membranes, especially hazardous via inhalation, and suspect carcinogens. The usual stability order I < Br < Cl applies for both X and Y. The iodoallyl reagent (3) is photolabile;12a the iodoalkenyl reagent (Z)-(5) is reported to decompose above 25 °C.15f