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1403:
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922:
1074:. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. Acetylacetone is a building block for the synthesis of many
690:
647:
938:
2027:
Smith, Kyle T.; Young, Sherri C.; DeBlasio, James W.; Hamann, Christian S. (12 April 2016). "Measuring
Structural and Electronic Effects on Keto–Enol Equilibrium in 1,3-Dicarbonyl Compounds".
836:
2095:
Manbeck, Kimberly A.; Boaz, Nicholas C.; Bair, Nathaniel C.; Sanders, Allix M. S.; Marsh, Anderson L. (2011). "Substituent
Effects on Keto–Enol Equilibria Using NMR Spectroscopy".
64:
54:
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94:
84:
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is equal or greater than 1, the enol form is favoured. The keto form becomes more favourable in polar, hydrogen-bonding solvents, such as water. The enol form is a
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202:
832:
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2319:
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820:
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Yoshida, Z.; Ogoshi, H.; Tokumitsu, T. (1970). "Intramolecular hydrogen bond in enol form of 3-substituted-2,4-pentanedione".
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2011:
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Acetylacetone is a versatile bifunctional precursor to heterocycles because both keto groups may undergo
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2134:
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Because of the ease of these syntheses, many analogues of acetylacetonates are known. Some examples are
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A comprehensive database of published data on equilibrium constants of metal complexes and ligands
1208:, meaning the hydrogen atom is shared equally between the two oxygen atoms. In the gas phase, the
772:
3111:
2233:
2206:
1836:. A general method of synthesis is to treat a metal salt with acetylacetone in the presence of a
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2379:
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2007:
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2211:"Critical evaluation of equilibrium constants involving acetylacetone and its metal chelates"
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Both oxygen atoms bind to the metal to form a six-membered chelate ring. In some cases the
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values for this equilibrium in aqueous solution at 25 °C are 8.99 ± 0.04 (
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165:
2110:
1187:
876:
452:
301:
239:
3131:
2374:
2345:
1871:
1800:, wherein the oxygen atoms in acetylacetone are replaced by NR (R = aryl, alkyl).
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1509:
993:
756:
1402:
3105:
2147:
1944:
1887:
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1517:
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1219:, is 11.7, favoring the enol form. The two tautomeric forms can be distinguished by
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373:
808:
17:
2185:
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bonds are equivalent. Both C-C central bonds are equivalent as well, with one
1238:
768:
566:
270:
2344:
Straganz, G.D.; Glieder, A.; Brecker, L.; Ribbons, D.W.; Steiner, W. (2003).
2304:
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2003:
2289:
Denoon, C. E. Jr.; Adkins, Homer; Rainey, James L. (1940). "Acetylacetone".
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as well. Acetylacetone degradation has been characterized in the bacterium
710:
2346:"Acetylacetone-cleaving enzyme Dke1: a novel C–C-bond-cleaving enzyme from
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cleaves the carbon-carbon bond of acetylacetone, producing acetate and
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1544:
Acetylacetone is prepared industrially by the thermal rearrangement of
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A second synthesis involves the base-catalyzed condensation (e.g., by
1922:
1797:
1529:
1454:
1443:
1419:
1415:
1230:
The equilibrium constant tends to be high in nonpolar solvents; when
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250:
992:
Except where otherwise noted, data are given for materials in their
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1401:
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acetylacetone twice. The resulting dilithium species can then be
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is so strong that no added base is needed to form the complex.
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1111:
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436:
93:
83:
63:
53:
1201:
of acetylacetone coexist in solution. The enol form has C
915:
2251:
Siegel, Hardo; Eggersdorfer, Manfred (2002). "Ketones".
1512:). Values for mixed solvents are available. Very strong
1010:
1996:
e-EROS Encyclopedia of
Reagents for Organic Synthesis
1796:. Condensation with two aryl- or alkylamines gives
1558:Laboratory routes to acetylacetone also begin with
1430:). Those two equivalencies are because there is a
2163:Solvents and Solvent Effects in Organic Chemistry
372:
919:
164:
2254:Ullmann's Encyclopedia of Industrial Chemistry
1894:-dependent, but it has been proven to bind to
2421:
1994:Thomas M. Harris (2001). "2,4-Pentanedione".
8:
1426:atom bonded to the central carbon atom (the
1406:The structure of the acetylacetonate anion (
27:"Acac" redirects here. For other uses, see
2428:
2414:
2406:
2054:Caminati, W.; Grabow, J.-U. (2006). "The C
451:
300:
278:
33:
2373:
2284:
2282:
476:InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
408:
68:Ball-and-stick model of the keto tautomer
58:Ball-and-stick model of the enol tautomer
2061:Journal of the American Chemical Society
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1438:in the acetylacetonate anion, where the
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486:InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
98:Space-filling model of the keto tautomer
88:Space-filling model of the enol tautomer
2401:International Chemical Safety Card 0533
1968:
1442:of those four bonds is about 1.5. Both
507:
472:
447:
2457:
976:340 °C (644 °F; 613 K)
612:140 °C (284 °F; 413 K)
291:
2920:
1832:, Na(acac), is the precursor to many
602:−23 °C (−9 °F; 250 K)
479:Key: YRKCREAYFQTBPV-UHFFFAOYSA-N
258:
238:
7:
2447:
2058:Structure of Enolic Acetylacetone".
1749:2,2,6,6-tetramethyl-3,5-heptanedione
962:34 °C (93 °F; 307 K)
1759:are also used to generate volatile
1645:, followed by acidification of the
1477: = 0), 8.83 ± 0.02 (
1414:In the acetylacetonate anion, both
489:Key: YRKCREAYFQTBPV-UHFFFAOYAO
363:
347:
1060:. It exists in equilibrium with a
25:
1780:. For example, condensation with
1450:. The acetylacetonate anion is a
1551:
1000:
680:
675:
670:
665:
550:
40:
1334:. It forms the acetylacetonate
996:(at 25 °C , 100 kPa).
1434:between the four bonds in the
556:
544:
118:(3Z)-4-Hydroxy-3-penten-2-one
1:
2161:Reichardt, Christian (2003).
2098:Journal of Chemical Education
2029:Journal of Chemical Education
1493:) and 9.00 ± 0.03 (
2333:. Gustavus Adolphus College.
2148:10.1016/0040-4020(70)80005-9
1056:. It is classified as a 1,3-
2165:(3rd ed.). Wiley-VCH.
2041:10.1021/acs.jchemed.5b00170
79:
49:
3148:
2922:
2218:Pure and Applied Chemistry
1807:
1041:with the chemical formula
26:
2459:
2444:
1884:acetylacetone dioxygenase
1834:acetylacetonate complexes
1757:hexafluoroacetylacetonate
990:
646:
641:
531:
498:
463:
148:
131:
113:
108:
78:
48:
39:
2305:10.15227/orgsyn.020.0006
2263:10.1002/14356007.a15_077
2004:10.1002/047084289X.rp030
1788:while condensation with
1446:atoms equally share the
751:Precautionary statements
2348:Acinetobacter johnsonii
2257:. Weinheim: Wiley-VCH.
2230:10.1351/pac198254122557
1901:Acinetobacter johnsonii
1578:) upon the addition of
631:Magnetic susceptibility
1977:"05581: Acetylacetone"
1830:Sodium acetylacetonate
1826:
1810:Metal acetylacetonates
1804:Coordination chemistry
1753:Trifluoroacetylacetone
1647:sodium acetylacetonate
1411:
1357:(commonly abbreviated
1191:
1080:heterocyclic compounds
1076:coordination complexes
926:
99:
89:
69:
59:
2437:Metal acetylacetonate
1817:
1405:
1190:
925:
97:
87:
67:
57:
29:ACAC (disambiguation)
1820:ball-and-stick model
1436:O-C2-C3-C4-O linkage
1249:Acid–base properties
1210:equilibrium constant
908:(fire diamond)
523:: CC(O)=CC(=O)C
2354:Biochemical Journal
2111:2011JChEd..88.1444M
1546:isopropenyl acetate
1497: = 1.0 M
1330:Acetylacetone is a
1227:and other methods.
1069:−C(=O)−CH=C(−OH)−CH
619:Solubility in water
574: g·mol
220:Beilstein Reference
36:
3127:3-Hydroxypropenals
2366:10.1042/BJ20021047
2191:2017-06-19 at the
1827:
1412:
1192:
1023:Infobox references
927:
123:Pentane-2,4-dione
100:
90:
70:
60:
34:
3099:
3098:
3093:
3092:
2292:Organic Syntheses
2224:(12): 2557–2592.
2186:IUPAC SC-Database
2142:(24): 5691–5697.
2119:10.1021/ed1010932
2105:(10): 1444–1445.
2074:10.1021/ja055333g
1855:Hacac ⇌ M(acac)
1651:hydrogen chloride
1641:) of acetone and
1580:boron trifluoride
1481: = 0.1
1328:
1327:
1185:
1184:
1031:Chemical compound
1029:
1028:
705:Hazard statements
637:−54.88·10 cm/mol
582:Colorless liquid
432:CompTox Dashboard
208:Interactive image
197:Interactive image
190:Interactive image
104:
103:
74:
73:
18:Pentane-2,4-dione
16:(Redirected from
3139:
3117:Chelating agents
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2423:
2416:
2407:
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2318:O'Brien, Brian.
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2207:Liljenzin, J. O.
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2017:
1991:
1985:
1984:
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1958:
1890:. The enzyme is
1866:
1738:dibenzoylmethane
1728:
1703:
1640:
1622:
1588:
1577:
1564:acetic anhydride
1555:
1520:compounds, will
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1409:
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1355:
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1253:
1221:NMR spectroscopy
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1095:
1073:
1055:
1039:organic compound
1013:
1007:
1004:
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982:Explosive limits
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940:
933:
918:
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539:Chemical formula
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329:Gmelin Reference
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140:2,4-Pentanedione
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2396:
2395:External links
2393:
2390:
2389:
2360:(3): 573–581.
2336:
2325:
2324:& Co(acac)
2321:
2310:
2278:
2271:
2243:
2197:
2178:
2171:
2153:
2124:
2087:
2068:(3): 854–857.
2055:
2046:
2035:(4): 790–794.
2019:
2012:
1986:
1967:
1966:
1964:
1961:
1960:
1959:
1879:
1878:Biodegradation
1876:
1872:chelate effect
1868:
1867:
1823:
1808:Main article:
1805:
1802:
1773:
1770:
1768:
1765:
1734:benzoylacetone
1730:
1729:
1704:
1624:
1623:
1562:. Acetone and
1541:
1538:
1510:Ionic strength
1469:
1400:
1399:
1326:
1325:
1322:
1319:
1315:
1314:
1311:
1308:
1300:
1299:
1296:
1293:
1285:
1284:
1281:
1278:
1270:
1269:
1266:
1260:
1257:
1250:
1247:
1241:analogue of a
1234:
1216:
1202:
1183:
1182:
1179:
1173:
1172:
1169:
1163:
1162:
1159:
1148:
1147:
1144:
1138:
1137:
1134:
1128:
1127:
1124:
1118:
1117:
1114:
1108:
1107:
1104:
1099:
1092:
1089:
1087:
1084:
1030:
1027:
1026:
1021:
999:
998:
994:standard state
991:
988:
987:
984:
978:
977:
974:
967:
964:
963:
960:
954:
953:
943:
936:
929:
914:
913:
912:
911:
909:
900:
899:
837:P305+P351+P338
829:P303+P361+P353
754:
749:
746:
745:
708:
703:
700:
699:
694:
689:
686:
685:
663:
658:
655:
654:
644:
643:
639:
638:
635:
629:
626:
625:
624:16 g/(100 mL)
622:
617:
614:
613:
610:
604:
603:
600:
594:
593:
590:
584:
583:
580:
576:
575:
569:
563:
562:
559:
553:
547:
542:
537:
534:
533:
529:
528:
526:
525:
519:
517:
514:
512:
509:
501:
500:
499:
496:
495:
493:
492:
488:
485:
484:
482:
478:
475:
474:
466:
465:
464:
461:
460:
458:
457:
444:
442:
430:
427:
426:
423:
417:
416:
414:
413:
405:
403:
397:
396:
394:
393:
389:
387:
381:
380:
378:
377:
369:
367:
359:
356:
355:
353:
352:
344:
342:
336:
335:
332:
327:
324:
323:
321:
320:
316:
314:
306:
305:
295:
287:
286:
284:
283:
275:
273:
267:
266:
264:
263:
255:
253:
247:
246:
244:
243:
235:
233:
227:
226:
223:
218:
215:
214:
212:
211:
200:
193:
185:
183:
176:
173:
172:
170:
169:
161:
159:
154:
151:
150:
146:
145:
142:
141:
138:
134:
133:
129:
128:
117:
111:
110:
106:
105:
102:
101:
91:
76:
75:
72:
71:
61:
46:
45:
35:Acetylacetone
24:
14:
13:
10:
9:
6:
4:
3:
2:
3144:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3109:
3107:
3088:
3085:
3082:
3079:
3076:
3073:
3070:
3067:
3064:
3061:
3058:
3055:
3052:
3049:
3046:
3045:
3042:
3036:
3034:
3028:
3026:
3020:
3018:
3012:
3010:
3004:
3002:
2996:
2994:
2988:
2986:
2979:
2973:
2971:
2965:
2962:
2960:
2954:
2952:
2946:
2944:
2938:
2936:
2930:
2927:
2926:
2919:
2915:
2912:
2909:
2906:
2903:
2900:
2897:
2894:
2891:
2888:
2885:
2882:
2879:
2876:
2873:
2870:
2867:
2864:
2861:
2860:
2856:
2853:
2850:
2847:
2844:
2842:
2839:
2836:
2833:
2831:
2825:
2823:
2817:
2814:
2811:
2808:
2805:
2803:
2797:
2795:
2789:
2786:
2784:
2778:
2775:
2774:
2770:
2767:
2764:
2761:
2758:
2756:
2750:
2747:
2744:
2742:
2736:
2734:
2727:
2721:
2719:
2713:
2710:
2708:
2698:
2695:
2693:
2687:
2685:
2679:
2677:
2674:
2671:
2670:
2666:
2663:
2660:
2657:
2654:
2652:
2646:
2644:
2638:
2636:
2630:
2628:
2623:
2621:
2614:
2608:
2606:
2599:
2593:
2590:
2588:
2581:
2575:
2573:
2566:
2560:
2558:
2551:
2541:
2539:
2533:
2531:
2528:
2525:
2524:
2520:
2517:
2514:
2511:
2508:
2506:
2500:
2497:
2495:
2492:
2491:
2487:
2484:
2481:
2478:
2475:
2472:
2469:
2466:
2465:
2461:
2455:
2453:
2450:
2449:
2443:
2438:
2431:
2426:
2424:
2419:
2417:
2412:
2411:
2408:
2402:
2399:
2398:
2394:
2385:
2381:
2376:
2371:
2367:
2363:
2359:
2355:
2351:
2349:
2340:
2337:
2329:
2314:
2311:
2306:
2302:
2298:
2294:
2293:
2285:
2283:
2279:
2274:
2272:9783527306732
2268:
2264:
2260:
2256:
2255:
2247:
2244:
2239:
2235:
2231:
2227:
2223:
2219:
2212:
2208:
2201:
2198:
2194:
2190:
2187:
2182:
2179:
2174:
2172:3-527-30618-8
2168:
2164:
2157:
2154:
2149:
2145:
2141:
2137:
2136:
2128:
2125:
2120:
2116:
2112:
2108:
2104:
2100:
2099:
2091:
2088:
2083:
2079:
2075:
2071:
2067:
2063:
2062:
2050:
2047:
2042:
2038:
2034:
2030:
2023:
2020:
2015:
2009:
2005:
2001:
1997:
1990:
1987:
1982:
1981:Sigma-Aldrich
1978:
1972:
1969:
1962:
1957:
1942:
1927:
1907:
1906:
1905:
1903:
1902:
1897:
1893:
1889:
1888:2-oxopropanal
1885:
1877:
1875:
1873:
1864:
1859:
1854:
1849:
1843:
1842:
1841:
1839:
1835:
1831:
1821:
1816:
1811:
1803:
1801:
1799:
1795:
1791:
1787:
1783:
1779:
1772:Condensations
1771:
1766:
1764:
1762:
1758:
1754:
1750:
1746:
1744:
1739:
1735:
1705:
1656:
1655:
1654:
1652:
1648:
1644:
1643:ethyl acetate
1629:
1592:
1591:
1590:
1581:
1565:
1561:
1556:
1554:
1549:
1547:
1539:
1537:
1535:
1531:
1527:
1523:
1519:
1518:organolithium
1515:
1511:
1507:
1496:
1492:
1484:
1480:
1476:
1472:
1468:
1462:
1458:
1456:
1453:
1449:
1445:
1441:
1437:
1433:
1429:
1425:
1421:
1417:
1404:
1366:
1365:
1364:
1362:
1337:
1333:
1323:
1320:
1317:
1316:
1312:
1309:
1306:
1302:
1301:
1297:
1294:
1291:
1287:
1286:
1282:
1279:
1276:
1272:
1271:
1265:
1261:
1258:
1255:
1254:
1248:
1246:
1244:
1240:
1233:
1228:
1226:
1222:
1215:
1211:
1207:
1200:
1197:
1196:keto and enol
1189:
1180:
1178:
1175:
1174:
1170:
1168:
1165:
1164:
1160:
1158:
1150:
1149:
1145:
1143:
1140:
1139:
1135:
1133:
1130:
1129:
1125:
1123:
1120:
1119:
1115:
1113:
1110:
1109:
1103:
1100:
1097:
1096:
1090:
1085:
1083:
1081:
1077:
1063:
1059:
1040:
1036:
1035:Acetylacetone
1024:
1017:
1012:
995:
989:
985:
983:
980:
979:
975:
972:
966:
965:
961:
959:
956:
955:
948:
941:
934:
910:
907:
906:
902:
901:
755:
752:
748:
747:
709:
706:
702:
701:
698:
695:
692:
688:
687:
683:
678:
673:
668:
664:
661:
657:
656:
652:
650:
645:
640:
636:
632:
628:
627:
623:
620:
616:
615:
611:
609:
608:Boiling point
606:
605:
601:
599:
598:Melting point
596:
595:
591:
589:
586:
585:
581:
578:
577:
570:
568:
565:
564:
543:
540:
536:
535:
530:
522:
518:
515:CC(=O)CC(=O)C
513:
510:O=C(C)CC(=O)C
508:
504:
497:
483:
473:
469:
462:
454:
450:
449:DTXSID4021979
446:
445:
443:
433:
429:
428:
424:
422:
419:
418:
411:
407:
406:
404:
402:
399:
398:
391:
390:
388:
386:
383:
382:
375:
371:
370:
368:
362:
358:
357:
350:
346:
345:
343:
341:
338:
337:
333:
330:
326:
325:
318:
317:
315:
313:
308:
307:
303:
299:
296:
294:
292:ECHA InfoCard
289:
288:
281:
277:
276:
274:
272:
269:
268:
261:
257:
256:
254:
252:
249:
248:
241:
237:
236:
234:
232:
229:
228:
224:
221:
217:
216:
209:
204:
201:
198:
194:
191:
187:
186:
184:
180:
175:
174:
167:
163:
162:
160:
157:
153:
152:
147:
139:
136:
135:
130:
126:
121:
116:
112:
107:
96:
92:
86:
82:
81:
77:
66:
62:
56:
52:
51:
47:
43:
38:
30:
19:
2723:Rh(acac)(CO)
2451:
2357:
2353:
2347:
2339:
2313:
2296:
2290:
2252:
2246:
2221:
2217:
2200:
2181:
2162:
2156:
2139:
2133:
2127:
2102:
2096:
2090:
2065:
2059:
2049:
2032:
2028:
2022:
1995:
1989:
1980:
1971:
1899:
1881:
1869:
1862:
1857:
1852:
1847:
1828:
1778:condensation
1775:
1742:
1731:
1715:] + HCl → CH
1711:C(O)CHC(O)CH
1690:C(O)CHC(O)CH
1625:
1589:) catalyst:
1557:
1550:
1543:
1532:atom at the
1505:
1494:
1478:
1474:
1466:
1463:recommended
1459:
1413:
1358:
1329:
1263:
1231:
1229:
1213:
1193:
1101:
1034:
1033:
969:Autoignition
904:
696:
648:
385:RTECS number
260:ChEMBL191625
149:Identifiers
132:Other names
124:
119:
2205:Stary, J.;
2135:Tetrahedron
1882:The enzyme
1822:of VO(acac)
1794:pyrimidines
1740:(dbaH) and
1686:→ Na[CH
1540:Preparation
1522:deprotonate
1122:Cyclohexane
1091:Tautomerism
1078:as well as
971:temperature
958:Flash point
691:Signal word
592:0.975 g/mL
579:Appearance
532:Properties
298:100.004.214
240:CHEBI:14750
125:(keto form)
120:(enol form)
115:IUPAC names
3106:Categories
2013:0471936235
1963:References
1649:(e.g., by
1534:position 1
1516:, such as
1440:bond order
1239:vinylogous
1086:Properties
986:2.4–11.6%
660:Pictograms
567:Molar mass
410:46R950BP4J
271:ChemSpider
177:3D model (
156:CAS Number
3112:Diketones
2439:complexes
1792:provides
1786:pyrazoles
1784:produces
1782:Hydrazine
1767:Reactions
1747:analogue
1707:Na[CH
1526:alkylated
1452:bidentate
1432:resonance
1332:weak acid
1235:keto→enol
1217:keto→enol
1199:tautomers
1112:Gas phase
1105:keto→enol
1051:−C(=O)−CH
1047:−C(=O)−CH
889:P403+P235
885:P403+P233
881:P370+P378
869:P337+P313
845:P308+P313
841:P307+P311
833:P304+P340
825:P302+P352
821:P301+P312
651:labelling
521:Enol form
421:UN number
392:SA1925000
319:204-634-0
311:EC Number
203:Enol form
3038:Yb(acac)
3030:Tm(acac)
3022:Er(acac)
3014:Ho(acac)
3006:Dy(acac)
2998:Tb(acac)
2990:Gd(acac)
2982:Eu(acac)
2967:Sm(acac)
2956:Nd(acac)
2948:Pr(acac)
2940:Ce(acac)
2932:La(acac)
2841:Tl(acac)
2827:Pt(acac)
2819:Ir(acac)
2799:Hf(acac)
2791:Lu(acac)
2780:Ba(acac)
2752:In(acac)
2738:Pd(acac)
2730:Rh(acac)
2715:Ru(acac)
2689:Zr(acac)
2648:Ga(acac)
2640:Zn(acac)
2632:Cu(acac)
2617:Co(acac)
2610:Co(acac)
2602:Fe(acac)
2595:Fe(acac)
2584:Cr(acac)
2577:Cr(acac)
2569:VO(acac)
2554:Ti(acac)
2543:Ti(acac)
2535:Sc(acac)
2502:Al(acac)
2494:Na(acac)
2384:12379146
2328:handout"
2320:"Co(tfa)
2238:96848983
2209:(1982).
2189:Archived
2082:16417375
1892:iron(II)
1694:] + 2 CH
1666:ONa + CH
1508: =
1424:hydrogen
1206:symmetry
1062:tautomer
1058:diketone
905:NFPA 704
642:Hazards
633:(χ)
166:123-54-6
3122:Ligands
2975:Eu(fod)
2923:
2681:Y(acac)
2562:V(acac)
2452:H(acac)
2375:1223103
2107:Bibcode
1798:NacNacs
1670:C(O)OCH
1560:acetone
1528:at the
1428:C3 atom
1290:dioxane
1275:ethanol
1256:Solvent
1132:Toluene
1098:Solvent
1016:what is
1014: (
588:Density
572:100.117
361:PubChem
225:741937
205::
2704:(acac)
2382:
2372:
2269:
2236:
2169:
2080:
2010:
1745:-butyl
1727:+ NaCl
1723:C(O)CH
1719:C(O)CH
1682:C(O)CH
1653:HCl):
1618:C(O)CH
1614:C(O)CH
1606:C(O)CH
1602:O + CH
1530:carbon
1455:ligand
1444:oxygen
1324:13.41
1313:10.16
1307:/water
1292:/water
1277:/water
1037:is an
1011:verify
1008:
697:Danger
503:SMILES
349:C15499
251:ChEMBL
109:Names
3132:Enols
2331:(PDF)
2299:: 6.
2234:S2CID
2214:(PDF)
1598:C(O))
1572:C(O))
1514:bases
1499:NaClO
1487:NaClO
1461:IUPAC
1336:anion
1298:12.5
1181:0.23
1177:Water
1116:11.7
468:InChI
425:2310
374:31261
334:2537
280:29001
231:ChEBI
179:JSmol
137:Hacac
2380:PMID
2267:ISBN
2167:ISBN
2078:PMID
2008:ISBN
1896:zinc
1838:base
1790:Urea
1755:and
1743:tert
1678:+ CH
1610:→ CH
1408:acac
1360:acac
1318:DMSO
1305:DMSO
1303:80%
1288:70%
1283:9.8
1273:40%
1259:T/°C
1194:The
1167:DMSO
1161:5.7
1153:CDCl
1146:7.2
897:P501
893:P405
877:P363
873:P361
865:P330
861:P322
857:P321
853:P312
849:P311
817:P281
813:P280
809:P273
805:P271
801:P270
797:P264
793:P261
789:P260
785:P243
781:P242
777:P241
773:P240
769:P233
765:P210
761:P202
757:P201
743:H412
739:H370
735:H341
731:H335
727:H331
723:H320
719:H311
715:H302
711:H226
401:UNII
340:KEGG
3089:No
3086:Md
3083:Fm
3080:Es
3077:Cf
3074:Bk
3071:Cm
3068:Am
3065:Pu
3062:Np
3056:Pa
3053:Th
3050:Ac
3047:**
2963:Pm
2916:Og
2913:Ts
2910:Lv
2907:Mc
2904:Fl
2901:Nh
2898:Cn
2895:Rg
2892:Ds
2889:Mt
2886:Hs
2883:Bh
2880:Sg
2877:Db
2874:Rf
2871:Lr
2868:**
2865:Ra
2862:Fr
2857:Rn
2854:At
2851:Po
2848:Bi
2845:Pb
2837:Hg
2834:Au
2815:Os
2812:Re
2806:Ta
2776:Cs
2771:Xe
2765:Te
2762:Sb
2759:Sn
2748:Cd
2745:Ag
2711:Tc
2700:MoO
2696:Nb
2675:Sr
2672:Rb
2667:Kr
2664:Br
2661:Se
2658:As
2655:Ge
2591:Mn
2529:Ca
2521:Ar
2518:Cl
2509:Si
2498:Mg
2488:Ne
2470:Be
2467:Li
2462:He
2370:PMC
2362:doi
2358:369
2301:doi
2259:doi
2226:doi
2144:doi
2115:doi
2070:doi
2066:128
2037:doi
2000:doi
1840::
1639:ONa
1594:(CH
1568:(CH
1397:+ H
1380:⇌ C
1363:):
1142:THF
1136:10
1126:42
649:GHS
437:EPA
364:CID
3108::
3059:U
2928:*
2809:W
2787:*
2768:I
2547:Cl
2526:K
2515:S
2512:P
2485:F
2482:O
2479:N
2476:C
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