887:
33:
24:
339:
200:
615:
682:
678:
796:
681:
1038:
Ethyl acetoacetate transesterifies to give benzyl acetoacetate via a mechanism involving acetylketene. Ethyl (and other) acetoacetates nitrosate readily with equimolar sodium nitrite in acetic acid, to afford the corresponding oximinoacetoacetate esters. A dissolving-zinc reduction of these in acetic
1202:
699:
623:
1315:
Jane L. Burdett; Max T. Rogers (1964). "Keto-Enol
Tautomerism in β-Dicarbonyls Studied by Nuclear Magnetic Resonance Spectroscopy. I. Proton Chemical Shifts and Equilibrium Constants of Pure Compounds".
1280:
Tan, Da-Zhi; Li, Ming-Ze; Xiong, Wan-nan; Xu, Yi-Xuan; Pan, Yang; Fan, Wen-Jie; Jiang, Wen-Feng (2023). "Improvement of the Ethyl
Acetoacetate Preparation Experiment: A Green Chemistry Experiment".
595:
988:
The dianion of ethyl acetoacetate is also a useful building block, except that the electrophile adds to the terminal carbon. The strategy can be depicted in the following simplified form:
683:
657:
684:
692:
809:
388:
1406:
Adkins, Homer; Connor, Ralph; Cramer, Howard (1930). "The
Hydrogenation of Acetoacetic Ester and Certain of Its Derivatives over Nickel".
1346:
Jin, Yinghua; Roberts, Frank G.; Coates, Robert M. (2007). "Stereoselective
Isoprenoid Chain Extension with Acetoacetate Dianion: [(
804:
1522:
1450:
886:
1581:
1390:
353:
816:
1235:
117:
1576:
1505:
Panten, Johannes; Surburg, Horst (2016). "Flavors and
Fragrances, 3. Aromatic and Heterocyclic Compounds".
651:
286:
195:
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317:
157:
614:
522:
1198:
962:
207:
978:
334:
1566:
1040:
982:
974:
873:
The small scale preparation of ethyl acetoacetate is a classic laboratory procedure. It involves
558:
881:. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.
1466:
Urs, Usha K.; Shalini, K.; Shivashankar, S. A.; Guru Row, T. N. (2000). "Low-Temperature Tris(
177:
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1178:
Ethyl acetoacetate has low toxicity to animals. It is highly biodegradable.
1051:
909:
908:
The enol is moderately acidic. Thus ethyl acetoacetate behaves similarly to
905:. In the neat liquid at 33 °C, the enol consists of 15% of the total.
878:
770:
742:
488:
478:
188:
862:
At large scale, ethyl acetoacetate is industrially produced by treatment of
840:
711:
1419:
1329:
691:
698:
434:
208:
168:
1218:
Riemenschneider, Wilhelm; Bolt, Hermann M. (2005). "Esters, Organic".
1044:
306:
1085:
Two ketals of ethyl acetoacetate are used in commercial fragrances.
1039:
acid in the presence of ketoesters or beta-diketones constitute the
786:
Except where otherwise noted, data are given for materials in their
1089:
863:
775:
664:
234:
116:
1472:
1250:
867:
765:
468:
246:
1251:
J. K. H. Inglis and K. C. Roberts (1926). "Ethyl
Acetoacetate".
1035:
Reduction of ethyl acetoacetate gives ethyl 3-hydroxybutyrate.
148:
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1028:
843:
728:
457:
270:
128:
106:
1314:
322:
643:
452:
225:
1173:
461:
1433:
Charles, R. G.; Peterson, N. C.; Franke, G. H. (1967).
1054:, ethyl acetoacetate forms chelate complexes, such as
1432:
1437:. Inorganic Syntheses. Vol. 9. pp. 25–27.
1217:
854:in the production of a wide variety of compounds.
850:. It is a colorless liquid. It is widely used as a
1405:
1553:
1345:
362:InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
258:
680:
372:InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
92:
1507:Ullmann's Encyclopedia of Industrial Chemistry
1220:Ullmann's Encyclopedia of Industrial Chemistry
1504:
1385:(Sixth ed.). New York, NY: McGraw-Hill.
1279:
1203:Institute for Occupational Safety and Health
493:180.8 °C (357.4 °F; 453.9 K)
981:. After its alkylation and saponification,
965:. Ethyl acetoacetate is often used in the
337:
198:
176:
1435:Aluminum Derivative of Ethyl Acetoacetate
294:
1408:Journal of the American Chemical Society
1542:International Chemical Safety Card 1024
1174:Safety and environmental considerations
333:
1554:
483:−45 °C (−49 °F; 228 K)
189:
1380:
1341:
1339:
1213:
1211:
716:70 °C (158 °F; 343 K)
365:Key: XYIBRDXRRQCHLP-UHFFFAOYSA-N
156:
136:
375:Key: XYIBRDXRRQCHLP-UHFFFAOYAP
249:
233:
13:
1470:-butyl 3-oxobutanoato)iron(III)".
1336:
1208:
961:The resulting carbanion undergoes
885:
676:
14:
1593:
1535:
901:Ethyl acetoacetate is subject to
890:Preparation of ethyl acetoacetate
1043:, useful for the preparation of
794:
613:
31:
22:
1498:
1459:
790:(at 25 °C , 100 kPa).
1426:
1399:
1374:
1308:
1273:
1244:
1188:
857:
68:3-Oxobutanoic acid ethyl ester
1:
1282:Journal of Chemical Education
1228:10.1002/14356007.a09_565.pub2
1181:
1169:), the propylene glycol ketal
1127:), the ethylene glycol ketal
1077:and the Fe(III) derivative.
896:
62:Acetoacetic acid ethyl ester
7:
1302:10.1021/acs.jchemed.2c00718
1080:
967:acetoacetic ester synthesis
10:
1598:
1547:Inchem properties database
1381:Carey, Francis A. (2006).
1205:, accessed on 2021-12-19.
439:130.14 g/mol
1492:10.1107/S010827010001249X
1443:10.1002/9780470132401.ch8
1199:GESTIS Substance Database
963:nucleophilic substitution
784:
720:
594:
589:
404:
384:
349:
76:
56:
44:
39:
30:
21:
1582:Sweet-smelling chemicals
1515:10.1002/14356007.t11_t02
1368:10.15227/orgsyn.084.0043
1350:)-Geranylgeraniol from (
1267:10.15227/orgsyn.006.0036
979:Knoevenagel condensation
652:Precautionary statements
1222:. Weinheim: Wiley-VCH.
1041:Knorr pyrrole synthesis
983:thermal decarboxylation
975:malonic ester synthesis
559:Magnetic susceptibility
1050:Another similarity to
891:
687:
903:keto-enol tautomerism
889:
852:chemical intermediate
686:
985:is also possible.
875:Claisen condensation
669:(fire diamond)
50:Ethyl 3-oxobutanoate
46:Preferred IUPAC name
1577:Acetoacetate esters
1484:2000AcCrC..56E.448U
1420:10.1021/ja01375a082
1330:10.1021/ja01065a003
1294:2023JChEd.100..811T
738:Methyl acetoacetate
500:Solubility in water
473:1.030 g/cm, liquid
65:Ethyl acetylacetate
18:
17:Ethyl acetoacetate
892:
833:ethyl acetoacetate
817:Infobox references
721:Related compounds
688:
447:Colourless liquid
16:
1524:978-3-527-30673-2
1509:. pp. 1–45.
1478:(10): e448–e449.
1452:978-0-470-13168-8
1414:(12): 5192–5198.
1383:Organic Chemistry
1356:Organic Syntheses
1254:Organic Syntheses
825:Chemical compound
823:
822:
758:Related compounds
638:Hazard statements
318:CompTox Dashboard
118:Interactive image
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971:diethyl malonate
969:, comparable to
957:
848:acetoacetic acid
830:organic compound
807:
801:
798:
797:
748:Diethyl malonate
701:
694:
679:
659:
645:
617:
572:Refractive index
565:−71.67×10cm/mol
516:
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412:Chemical formula
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1536:External links
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788:standard state
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1392:0-07-111562-5
1388:
1384:
1377:
1369:
1365:
1361:
1357:
1354:)-Farnesol".
1353:
1349:
1342:
1340:
1331:
1327:
1324:: 2105–2109.
1323:
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1311:
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1086:
1078:
1053:
1052:acetylacetone
1048:
1046:
1042:
1036:
1030:
1009:+ BuLi → LiCH
991:
990:
989:
986:
984:
980:
976:
972:
968:
964:
915:
914:
913:
911:
910:acetylacetone
906:
904:
888:
884:
883:
882:
880:
879:ethyl acetate
876:
871:
869:
865:
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853:
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772:
771:Acetylacetone
769:
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755:
749:
746:
744:
743:Ethyl acetate
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489:Boiling point
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479:Melting point
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190:ECHA InfoCard
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1562:Ethyl esters
1506:
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1084:
1049:
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1034:
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872:
861:
836:
832:
827:
665:
629:
596:
575:
526:
271:RTECS number
158:ChEMBL169176
77:Identifiers
57:Other names
1130:Fraistone (
858:Preparation
712:Flash point
624:Signal word
538:10.68 (in H
444:Appearance
405:Properties
196:100.005.015
1556:Categories
1237:3527306730
1182:References
1045:porphyrins
1013:C(O)CHNaCO
997:C(O)CHNaCO
941:C(O)CHNaCO
937:+ NaH → CH
608:Pictograms
435:Molar mass
296:IZP61H3TB1
169:ChemSpider
138:CHEBI:4893
105:3D model (
84:CAS Number
897:Reactions
839:) is the
599:labelling
545:14.2 (in
307:UN number
278:AK5250000
217:205-516-1
209:EC Number
1090:Fructone
1081:See also
1060:C(O)CHCO
864:diketene
776:Diketene
727:Related
666:NFPA 704
590:Hazards
561:(χ)
178:13865426
94:141-97-9
1572:Flavors
1480:Bibcode
1348:E, E, E
1290:Bibcode
1201:of the
1197:in the
1195:Record
977:or the
973:in the
868:ethanol
810:what is
808: (
766:Acetone
630:Warning
523:Acidity
469:Density
429:
247:PubChem
1521:
1449:
1389:
1362:: 43.
1261:: 36.
1234:
1027:(Bu =
921:C(O)CH
805:verify
802:
729:esters
585:1.420
515:
513:ml (20
511:
507:
389:SMILES
235:C03500
149:ChEMBL
40:Names
1056:Al(CH
1029:butyl
1025:+ BuH
866:with
844:ester
841:ethyl
509:g/100
458:Fruit
354:InChI
311:1993
129:ChEBI
107:JSmol
1519:ISBN
1468:tert
1447:ISBN
1387:ISBN
1352:E, E
1232:ISBN
828:The
644:H319
547:DMSO
517:°C)
505:2.86
453:Odor
287:UNII
260:8868
226:KEGG
1511:doi
1488:doi
1439:doi
1416:doi
1364:doi
1326:doi
1298:doi
1286:100
1263:doi
1224:doi
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837:EAA
597:GHS
462:rum
460:or
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1134:3
1124:5
1122:H
1120:2
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1116:2
1112:2
1108:4
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1021:H
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1007:5
1005:H
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955:2
951:5
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