Knowledge (XXG)

Acetoacetanilide

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Gilli, Paola; Bertolasi, Valerio; Ferretti, Valeria; Gilli, Gastone (2000). "Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation".
440: 407: 650:. It is a white solid that is poorly soluble in water. This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic 573: 581: 305: 522: 595: 823: 588: 270: 510: 518: 100: 506: 615: 480: 213: 431: 234: 426: 472: 170: 526: 158: 120: 663: 454: 419: 36: 815: 498: 251: 66: 490: 530: 486: 696: 502: 891: 819: 868: 843: 811: 788: 761: 675: 391: 328: 222: 534: 514: 255: 162: 140: 76: 542: 686: 655: 609: 885: 705: 380: 151: 546: 690: 494: 202: 709: 23: 359: 131: 872: 847: 792: 721: 464: 279:
InChI=1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)
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InChI=1/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)
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Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide".
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Except where otherwise noted, data are given for materials in their
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Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril".
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Acetoacetylation with diketene followed by diazo coupling.
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83 to 88 °C (181 to 190 °F; 356 to 361 K)
658:. Acetoacetanilides usually exist as the keto-amide 685:To make the dyes, acetoacetanilides are coupled to 201: 808:Kirk-Othmer Encyclopedia of Chemical Technology 569: 75: 840:Ullmann's Encyclopedia of Industrial Chemistry 816:10.1002/0471238961.151807011001060605.a01.pub2 806:Jaffe, Edward E. (2004). "Pigments, Organic". 708:, acetoacetanilide dehydrates to give 4-methyl 8: 838:K. Hunger. W. Herbst "Pigments, Organic" in 646:. It is the acetoacetamide derivative of 630:is an organic compound with the formula CH 254: 161: 139: 15: 221: 754:Journal of the American Chemical Society 682:. Many analogues have been prepared. 743: 310: 275: 250: 152: 282:Key: DYRDKSSFIWVSNM-UHFFFAOYSA-N 119: 7: 292:Key: DYRDKSSFIWVSNM-UHFFFAOYAR 192: 14: 674:Acetoacetanilide is prepared by 430: 425: 346: 340: 22: 612:(at 25 °C , 100 kPa). 349: 334: 1: 842:, Wiley-VCH, Weinheim, 2012. 908: 670:Preparation and reactions 606: 406: 401: 321: 301: 266: 59: 51: 35: 30: 21: 873:10.15227/orgsyn.024.0068 848:10.1002/14356007.a20_371 793:10.15227/orgsyn.021.0004 481:Precautionary statements 313:CC(=O)CC(=O)NC1=CC=CC=C1 54:Acetoacetylaminobenzene 701: 576: 699: 664:X-ray crystallography 575: 558:(fire diamond) 37:Preferred IUPAC name 704:In the presence of 392:Solubility in water 367: g·mol 18: 702: 616:Infobox references 577: 16: 861:Organic Syntheses 825:978-0-471-48494-3 781:Organic Syntheses 766:10.1021/ja000921+ 678:of aniline using 624:Chemical compound 622: 621: 455:Hazard statements 375:Colourless solid 235:CompTox Dashboard 101:Interactive image 45:-phenylbutanamide 17:Acetoacetanilide 899: 877: 876: 856: 850: 836: 830: 829: 803: 797: 796: 776: 770: 769: 748: 676:acetoacetylation 628:Acetoacetanilide 597: 590: 583: 568: 548: 544: 540: 536: 532: 528: 524: 520: 516: 512: 508: 504: 500: 496: 492: 488: 474: 470: 466: 462: 434: 429: 366: 351: 348: 342: 336: 329:Chemical formula 259: 258: 243: 241: 225: 205: 194: 173: 165: 154: 143: 123: 103: 79: 26: 19: 907: 906: 902: 901: 900: 898: 897: 896: 882: 881: 880: 858: 857: 853: 837: 833: 826: 805: 804: 800: 778: 777: 773: 750: 749: 745: 741: 733: 729: 725: 718: 687:diazonium salts 672: 656:arylide yellows 645: 641: 637: 633: 625: 618: 613: 602: 601: 600: 599: 592: 585: 578: 574: 566: 483: 457: 443: 422: 394: 364: 354: 345: 339: 331: 317: 314: 309: 308: 297: 294: 293: 290: 284: 283: 280: 274: 273: 262: 244: 237: 228: 208: 195: 183: 146: 126: 106: 93: 82: 69: 55: 47: 46: 12: 11: 5: 905: 903: 895: 894: 884: 883: 879: 878: 851: 831: 824: 798: 771: 742: 740: 737: 736: 735: 731: 727: 723: 717: 714: 671: 668: 643: 639: 635: 631: 623: 620: 619: 614: 610:standard state 607: 604: 603: 593: 586: 579: 564: 563: 562: 561: 559: 550: 549: 484: 479: 476: 475: 458: 453: 450: 449: 444: 439: 436: 435: 423: 418: 415: 414: 404: 403: 399: 398: 395: 390: 387: 386: 383: 377: 376: 373: 369: 368: 362: 356: 355: 352: 343: 337: 332: 327: 324: 323: 319: 318: 316: 315: 312: 304: 303: 302: 299: 298: 296: 295: 291: 288: 287: 285: 281: 278: 277: 269: 268: 267: 264: 263: 261: 260: 247: 245: 233: 230: 229: 227: 226: 218: 216: 210: 209: 207: 206: 198: 196: 188: 185: 184: 182: 181: 177: 175: 167: 166: 156: 148: 147: 145: 144: 136: 134: 128: 127: 125: 124: 116: 114: 108: 107: 105: 104: 96: 94: 87: 84: 83: 81: 80: 72: 70: 65: 62: 61: 57: 56: 53: 49: 48: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 904: 893: 890: 889: 887: 874: 870: 866: 862: 855: 852: 849: 845: 841: 835: 832: 827: 821: 817: 813: 809: 802: 799: 794: 790: 786: 782: 775: 772: 767: 763: 759: 755: 747: 744: 738: 734: 720: 719: 715: 713: 711: 707: 706:sulfuric acid 698: 694: 692: 688: 683: 681: 677: 669: 667: 665: 662:according to 661: 657: 653: 649: 629: 617: 611: 605: 598: 591: 584: 560: 557: 556: 552: 551: 485: 482: 478: 477: 459: 456: 452: 451: 448: 445: 442: 438: 437: 433: 428: 424: 421: 417: 416: 412: 410: 405: 400: 396: 393: 389: 388: 384: 382: 381:Melting point 379: 378: 374: 371: 370: 363: 361: 358: 357: 333: 330: 326: 325: 320: 311: 307: 300: 286: 276: 272: 265: 257: 253: 252:DTXSID0024397 249: 248: 246: 236: 232: 231: 224: 220: 219: 217: 215: 212: 211: 204: 200: 199: 197: 191: 187: 186: 179: 178: 176: 174: 169: 168: 164: 160: 157: 155: 153:ECHA InfoCard 150: 149: 142: 138: 137: 135: 133: 130: 129: 122: 121:ChEMBL1604429 118: 117: 115: 113: 110: 109: 102: 98: 97: 95: 91: 86: 85: 78: 74: 73: 71: 68: 64: 63: 58: 50: 44: 38: 34: 29: 25: 20: 864: 860: 854: 839: 834: 807: 801: 784: 780: 774: 757: 753: 746: 710:-2-quinolone 703: 691:azo coupling 684: 673: 627: 626: 554: 446: 408: 60:Identifiers 52:Other names 42: 441:Signal word 372:Appearance 322:Properties 159:100.002.725 739:References 420:Pictograms 360:Molar mass 223:W35JB9PY3X 132:ChemSpider 88:3D model ( 67:CAS Number 523:P304+P340 519:P304+P312 515:P302+P352 511:P301+P312 411:labelling 180:202-996-4 172:EC Number 892:Anilides 886:Category 716:See also 680:diketene 660:tautomer 652:pigments 555:NFPA 704 402:Hazards 77:102-01-2 654:called 648:aniline 638:C(O)NHC 447:Warning 365:177.203 190:PubChem 867:: 68. 822:  760:(42). 634:C(O)CH 306:SMILES 112:ChEMBL 41:3-Oxo- 31:Names 787:: 4. 271:InChI 90:JSmol 820:ISBN 547:P501 543:P363 539:P330 535:P322 531:P314 527:P312 507:P280 503:P271 499:P270 495:P264 491:P261 487:P260 473:H373 469:H332 465:H312 461:H302 397:low 214:UNII 203:7592 141:7311 869:doi 844:doi 812:doi 789:doi 762:doi 758:122 693:". 689:, " 409:GHS 240:EPA 193:CID 888:: 865:24 863:. 818:. 810:. 785:21 783:. 756:. 730:NO 728:11 724:10 712:. 666:. 545:, 541:, 537:, 533:, 529:, 525:, 521:, 517:, 513:, 509:, 505:, 501:, 497:, 493:, 489:, 471:, 467:, 463:, 413:: 344:11 338:10 875:. 871:: 846:: 828:. 814:: 795:. 791:: 768:. 764:: 732:2 726:H 722:C 644:5 642:H 640:6 636:2 632:3 596:0 589:1 582:2 353:2 350:O 347:N 341:H 335:C 242:) 238:( 92:) 43:N

Index


Preferred IUPAC name
CAS Number
102-01-2
JSmol
Interactive image
ChEMBL
ChEMBL1604429
ChemSpider
7311
ECHA InfoCard
100.002.725
Edit this at Wikidata
EC Number
PubChem
7592
UNII
W35JB9PY3X
CompTox Dashboard
DTXSID0024397
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Melting point
Solubility in water
GHS labelling
Pictograms
GHS07: Exclamation mark

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