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Indane-1,2,3-trione

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Indane-1,2,3-trione, which reacts readily with nucleophiles (including water). Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent
355: 327: 433: 230: 429: 205: 550:. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange. 421: 417: 395: 169: 461: 346: 484: 94: 125: 453: 566: 449: 437: 369: 339: 36: 186: 596: 409: 60: 401: 413: 500: 253: 441: 114: 425: 190: 70: 478: 590: 312: 469: 405: 546:(2-(1,3-dioxoindan-2-yl)iminoindane-1,3-dione), the amine must condense to give a 157: 547: 543: 387: 457: 281: 105: 383: 532: 23: 302: 144: 126: 379: 477:
Except where otherwise noted, data are given for materials in their
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InChI=1S/C9H4O3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4H
515:. The compound is the dehydrated derivative of C 156: 69: 8: 317:338.4 °C (641.1 °F; 611.5 K) 189: 113: 15: 535:, which is used to reveal fingerprints. 558: 235: 210: 185: 217:Key: WVZWEMOFSIEEMU-UHFFFAOYSA-N 7: 147: 14: 345: 265: 22: 481:(at 25 °C , 100 kPa). 271: 259: 1: 613: 542:To generate the ninhydrin 475: 326: 321: 246: 226: 201: 53: 45: 35: 30: 21: 571:pubchem.ncbi.nlm.nih.gov 396:Precautionary statements 238:O=C2c1ccccc1C(=O)C2=O 567:"Indan-1,2,3-trione" 17:Indane-1,2,3-trione 497:Indane-1,2,3-trione 289: g·mol 40:Indane-1,2,3-trione 18: 503:with the formula C 485:Infobox references 16: 539:carbonyl groups. 493:Chemical compound 491: 490: 370:Hazard statements 170:CompTox Dashboard 95:Interactive image 604: 582: 581: 579: 577: 563: 501:organic compound 471: 467: 463: 459: 455: 451: 447: 443: 439: 435: 431: 427: 423: 419: 415: 411: 407: 403: 389: 385: 381: 377: 349: 288: 273: 267: 261: 254:Chemical formula 194: 193: 178: 176: 160: 149: 128: 117: 97: 73: 26: 19: 612: 611: 607: 606: 605: 603: 602: 601: 587: 586: 585: 575: 573: 565: 564: 560: 556: 530: 526: 522: 518: 514: 510: 506: 494: 487: 482: 398: 372: 358: 342: 286: 276: 270: 264: 256: 242: 239: 234: 233: 222: 219: 218: 215: 209: 208: 197: 179: 172: 163: 150: 138: 120: 100: 87: 76: 63: 49: 41: 12: 11: 5: 610: 608: 600: 599: 589: 588: 584: 583: 557: 555: 552: 528: 524: 520: 516: 512: 508: 504: 492: 489: 488: 483: 479:standard state 476: 473: 472: 434:P305+P351+P338 399: 394: 391: 390: 373: 368: 365: 364: 359: 354: 351: 350: 343: 338: 335: 334: 324: 323: 319: 318: 315: 309: 308: 305: 299: 298: 295: 291: 290: 284: 278: 277: 274: 268: 262: 257: 252: 249: 248: 244: 243: 241: 240: 237: 229: 228: 227: 224: 223: 221: 220: 216: 213: 212: 204: 203: 202: 199: 198: 196: 195: 187:DTXSID40239655 182: 180: 168: 165: 164: 162: 161: 153: 151: 143: 140: 139: 137: 136: 132: 130: 122: 121: 119: 118: 110: 108: 102: 101: 99: 98: 90: 88: 81: 78: 77: 75: 74: 66: 64: 59: 56: 55: 51: 50: 47: 43: 42: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 609: 598: 595: 594: 592: 572: 568: 562: 559: 553: 551: 549: 545: 540: 536: 534: 502: 498: 486: 480: 474: 400: 397: 393: 392: 374: 371: 367: 366: 363: 360: 357: 353: 352: 348: 344: 341: 337: 336: 332: 330: 325: 320: 316: 314: 313:Boiling point 311: 310: 306: 304: 301: 300: 297:white powder 296: 293: 292: 285: 283: 280: 279: 258: 255: 251: 250: 245: 236: 232: 225: 211: 207: 200: 192: 188: 184: 183: 181: 171: 167: 166: 159: 155: 154: 152: 146: 142: 141: 134: 133: 131: 129: 124: 123: 116: 112: 111: 109: 107: 104: 103: 96: 92: 91: 89: 85: 80: 79: 72: 68: 67: 65: 62: 58: 57: 52: 44: 38: 34: 29: 25: 20: 574:. Retrieved 570: 561: 541: 537: 496: 495: 361: 328: 54:Identifiers 48:Indanetrione 46:Other names 548:Schiff base 544:chromophore 531:, known as 356:Signal word 307:1.482 g/cm 294:Appearance 247:Properties 597:Triketones 576:4 February 554:References 340:Pictograms 282:Molar mass 106:ChemSpider 82:3D model ( 61:CAS Number 37:IUPAC name 533:ninhydrin 462:P403+P233 454:P337+P313 450:P332+P313 430:P304+P340 426:P302+P352 422:P301+P312 331:labelling 135:213-340-1 127:EC Number 591:Category 322:Hazards 71:938-24-9 499:is the 362:Warning 303:Density 287:160.128 145:PubChem 231:SMILES 31:Names 527:C(OH) 206:InChI 158:70309 115:63492 84:JSmol 578:2022 523:(CO) 511:(CO) 470:P501 466:P405 458:P362 446:P330 442:P321 438:P312 418:P280 414:P271 410:P270 406:P264 402:P261 388:H335 384:H319 380:H315 376:H302 329:GHS 175:EPA 148:CID 593:: 569:. 468:, 464:, 460:, 456:, 452:, 448:, 444:, 440:, 436:, 432:, 428:, 424:, 420:, 416:, 412:, 408:, 404:, 386:, 382:, 378:, 333:: 580:. 529:2 525:2 521:4 519:H 517:6 513:3 509:4 507:H 505:6 275:3 272:O 269:4 266:H 263:9 260:C 177:) 173:( 86:)

Index


IUPAC name
CAS Number
938-24-9
JSmol
Interactive image
ChemSpider
63492
EC Number
PubChem
70309
CompTox Dashboard
DTXSID40239655
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InChI
SMILES
Chemical formula
Molar mass
Density
Boiling point
GHS labelling
Pictograms
GHS07: Exclamation mark
Signal word
Hazard statements
Precautionary statements
standard state
Infobox references
organic compound
ninhydrin

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