Knowledge (XXG)

Disiamylborane

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Chandrasekharan, J.; Brown, Herbert C. (1985). "Hydroboration kinetics. 11. A reinvestigation of the kinetics of hydroboration of representative alkenes with disiamylborane dimer. Conclusive evidence for the dissociation mechanism in the hydroboration of alkenes with dialkylborane dimers".
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Disiamylborane is relatively selective for terminal alkynes and alkenes vs internal alkynes and alkenes. Like most
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Eric J. Leopold (1986). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol".
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The hydroboration process proceeds via an initial dissociation of the dimer.
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Except where otherwise noted, data are given for materials in their
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InChI=1S/C10H23B/c1-7(2)9(5)11-10(6)8(3)4/h7-11H,1-6H3
397:, it has a dimeric structure with bridging hydrides. 225:
InChI=1/C10H23B/c1-7(2)9(5)11-10(6)8(3)4/h7-11H,1-6H3
385:BH). It is a colorless waxy solid that is used in 461:), a primary borane obtained by hydroboration of 137: 61: 8: 428:manner. It can be used to convert terminal 504: 502: 190: 112: 15: 157: 377: 373: 369: 365: 361: 498: 246: 211: 186: 354:(bis(1,2-dimethylpropyl)borane) is an 457:((1,1,2-trimethylpropyl)borane, ThxBH 218:Key: HXJFQNUWPUICNY-UHFFFAOYSA-N 7: 228:Key: HXJFQNUWPUICNY-UHFFFAOYAY 128: 14: 391:hydroboration–oxidation reactions 541:The Journal of Organic Chemistry 317: 22: 313:(at 25 Â°C , 100 kPa). 577:Reagents for organic chemistry 424:, the addition proceeds in an 405:Disiamylborane is prepared by 1: 40:Bis(1,2-dimethylpropyl)borane 593: 478:is an abbreviation for "di 293:154.09 g/mol 307: 262: 237: 202: 45: 35: 30: 21: 525:10.15227/orgsyn.064.0164 393:. Like most dialkyl 254:B(C(C(C)C)C)C(C)C(C)C 553:10.1021/jo00204a019 463:tetramethylethylene 449:9-Borabicyclononane 249:CC(C(C)C)BC(C)C(C)C 18: 381:(abbreviation: Sia 340:Infobox references 16: 512:Organic Syntheses 411:trimethylethylene 387:organic synthesis 358:with the formula 348:Chemical compound 346: 345: 171:CompTox Dashboard 94:Interactive image 87:Interactive image 584: 557: 556: 535: 529: 527: 506: 443:Related reagents 426:anti-Markovnikov 380: 330: 324: 321: 320: 270:Chemical formula 195: 194: 179: 177: 161: 141: 130: 116: 96: 89: 65: 26: 19: 592: 591: 587: 586: 585: 583: 582: 581: 562: 561: 560: 537: 536: 532: 508: 507: 500: 496: 472: 460: 445: 403: 384: 379: 375: 371: 367: 363: 359: 349: 342: 337: 336: 335:  ?) 326: 322: 318: 314: 282: 278: 272: 258: 255: 250: 245: 244: 233: 230: 229: 226: 220: 219: 216: 210: 209: 198: 180: 173: 164: 144: 131: 119: 99: 79: 68: 55: 41: 17:Disiamylborane 12: 11: 5: 590: 588: 580: 579: 574: 564: 563: 559: 558: 547:(4): 518–520. 530: 497: 495: 492: 471: 468: 467: 466: 458: 452: 444: 441: 402: 399: 395:boron hydrides 382: 352:Disiamylborane 347: 344: 343: 338: 316: 315: 311:standard state 308: 305: 304: 301: 295: 294: 291: 285: 284: 280: 276: 273: 268: 265: 264: 260: 259: 257: 256: 253: 251: 248: 240: 239: 238: 235: 234: 232: 231: 227: 224: 223: 221: 217: 214: 213: 205: 204: 203: 200: 199: 197: 196: 188:DTXSID40910174 183: 181: 169: 166: 165: 163: 162: 154: 152: 146: 145: 143: 142: 134: 132: 124: 121: 120: 118: 117: 109: 107: 101: 100: 98: 97: 90: 82: 80: 73: 70: 69: 67: 66: 58: 56: 51: 48: 47: 43: 42: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 589: 578: 575: 573: 570: 569: 567: 554: 550: 546: 542: 534: 531: 526: 522: 518: 514: 513: 505: 503: 499: 493: 491: 489: 485: 481: 477: 469: 464: 456: 453: 450: 447: 446: 442: 440: 437: 435: 431: 427: 423: 422:hydroboration 418: 416: 412: 408: 407:hydroboration 400: 398: 396: 392: 388: 357: 353: 341: 334: 329: 312: 306: 302: 300: 299:Melting point 297: 296: 292: 290: 287: 286: 274: 271: 267: 266: 261: 252: 247: 243: 236: 222: 212: 208: 201: 193: 189: 185: 184: 182: 172: 168: 167: 160: 156: 155: 153: 151: 148: 147: 140: 136: 135: 133: 127: 123: 122: 115: 111: 110: 108: 106: 103: 102: 95: 91: 88: 84: 83: 81: 77: 72: 71: 64: 60: 59: 57: 54: 50: 49: 44: 38: 34: 29: 25: 20: 572:Alkylboranes 544: 540: 533: 516: 510: 487: 479: 475: 473: 455:Thexylborane 438: 419: 404: 356:organoborane 351: 350: 46:Identifiers 474:The prefix 263:Properties 566:Categories 494:References 289:Molar mass 159:2O6VD8483R 105:ChemSpider 74:3D model ( 53:CAS Number 37:IUPAC name 486:", where 434:aldehydes 401:Reactions 360:[((CH 303:35-40 °C 63:1069-54-1 476:disiamyl 451:(9-BBN). 415:diborane 283:B 519:: 164. 432:, into 430:alkynes 368:CHCH(CH 333:what is 331: ( 126:PubChem 470:Naming 328:verify 325:  242:SMILES 139:192733 114:167251 31:Names 480:-sec- 413:with 207:InChI 76:JSmol 484:amyl 389:for 150:UNII 549:doi 521:doi 488:sec 482:iso 409:of 376:BH] 176:EPA 129:CID 568:: 545:50 543:. 517:64 515:. 501:^ 436:. 372:)) 281:23 277:10 555:. 551:: 528:. 523:: 465:. 459:2 383:2 378:2 374:2 370:3 366:2 364:) 362:3 323:N 279:H 275:C 178:) 174:( 78:)

Index

Skeletal formula of disiamylborane
IUPAC name
CAS Number
1069-54-1
JSmol
Interactive image
Interactive image
ChemSpider
167251
PubChem
192733
UNII
2O6VD8483R
CompTox Dashboard
DTXSID40910174
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InChI
SMILES
Chemical formula
Molar mass
Melting point
standard state
verify
what is
Infobox references
organoborane
organic synthesis
hydroboration–oxidation reactions
boron hydrides
hydroboration

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