Knowledge (XXG)

Borate esters

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is typically added. Borate esters are volatile and can be purified by distillation. This procedure is used for analysis of trace amounts of borate and for analysis of boron in steel. Like all boron compounds, alkyl borates burn with a characteristic green flame. This property is used to determine the
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M.A. Beckett, G.C. Strickland, J.R. Holland, and K.S. Varma, "A convenient NMR method for the measurement of Lewis acidity at boron centres: correlation of reaction rates of Lewis acid initiated epoxide polymerizations with Lewis acidity",
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Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.; Larsen, R. D.; Reider, P. J. (2002). "An Improved Protocol for the Preparation of 3-Pyridyl- and Some Arylboronic Acids".
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Brown, Herbert C.; Mead, Edward J.; Shoaf, Charles J. (1956). "Convenient Procedures for the Preparation of Alkyl Borate Esters".
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and can initiate epoxide polymerization reactions. The Lewis acidity of orthoborate esters, as determined by the
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such as sugars and the reaction with mannitol forms the basis of a titrimetric analytical method for boric acid.
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for Suzuki couplings: Unsymmetrical borate esters are prepared from alkylation of trimethyl borate:
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Vogel's Textbook of Macro and Semimicro Qualitative Inorganic Analysis
501:{\displaystyle {\ce {ArMgBr + B(OCH3)3 -> MgBrOCH3 + ArB(OCH3)2}}} 688:
Mendham, J.; Denney, R. C.; Barnes, J. D.; Thomas, M. J. K. (2000),
341: 55: 627:{\displaystyle {\ce {ArB(OCH3)2 + 2H2O -> ArB(OH)2 + 2HOCH3}}} 358: 324:{\displaystyle {\ce {3 B(OH)3 + 3 ROH -> B3O3(OR)3 + 6 H2O}}} 191:{\displaystyle {\ce {B(OH)3 + 3 ROH -> B(OR)3 + 3 H2O}}} 620: 600: 570: 550: 537: 494: 481: 457: 441: 428: 314: 294: 273: 260: 234: 181: 161: 124: 692:(6th ed.), New York: Prentice Hall, p. 666, 42:
which are conveniently prepared by the stoichiometric
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R. L. Kidwell; M. Murphy & S. D. Darling (1969).
517: 402: 207: 101: 357:Borate esters form spontaneously when treated with 713: 626: 500: 323: 190: 27:Organic compounds of the form B(OR)₃ or B₃O₃(OR)₃ 8: 339:presence of boron in qualitative analysis. 334:A dehydrating agent, such as concentrated 619: 614: 609: 599: 594: 583: 569: 564: 559: 549: 544: 536: 531: 523: 518: 516: 493: 488: 480: 475: 467: 456: 451: 440: 435: 427: 422: 414: 403: 401: 313: 308: 303: 293: 288: 277: 272: 267: 259: 254: 243: 233: 228: 217: 212: 208: 206: 180: 175: 170: 160: 155: 144: 133: 123: 118: 107: 102: 100: 385: 381: 84: 80: 76: 65: 653: 54:. There are two main classes of borate 690:Vogel's Quantitative Chemical Analysis 712:Vogel, Arthur I.; Svehla, G. (1979), 7: 364:Metaborate esters show considerable 349:is a popular borate ester used in 88:. Metaborates contain 6-membered 25: 754:doi: 10.1016/0032-3861(96)00323-0 720:(5th ed.), London: Longman, 790:"Phenols: 6-Methoxy-2-naphthol" 769:. Vol. 67. p. 5394. 590: 584: 576: 540: 524: 484: 468: 444: 431: 415: 284: 278: 247: 224: 218: 151: 145: 137: 114: 108: 1: 389:, is used as a precursor to 843: 809:, vol. 10, p. 80 637:These esters hydrolyze to 628: 502: 370:Gutmann-Beckett method 354: 325: 192: 629: 503: 372:, is relatively low. 345: 326: 193: 44:condensation reaction 40:organoboron compounds 641:, which are used in 515: 400: 205: 99: 675:10.1021/ja01596a015 622: 602: 572: 552: 539: 496: 483: 459: 443: 430: 316: 296: 275: 262: 236: 183: 163: 126: 624: 610: 582: 560: 527: 522: 498: 471: 466: 447: 418: 413: 355: 321: 304: 276: 263: 250: 216: 188: 171: 143: 106: 807:Collected Volumes 795:Organic Syntheses 775:10.1021/jo025792p 669:(15): 3613–3614. 613: 589: 581: 575: 563: 530: 521: 474: 465: 450: 421: 412: 406: 351:organic synthesis 319: 307: 283: 266: 253: 246: 223: 215: 186: 174: 150: 142: 136: 113: 105: 32:organic chemistry 16:(Redirected from 834: 812: 810: 803: 785: 779: 778: 762: 756: 741: 735: 734: 732:Internet Archive 730:– via the 719: 709: 703: 702: 685: 679: 678: 663:J. Am. Chem. Soc 658: 643:Suzuki couplings 633: 631: 630: 625: 623: 621: 618: 611: 601: 598: 593: 587: 579: 573: 571: 568: 561: 551: 548: 543: 538: 535: 528: 519: 507: 505: 504: 499: 497: 495: 492: 487: 482: 479: 472: 463: 458: 455: 448: 442: 439: 434: 429: 426: 419: 410: 404: 388: 376:Trimethyl borate 347:Trimethyl borate 330: 328: 327: 322: 320: 317: 315: 312: 305: 295: 292: 287: 281: 274: 271: 264: 261: 258: 251: 244: 235: 232: 227: 221: 213: 197: 195: 194: 189: 187: 184: 182: 179: 172: 162: 159: 154: 148: 140: 134: 125: 122: 117: 111: 103: 87: 68: 21: 842: 841: 837: 836: 835: 833: 832: 831: 817: 816: 815: 805: 787: 786: 782: 764: 763: 759: 742: 738: 728: 711: 710: 706: 700: 687: 686: 682: 660: 659: 655: 651: 513: 512: 398: 397: 387: 383: 379: 203: 202: 97: 96: 86: 82: 78: 74: 67: 63: 28: 23: 22: 15: 12: 11: 5: 840: 838: 830: 829: 819: 818: 814: 813: 780: 757: 736: 726: 704: 698: 680: 652: 650: 647: 635: 634: 617: 608: 605: 597: 592: 586: 578: 567: 558: 555: 547: 542: 534: 526: 509: 508: 491: 486: 478: 470: 462: 454: 446: 438: 433: 425: 417: 409: 391:boronic esters 332: 331: 311: 302: 299: 291: 286: 280: 270: 257: 249: 242: 239: 231: 226: 220: 211: 199: 198: 178: 169: 166: 158: 153: 147: 139: 132: 129: 121: 116: 110: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 839: 828: 827:Borate esters 825: 824: 822: 808: 801: 797: 796: 791: 784: 781: 776: 772: 768: 761: 758: 755: 752:, 4629–4631. 751: 747: 740: 737: 733: 729: 727:0-582-44367-9 723: 718: 717: 708: 705: 701: 699:0-582-22628-7 695: 691: 684: 681: 676: 672: 668: 664: 657: 654: 648: 646: 644: 640: 639:boronic acids 615: 606: 603: 595: 565: 556: 553: 545: 532: 511: 510: 489: 476: 460: 452: 436: 423: 407: 396: 395: 394: 392: 377: 373: 371: 367: 366:Lewis acidity 362: 360: 352: 348: 344: 340: 337: 336:sulfuric acid 309: 300: 297: 289: 268: 255: 240: 237: 229: 209: 201: 200: 176: 167: 164: 156: 130: 127: 119: 95: 94: 93: 91: 72: 61: 57: 53: 49: 45: 41: 37: 36:borate esters 33: 19: 806: 799: 793: 783: 767:J. Org. Chem 766: 760: 749: 745: 739: 715: 707: 689: 683: 666: 662: 656: 636: 374: 363: 356: 333: 60:orthoborates 35: 29: 18:Borate ester 71:metaborates 649:References 48:boric acid 577:⟶ 445:⟶ 248:⟶ 138:⟶ 821:Category 746:Polymer, 90:boroxine 52:alcohols 449:MgBrOCH 92:rings. 748:1996, 724:  696:  405:ArMgBr 56:esters 380:B(OCH 359:diols 64:B(OR) 50:with 802:: 90 722:ISBN 694:ISBN 612:HOCH 83:(OR) 69:and 38:are 771:doi 671:doi 580:ArB 529:OCH 520:ArB 473:OCH 464:ArB 420:OCH 245:ROH 135:ROH 46:of 30:In 823:: 804:; 800:49 798:. 792:. 750:37 667:78 665:. 645:. 588:OH 378:, 282:OR 222:OH 149:OR 112:OH 73:, 62:, 58:: 34:, 811:. 777:. 773:: 677:. 673:: 616:3 607:2 604:+ 596:2 591:) 585:( 574:O 566:2 562:H 557:2 554:+ 546:2 541:) 533:3 525:( 490:2 485:) 477:3 469:( 461:+ 453:3 437:3 432:) 424:3 416:( 411:B 408:+ 386:3 384:) 382:3 353:. 318:O 310:2 306:H 301:6 298:+ 290:3 285:) 279:( 269:3 265:O 256:3 252:B 241:3 238:+ 230:3 225:) 219:( 214:B 210:3 185:O 177:2 173:H 168:3 165:+ 157:3 152:) 146:( 141:B 131:3 128:+ 120:3 115:) 109:( 104:B 85:3 81:3 79:O 77:3 75:B 66:3 20:)

Index

Borate ester
organic chemistry
organoboron compounds
condensation reaction
boric acid
alcohols
esters
orthoborates
metaborates
boroxine
sulfuric acid

Trimethyl borate
organic synthesis
diols
Lewis acidity
Gutmann-Beckett method
Trimethyl borate
boronic esters
boronic acids
Suzuki couplings
doi
10.1021/ja01596a015
ISBN
0-582-22628-7
Vogel's Textbook of Macro and Semimicro Qualitative Inorganic Analysis
ISBN
0-582-44367-9
Internet Archive
doi: 10.1016/0032-3861(96)00323-0

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