Knowledge (XXG)

Mosher's acid

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J. A. Dale; H. S. Mosher (1973). "Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters".
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J. A. Dale; D. L. Dull; H. S. Mosher (1969). "α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines".
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D. L. Dull; H. S. Mosher (1967). "Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids".
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D. E. Ward; C. K. Rhee (1991). "A simple method for the microscale preparation of Mosher's acid chloride".
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Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L.
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Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines
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InChI=1S/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)
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InChI=1/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)
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Y. Goldberg; H. Alper (1992). "A new and simple synthesis of Mosher's acid".
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105 to 107 °C (221 to 225 °F; 378 to 380 K) at 1 torr
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Except where otherwise noted, data are given for materials in their
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form, is sometimes used because it has better reactivity.
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of the ester or amide is then determined by proton and/or
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46 to 49 °C (115 to 120 °F; 319 to 322 K)
688: 755:As a chiral derivatizing agent, it reacts with an 289: 277: 155: 143: 131: 109:Methoxy(trifluoromethyl)phenylacetic acid, MTPA 8: 717:α-methoxy-α-trifluoromethylphenylacetic acid 221: 199: 15: 334: 322: 310: 908:Journal of the American Chemical Society 850:Journal of the American Chemical Society 809: 418: 383: 363: 644:110 °C (230 °F; 383 K) 212: 390:Key: JJYKJUXBWFATTE-UHFFFAOYSA-N 7: 400:Key: JJYKJUXBWFATTE-UHFFFAOYAJ 263: 14: 678: 524: 767:to form an ester or amide. The 674:(at 25 °C , 100 kPa). 101:methoxy-2-phenylpropanoic acid 93:methoxy-2-phenylpropanoic acid 1: 421:COC(C(O)=O)(c1ccccc1)C(F)(F)F 973:10.1016/0040-4039(91)80466-J 879:Journal of Organic Chemistry 820:Journal of Organic Chemistry 50: 22: 1024: 1003:Trifluoromethyl compounds 733:chiral derivatizing agent 668: 648: 505: 500: 429: 409: 374: 114: 106: 82: 77: 49: 21: 739:molecule, consisting of 727:which was first used by 571:Precautionary statements 782:Mosher's acid chloride 769:absolute configuration 663:Mosher's acid chloride 68: 59: 40: 31: 67: 58: 39: 30: 468:234.17 99:)-3,3,3-trifluoro-2- 91:)-3,3,3-trifluoro-2- 960:Tetrahedron Letters 921:10.1021/ja00992a053 892:10.1021/jo00039a043 863:10.1021/ja00783a034 833:10.1021/jo01261a013 18: 729:Harry Stone Mosher 701:Infobox references 649:Related compounds 69: 60: 41: 32: 16: 967:(49): 7165–7166. 933:See for example: 886:(13): 3731–3732. 709:Chemical compound 707: 706: 549:Hazard statements 348:CompTox Dashboard 251:): 241-292-1 244:): 243-829-5 181:Interactive image 73: 72: 45: 44: 1015: 1008:Phenyl compounds 998:Carboxylic acids 977: 976: 954: 948: 931: 925: 924: 902: 896: 895: 873: 867: 866: 843: 837: 836: 827:(9): 2543–2549. 814: 798:Pirkle's alcohol 776:NMR spectroscopy 691: 685: 682: 681: 634: 630: 626: 622: 618: 614: 610: 606: 602: 598: 594: 590: 586: 582: 578: 564: 560: 556: 528: 437:Chemical formula 367: 356: 354: 338: 326: 314: 309:(racemic): 293: 281: 265: 233: 225: 214: 203: 183: 159: 147: 135: 130:(racemic): 100: 92: 51: 23: 19: 1023: 1022: 1018: 1017: 1016: 1014: 1013: 1012: 993:Stereochemistry 983: 982: 981: 980: 956: 955: 951: 932: 928: 904: 903: 899: 875: 874: 870: 845: 844: 840: 816: 815: 811: 806: 794: 765:stereochemistry 753: 725:carboxylic acid 710: 703: 698: 697: 696:  ?) 687: 683: 679: 675: 659: 573: 551: 537: 521: 457: 453: 449: 445: 439: 425: 422: 417: 416: 405: 402: 401: 398: 392: 391: 388: 382: 381: 370: 357: 350: 341: 296: 266: 254: 206: 186: 173: 162: 124: 110: 102: 94: 12: 11: 5: 1021: 1019: 1011: 1010: 1005: 1000: 995: 985: 984: 979: 978: 949: 939:J. Chem. Educ. 926: 897: 868: 857:(2): 512–519. 838: 808: 807: 805: 802: 801: 800: 793: 790: 752: 749: 708: 705: 704: 699: 677: 676: 672:standard state 669: 666: 665: 660: 654: 651: 650: 646: 645: 642: 636: 635: 601:P305+P351+P338 574: 569: 566: 565: 552: 547: 544: 543: 538: 533: 530: 529: 522: 517: 514: 513: 503: 502: 498: 497: 494: 488: 487: 484: 478: 477: 474: 470: 469: 466: 460: 459: 455: 451: 447: 443: 440: 435: 432: 431: 427: 426: 424: 423: 420: 412: 411: 410: 407: 406: 404: 403: 399: 396: 395: 393: 389: 386: 385: 377: 376: 375: 372: 371: 369: 368: 365:DTXSID90897007 360: 358: 346: 343: 342: 340: 339: 327: 315: 306: 304: 298: 297: 295: 294: 282: 269: 267: 259: 256: 255: 253: 252: 245: 237: 235: 227: 226: 216: 208: 207: 205: 204: 196: 194: 188: 187: 185: 184: 176: 174: 167: 164: 163: 161: 160: 148: 136: 127: 125: 120: 117: 116: 112: 111: 108: 104: 103: 86: 80: 79: 75: 74: 71: 70: 61: 47: 46: 43: 42: 33: 17:Mosher's acid 13: 10: 9: 6: 4: 3: 2: 1020: 1009: 1006: 1004: 1001: 999: 996: 994: 991: 990: 988: 974: 970: 966: 962: 961: 953: 950: 947: 943: 940: 936: 930: 927: 922: 918: 914: 910: 909: 901: 898: 893: 889: 885: 881: 880: 872: 869: 864: 860: 856: 852: 851: 842: 839: 834: 830: 826: 822: 821: 813: 810: 803: 799: 796: 795: 791: 789: 787: 786:acid chloride 783: 779: 777: 774: 770: 766: 762: 758: 750: 748: 747:enantiomers. 746: 742: 738: 734: 730: 726: 722: 718: 714: 713:Mosher's acid 702: 695: 690: 673: 667: 664: 661: 658: 657:acyl chloride 653: 652: 647: 643: 641: 638: 637: 575: 572: 568: 567: 553: 550: 546: 545: 542: 539: 536: 532: 531: 527: 523: 520: 516: 515: 511: 509: 504: 499: 495: 493: 492:Boiling point 490: 489: 485: 483: 482:Melting point 480: 479: 475: 472: 471: 467: 465: 462: 461: 441: 438: 434: 433: 428: 419: 415: 408: 394: 384: 380: 373: 366: 362: 361: 359: 349: 345: 344: 337: 332: 328: 325: 320: 316: 313: 308: 307: 305: 303: 300: 299: 292: 287: 283: 280: 275: 271: 270: 268: 262: 258: 257: 250: 246: 243: 239: 238: 236: 234: 229: 228: 224: 220: 217: 215: 213:ECHA InfoCard 210: 209: 202: 198: 197: 195: 193: 190: 189: 182: 178: 177: 175: 171: 166: 165: 158: 153: 149: 146: 141: 137: 134: 129: 128: 126: 123: 119: 118: 113: 105: 98: 90: 85: 81: 76: 66: 62: 57: 53: 52: 48: 38: 34: 29: 25: 24: 20: 964: 958: 952: 941: 934: 929: 915:(16): 4230. 912: 906: 900: 883: 877: 871: 854: 848: 841: 824: 818: 812: 781: 780: 754: 751:Applications 744: 740: 720: 716: 712: 711: 540: 507: 330: 318: 285: 273: 248: 241: 151: 139: 115:Identifiers 107:Other names 96: 88: 944:, 85, 698. 763:of unknown 640:Flash point 535:Signal word 473:Appearance 430:Properties 219:100.153.604 84:IUPAC names 987:Categories 804:References 735:. It is a 519:Pictograms 464:Molar mass 336:172HCJ1IQV 324:27O5L9T1WM 312:E015GCC0MA 192:ChemSpider 168:3D model ( 157:17257-71-5 145:20445-31-2 133:81655-41-6 122:CAS Number 625:P403+P233 617:P337+P313 613:P332+P313 597:P304+P340 593:P302+P352 510:labelling 232:EC Number 946:Abstract 792:See also 655:Related 501:Hazards 333:): 321:): 288:): 276:): 154:): 142:): 757:alcohol 723:) is a 694:what is 692: ( 541:Warning 458: 291:6992788 279:2723917 261:PubChem 784:, the 737:chiral 689:verify 686:  476:solid 414:SMILES 78:Names 761:amine 731:as a 715:, or 379:InChI 201:78043 170:JSmol 942:2008 743:and 721:MTPA 633:P501 629:P405 621:P362 609:P321 605:P312 589:P280 585:P271 581:P264 577:P261 563:H335 559:H319 555:H315 302:UNII 969:doi 917:doi 888:doi 859:doi 829:doi 759:or 508:GHS 353:EPA 264:CID 989:: 965:32 963:. 913:89 911:. 884:57 882:. 855:95 853:. 825:34 823:. 778:. 631:, 627:, 623:, 619:, 615:, 611:, 607:, 603:, 599:, 595:, 591:, 587:, 583:, 579:, 561:, 557:, 512:: 444:10 975:. 971:: 923:. 919:: 894:. 890:: 865:. 861:: 835:. 831:: 773:F 745:S 741:R 719:( 684:N 456:3 454:O 452:3 450:F 448:9 446:H 442:C 355:) 351:( 331:S 329:( 319:R 317:( 286:S 284:( 274:R 272:( 249:S 247:( 242:R 240:( 172:) 152:S 150:( 140:R 138:( 97:S 95:( 89:R 87:(

Index





IUPAC names
CAS Number
81655-41-6
20445-31-2
17257-71-5
JSmol
Interactive image
ChemSpider
78043
ECHA InfoCard
100.153.604
Edit this at Wikidata
EC Number
PubChem
2723917
6992788
UNII
E015GCC0MA
27O5L9T1WM
172HCJ1IQV
CompTox Dashboard
DTXSID90897007
InChI
SMILES
Chemical formula
Molar mass

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