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Dimethylacetamide

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Iloukhani, H., K. Khanlarzadeh. "Densities, viscosities, and refractive indices for binary and ternary mixtures of N, N-dimethylacetamide (1)+ 2-methylbutan-2-ol (2)+ ethyl acetate (3) at 298.15 K for m liquid region and at ambient pressure". Journal of Chemical & Engineering Data, 51.4 (2006):
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FDA warns health care professionals not to use Treanda Injection (solution) with closed system transfer devices, adapters, and syringes containing polycarbonate or acrylonitrile-butadiene-styrene
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Agreement of the Member State Committee on the Identification of N,N-Dimethylacetamide (DMAC) as a Substance of Very High Concern – Adopted on 24 November 2011
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Weiss, A. J.; Mancall, E. L.; Koltes, J. A.; White, J. C.; Jackson, L. G. (1962). "Dimethylacetamide: A Hitherto Unrecognized Hallucinogenic Agent".
1546: 776: 1911: 369: 1927: 1246:. Unlike many other cellulose solvents, LiCl/DMAc gives a molecular dispersion, i.e. a "true solution". For this reason, it is used in 1439:
Munro, D. D.; Stoughton, R. B. (1965). "Dimethylacetamide (DMAC) and Dimethylformamide (DMFA). Effect on Percutaneous Absorption".
1125: 32: 1328:. In 2014, the European Commission has started an investigation to restrict the use of dimethylacetamide in the EU according to 613: 983: 586: 1797:
Weiss, A. J.; Jackson, L. G.; Carabasi, R. A.; Mancall, E. L.; White, J. C. (1962). "A Phase I Study of Dimethylacetamide".
516: 1312:. Devices (e.g. syringes) that contain polycarbonate or ABS can dissolve when coming into contact with dimethylacetamide. 1208:
However, it is resistant to bases. For this reason DMA is a useful solvent for reactions involving strong bases such as
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Commission des normes, de l'équité, de la santé et de la sécurité du travail (CNESST), Quebec, Canada:
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Dimethylacetamide, like most simple alkyl amides, is of low acute toxicity. Chronic exposure can cause
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Grafmans, Horst; Maas, Steffen; Weck, Alexander; Rütter, Heinz; Schulz, Michael; Ross, Karl-Heinz.
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Process flowsheet of Dimethylacetamide Production from Acetic Acid and Dimethylamine
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U.S. Department of Health and Human Services & U.S. Department of Labor (1978)
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In 2015, the CNESST (Committee on Standards, Equity, Health and Safety at Work in
1038:. This colorless, water-miscible, high-boiling liquid is commonly used as a polar 260: 1845: 1228: 812: 1610: 1282: 1117: 966: 506: 1932: 1498: 866: 836: 1941: 1662:
Baum, S. L.; Suruda, A. J. (1997). "Toxic Hepatitis from Dimethylacetamide".
1519: 1305: 1294: 1113: 1062: 1046:. DMA is miscible with most other solvents, although it is poorly soluble in 567: 471: 461: 195: 1764: 1714: 1136:
in rectification columns. DMA is obtained with essentially quantitive (99%)
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The separation and purification of the product is carried out by multistage
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May cause damage to organs through prolonged or repeated exposure (H373)
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Lee, C.-Y.; Jung, S.-J.; Kim, S.-A.; Park, K.-S.; Ha, B.-G. (2006).
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Except where otherwise noted, data are given for materials in their
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Specific target organ toxicity – single exposure – narcotic effects
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Dimethylacetamide is commonly used as a solvent for fibers (e.g.,
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International Journal of Occupational and Environmental Health
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Immediately Dangerous to Life or Health Concentrations (IDLH)
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Suspected of damaging fertility or the unborn child (H361)
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The chemical reactions of dimethylacetamide are typical of
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Dimethylacetamide can also be produced by the reaction of
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Cheung, H.; Tanke, R. S.; Torrence, G. P. "Acetic Acid".
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In 2011, dimethylacetamide was identified in the EU as a
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National Institute for Occupational Safety and Health
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National Institute for Occupational Safety and Health
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Occupational Health Guideline for Dimethyl Acetamide
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It is also employed in the production of 1912:WHMIS 2015 classification of N,N-Dimethylacetamide 1581: 1369:Specific target organ toxicity – repeated exposure 1939: 1061:DMA is prepared commercially by the reaction of 705: 259: 1608: 750: 79: 1547:Ullmann's Encyclopedia of Industrial Chemistry 1164:of the acyl-N bond occurs in the presence of 1143: 1933:CDC – NIOSH Pocket Guide to Chemical Hazards 1577: 1575: 1304:Dimethylacetamide may be incompatible with 1056: 476:165.1 °C; 329.1 °F; 438.2 K 1124: 328: 205: 183: 1773: 1763: 1722: 1640: 1638: 1572: 1539: 1537: 1408:May cause drowsiness or dizziness (H336) 295: 1497:NIOSH Pocket Guide to Chemical Hazards. 1703:Occupational and Environmental Medicine 324: 237: 1940: 1899:Commission Regulation (EU) No 895/2014 1650:DHHS (NIOSH) Publication Number 81-123 1635: 1534: 1514: 1512: 1492: 1490: 1488: 807:490 °C (914 °F; 763 K) 196: 1386:Causes serious eye irritation (H319) 1257:Dimethylacetamide is also used as an 793:63 °C (145 °F; 336 K) 466:−20 °C (−4 °F; 253 K) 356:Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N 163: 143: 1453:10.1001/archderm.1965.01600170101020 1746:Gong, W.; Liu, X.; Zhu, B. (2016). 1509: 1485: 353:InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 250: 13: 746: 14: 1964: 1921: 1380:Serious eye damage/eye irritation 1242:in DMAc (LiCl/DMAc) can dissolve 973: 667: 662: 410: 404: 31: 22: 1904: 1892: 1880: 1868: 1817: 1790: 1739: 1690: 969:(at 25 °C , 100 kPa). 1655: 1602: 1467: 1432: 1322:Substance of very high concern 413: 398: 1: 1556:10.1002/14356007.a01_045.pub2 1425: 1315: 1248:gel permeation chromatography 887:(US health exposure limits): 855:4.62 g/kg (oral, mouse) 1846:10.1126/science.136.3511.151 1140:referred to methyl acetate. 7: 1799:Cancer Chemotherapy Reports 1752:Journal of Thoracic Disease 1391:Acute toxicity – inhalation 1276: 913:TWA 10 ppm (35 mg/m) 900:TWA 10 ppm (35 mg/m) 825:or concentration (LD, LC): 10: 1969: 1805:(February 1962): 477–485. 1630:, vol. 6, p. 503 1609:Zen, S.; Kaji, E. (1977). 1419:Combustible liquid (H227) 1144:Reactions and applications 1611:"Dimethyl nitrosuccinate" 1261:in drugs, e.g. in Vumon ( 963: 930: 881: 853:4.8 g/kg (oral, rat) 821: 643: 638: 560: 385: 365: 340: 63: 44: 39: 30: 21: 1397:Toxic if inhaled (H331) 1057:Synthesis and production 718:Precautionary statements 1765:10.21037/jtd.2016.04.44 1715:10.1136/oem.2005.023580 1550:. Weinheim: Wiley-VCH. 1441:Archives of Dermatology 1252:molar mass distribution 1235:as a reaction medium. 634:−2.5835–−2.5805 MJ/mol 1676:10.1179/oeh.1997.3.1.1 1324:(SVHC) because of its 1287:central nervous system 1254:of cellulose samples. 873:2475 ppm (rat, 1  757: 1358:Reproductive toxicity 1326:reproductive toxicity 756: 1520:"Dimethyl acetamide" 1352:GHS hazard statement 867:median concentration 739:(fire diamond) 46:Preferred IUPAC name 1838:1962Sci...136..151W 483:Solubility in water 428: g·mol 125:Beilstein Reference 18: 996:Infobox references 931:Related compounds 922:(Immediate danger) 758: 57:-Dimethylacetamide 17:Dimethylacetamide 16: 1832:(3511): 151–152. 1628:Collected Volumes 1616:Organic Syntheses 1480:10.1021/je050538q 1423: 1422: 1250:to determine the 1217:polyacrylonitrile 1044:organic synthesis 1008:Dimethylacetamide 1004:Chemical compound 1002: 1001: 955:methylpyrrolidone 945:dimethylformamide 937:Related compounds 851: 846: 692:Hazard statements 436:Colorless liquid 309:CompTox Dashboard 239:dimethylacetamide 105:Interactive image 1960: 1915: 1908: 1902: 1896: 1890: 1884: 1878: 1877:. 10 March 2015. 1872: 1866: 1865: 1821: 1815: 1814: 1794: 1788: 1787: 1777: 1767: 1758:(6): E408–E411. 1743: 1737: 1736: 1726: 1694: 1688: 1687: 1659: 1653: 1642: 1633: 1631: 1624: 1606: 1600: 1599: 1597: 1595: 1579: 1570: 1569: 1541: 1532: 1531: 1516: 1507: 1506: 1494: 1483: 1471: 1465: 1464: 1436: 1413:Flammable liquid 1342: 1341: 1240:lithium chloride 1210:sodium hydroxide 1128: 1067:acetic anhydride 1020:organic compound 986: 980: 977: 976: 849: 845:(dermal, rabbit) 844: 813:Explosive limits 778: 771: 764: 749: 729: 725: 711: 707: 703: 699: 671: 666: 630: 603: 580:178.2 J/(K·mol) 576: 561:Thermochemistry 533:Refractive index 427: 415: 412: 406: 400: 393:Chemical formula 333: 332: 317: 315: 299: 263: 252: 241: 217: 209: 198: 187: 167: 147: 118:DMA, DMAC, DMAc 107: 83: 35: 26: 19: 15: 1968: 1967: 1963: 1962: 1961: 1959: 1958: 1957: 1938: 1937: 1924: 1919: 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1935: 1930: 1923: 1922:External links 1920: 1917: 1916: 1903: 1891: 1879: 1867: 1816: 1789: 1738: 1689: 1654: 1634: 1601: 1588:Google Patents 1571: 1565:978-3527306732 1564: 1533: 1508: 1484: 1466: 1447:(5): 585–586. 1430: 1429: 1427: 1424: 1421: 1420: 1417: 1414: 1410: 1409: 1406: 1403: 1399: 1398: 1395: 1392: 1388: 1387: 1384: 1381: 1377: 1376: 1373: 1370: 1366: 1365: 1362: 1359: 1355: 1354: 1349: 1346: 1317: 1314: 1295:hallucinations 1283:hepatotoxicity 1278: 1275: 1238:A solution of 1206: 1205: 1201: 1197: 1193: 1189: 1185: 1181: 1177: 1173: 1145: 1142: 1130: 1129: 1118:methyl acetate 1110: 1109: 1106: 1102: 1098: 1094: 1090: 1086: 1082: 1078: 1058: 1055: 1035: 1031: 1027: 1003: 1000: 999: 994: 972: 971: 967:standard state 964: 961: 960: 958: 957: 952: 947: 941: 939: 936: 933: 932: 928: 927: 924: 918: 915: 914: 911: 905: 902: 901: 898: 892: 889: 888: 879: 878: 871: 862: 860: 857: 856: 848:4.3 g/kg 841: 832: 830: 827: 826: 819: 818: 815: 809: 808: 805: 798: 795: 794: 791: 785: 784: 774: 767: 760: 745: 744: 743: 742: 740: 731: 730: 721: 716: 713: 712: 695: 690: 687: 686: 681: 676: 673: 672: 660: 655: 652: 651: 641: 640: 636: 635: 632: 626: 620: 612: 609: 608: 607:−300.1 kJ/mol 605: 599: 593: 585: 582: 581: 578: 566: 563: 562: 558: 557: 554: 548: 547: 544: 539: 531: 528: 527: 524: 520: 513: 512: 509: 507:Vapor pressure 503: 502: 499: 490: 489: 486: 481: 478: 477: 474: 468: 467: 464: 458: 457: 454: 448: 447: 444: 438: 437: 434: 430: 429: 423: 417: 416: 407: 401: 396: 391: 388: 387: 383: 382: 380: 379: 376: 368: 367: 366: 363: 362: 360: 359: 355: 352: 351: 343: 342: 341: 338: 337: 335: 334: 321: 319: 307: 304: 303: 301: 300: 292: 290: 284: 283: 281: 280: 276: 274: 268: 267: 265: 264: 256: 254: 246: 243: 242: 235: 229: 228: 226: 225: 221: 219: 211: 210: 200: 192: 191: 189: 188: 180: 178: 172: 171: 169: 168: 160: 158: 152: 151: 149: 148: 140: 138: 132: 131: 128: 123: 120: 119: 116: 115:Abbreviations 112: 111: 109: 108: 100: 98: 91: 88: 87: 85: 84: 76: 74: 69: 66: 65: 61: 60: 49: 48: 42: 41: 37: 36: 28: 27: 9: 6: 4: 3: 2: 1965: 1954: 1951: 1949: 1946: 1945: 1943: 1934: 1931: 1929: 1926: 1925: 1913: 1907: 1900: 1895: 1888: 1883: 1876: 1871: 1863: 1859: 1855: 1851: 1847: 1843: 1839: 1835: 1831: 1827: 1820: 1812: 1808: 1804: 1800: 1793: 1785: 1781: 1776: 1771: 1766: 1761: 1757: 1753: 1749: 1742: 1734: 1730: 1725: 1720: 1716: 1712: 1708: 1704: 1700: 1693: 1685: 1681: 1677: 1673: 1669: 1665: 1658: 1651: 1647: 1641: 1639: 1629: 1622: 1618: 1617: 1612: 1605: 1589: 1585: 1578: 1576: 1567: 1561: 1557: 1553: 1549: 1548: 1540: 1538: 1529: 1525: 1521: 1515: 1513: 1504: 1500: 1493: 1491: 1489: 1481: 1477: 1470: 1462: 1458: 1454: 1450: 1446: 1442: 1435: 1431: 1418: 1415: 1412: 1411: 1407: 1404: 1401: 1400: 1396: 1393: 1390: 1389: 1385: 1382: 1379: 1378: 1374: 1371: 1368: 1367: 1363: 1360: 1357: 1356: 1353: 1350: 1347: 1344: 1343: 1340: 1338: 1333: 1331: 1327: 1323: 1313: 1311: 1307: 1306:polycarbonate 1302: 1300: 1296: 1292: 1288: 1284: 1274: 1272: 1268: 1265:), Busulfex ( 1264: 1260: 1255: 1253: 1249: 1245: 1241: 1236: 1234: 1230: 1226: 1222: 1218: 1213: 1211: 1188:O + HCl → CH 1171: 1170: 1169: 1167: 1163: 1159: 1155: 1151: 1141: 1139: 1135: 1127: 1123: 1122: 1121: 1119: 1115: 1114:dimethylamine 1076: 1075: 1074: 1072: 1068: 1064: 1063:dimethylamine 1054: 1052: 1049: 1045: 1041: 1025: 1021: 1017: 1013: 1009: 997: 990: 985: 968: 962: 956: 953: 951: 948: 946: 943: 942: 940: 935: 934: 929: 925: 921: 917: 916: 912: 909:(Recommended) 908: 904: 903: 899: 896:(Permissible) 895: 891: 890: 886: 885: 880: 876: 872: 868: 859: 858: 842: 838: 829: 828: 824: 820: 816: 814: 811: 810: 806: 803: 797: 796: 792: 790: 787: 786: 779: 772: 765: 741: 738: 737: 733: 732: 722: 719: 715: 714: 696: 693: 689: 688: 685: 682: 679: 675: 674: 670: 665: 661: 658: 654: 653: 649: 647: 642: 637: 633: 625: 617: 611: 610: 606: 598: 590: 584: 583: 579: 574: 569: 568:Heat capacity 565: 564: 559: 556:0.945 mPa·s 555: 553: 550: 549: 545: 538: 534: 530: 529: 525: 518: 515: 514: 510: 508: 505: 504: 500: 498: 497: 492: 491: 487: 484: 480: 479: 475: 473: 472:Boiling point 470: 469: 465: 463: 462:Melting point 460: 459: 455: 453: 450: 449: 445: 443: 440: 439: 435: 432: 431: 424: 422: 419: 418: 397: 394: 390: 389: 384: 375: 374: 371: 364: 350: 349: 346: 339: 331: 327: 326:DTXSID5020499 323: 322: 320: 310: 306: 305: 298: 294: 293: 291: 289: 286: 285: 278: 277: 275: 273: 270: 269: 262: 258: 257: 255: 249: 245: 244: 240: 236: 234: 231: 230: 223: 222: 220: 218: 213: 212: 208: 204: 201: 199: 197:ECHA InfoCard 194: 193: 186: 182: 181: 179: 177: 174: 173: 166: 162: 161: 159: 157: 154: 153: 146: 142: 141: 139: 137: 134: 133: 129: 126: 122: 121: 117: 114: 113: 106: 102: 101: 99: 95: 90: 89: 82: 78: 77: 75: 72: 68: 67: 62: 56: 52: 47: 43: 38: 34: 29: 25: 20: 1906: 1894: 1882: 1870: 1829: 1825: 1819: 1802: 1798: 1792: 1755: 1751: 1741: 1706: 1702: 1692: 1667: 1663: 1657: 1627: 1620: 1614: 1604: 1592:. Retrieved 1587: 1545: 1523: 1469: 1444: 1440: 1434: 1334: 1319: 1303: 1280: 1256: 1237: 1233:plasticizers 1223:) or in the 1214: 1207: 1153: 1149: 1147: 1134:distillation 1131: 1111: 1060: 1051:hydrocarbons 1015: 1011: 1007: 1006: 883: 822: 800:Autoignition 735: 683: 645: 623: 596: 572: 536: 495: 272:RTECS number 64:Identifiers 54: 50: 1474:1226–1231. 1345:Description 1071:acetic acid 850:(oral, rat) 837:median dose 823:Lethal dose 802:temperature 789:Flash point 678:Signal word 456:0.937 g/mL 446:Ammoniacal 433:Appearance 386:Properties 377:CN(C)C(C)=O 203:100.004.389 165:ChEMBL11873 145:CHEBI:84254 1953:Acetamides 1942:Categories 1670:(1): 1–4. 1426:References 1316:Regulation 1291:depression 1263:teniposide 1192:COOH + (CH 1162:Hydrolysis 817:1.8–11.5% 657:Pictograms 616:combustion 421:Molar mass 297:JCV5VDB3HY 176:ChemSpider 92:3D model ( 71:CAS Number 1590:. BASF SE 1271:amsacrine 1259:excipient 1244:cellulose 1048:aliphatic 1022:with the 1018:) is the 950:acetamide 728:P308+P313 648:labelling 589:formation 552:Viscosity 488:Miscible 279:AB7700000 224:204-826-4 216:EC Number 1862:20098340 1854:14005854 1811:14005853 1784:27293868 1733:16728503 1530:(NIOSH). 1505:(NIOSH). 1348:Category 1299:delusion 1277:Toxicity 1267:busulfan 1225:adhesive 1030:C(O)N(CH 926:300 ppm 736:NFPA 704 639:Hazards 130:1737614 81:127-19-5 1834:Bibcode 1826:Science 1775:4885965 1724:2078052 1684:9891094 1594:18 July 1499:"#0218" 1461:5844405 1221:spandex 1085:H·HN(CH 1040:solvent 1024:formula 989:what is 987: ( 546:1.4375 526:270 nm 511:300 Pa 501:−0.253 452:Density 248:PubChem 1860:  1852:  1809:  1782:  1772:  1731:  1721:  1682:  1562:  1459:  1337:Quebec 1289:(e.g. 1176:CON(CH 1158:amides 1101:CON(CH 1097:O + CH 984:verify 981:  684:Danger 517:UV-vis 426:87.122 370:SMILES 156:ChEMBL 40:Names 1858:S2CID 1330:REACH 1166:acids 1138:yield 1116:with 1065:with 884:NIOSH 345:InChI 261:31374 185:29107 136:ChEBI 94:JSmol 1850:PMID 1807:PMID 1780:PMID 1729:PMID 1680:PMID 1623:: 60 1596:2019 1560:ISBN 1457:PMID 1297:and 1231:and 1012:DMAc 920:IDLH 724:P280 710:H360 706:H332 702:H319 698:H312 494:log 442:Odor 288:UNII 233:MeSH 1842:doi 1830:136 1770:PMC 1760:doi 1719:PMC 1711:doi 1672:doi 1552:doi 1476:doi 1449:doi 1310:ABS 1308:or 1301:). 1273:). 1184:+ H 1093:→ H 1069:or 1042:in 1016:DMA 1014:or 907:REL 894:PEL 646:GHS 627:298 600:298 521:max 314:EPA 251:CID 1944:: 1856:. 1848:. 1840:. 1828:. 1803:16 1801:. 1778:. 1768:. 1754:. 1750:. 1727:. 1717:. 1707:63 1705:. 1701:. 1678:. 1666:. 1637:^ 1625:; 1621:57 1619:. 1613:. 1586:. 1574:^ 1558:. 1536:^ 1526:. 1522:. 1511:^ 1501:. 1487:^ 1455:. 1445:92 1443:. 1332:. 1293:, 1219:, 1212:. 1204:Cl 1200:NH 1172:CH 1168:: 1160:. 1120:. 1081:CO 1077:CH 1053:. 1026:CH 877:) 863:50 861:LC 833:50 831:LD 726:, 708:, 704:, 700:, 650:: 619:(Δ 592:(Δ 523:) 519:(λ 1914:. 1889:. 1864:. 1844:: 1836:: 1813:. 1786:. 1762:: 1756:8 1735:. 1713:: 1686:. 1674:: 1668:3 1632:. 1598:. 1568:. 1554:: 1482:. 1478:: 1463:. 1451:: 1416:4 1405:3 1394:3 1383:2 1372:2 1361:2 1202:2 1198:2 1196:) 1194:3 1190:3 1186:2 1182:2 1180:) 1178:3 1174:3 1154:N 1152:, 1150:N 1107:2 1105:) 1103:3 1099:3 1095:2 1091:2 1089:) 1087:3 1083:2 1079:3 1036:2 1034:) 1032:3 1028:3 1010:( 979:N 875:h 869:) 865:( 839:) 835:( 777:0 770:2 763:2 629:) 624:H 621:c 602:) 597:H 594:f 575:) 573:C 571:( 542:) 540:D 537:n 535:( 496:P 414:O 411:N 408:9 405:H 402:4 399:C 316:) 312:( 96:) 55:N 53:, 51:N

Index

Skeletal formula of dimethylacetamide
Ball and stick model of dimethylacetamide
Preferred IUPAC name
CAS Number
127-19-5
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:84254
ChEMBL
ChEMBL11873
ChemSpider
29107
ECHA InfoCard
100.004.389
Edit this at Wikidata
EC Number
MeSH
dimethylacetamide
PubChem
31374
RTECS number
UNII
JCV5VDB3HY
CompTox Dashboard
DTXSID5020499
Edit this at Wikidata
InChI
SMILES

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