24:
430:
277:
1644:
47:
823:
818:
813:
914:
910:
37:
1432:
1216:
913:
1398:
915:
1688:
gas cannot be compressed and stored without the danger of explosion. Industrial acetylene is safely compressed in the presence of dimethylformamide, which forms a safe, concentrated solution. The casing is also filled with
2716:
Redlich, C.; Beckett, W. S.; Sparer, J.; Barwick, K. W.; Riely, C. A.; Miller, H.; Sigal, S. L.; Shalat, S. L.; Cullen, M. R. (1988). "Liver disease associated with occupational exposure to the solvent dimethylformamide".
2036:
IPCS (International
Programme on Chemical Safety) (1991). Environmental Health Criteria 114 "Dimethylformamide" United Nations Environment Programme, International Labour Organisation, World Health Organization;
1427:
is measured to −0.85. Since the density of DMF (0.95 g·cm at 20 °C) is similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.
931:
1408:
shows two methyl signals, indicative of hindered rotation about the (O)C−N bond. At temperatures near 100 °C, the 500 MHz NMR spectrum of this compound shows only one signal for the methyl groups.
831:
2383:
On p. 692, Verley states that DMF is prepared by a procedure analogous to that for the preparation of dimethylacetamide (see p. 691), which would be by distilling dimethylamine hydrochloride and
793:
1531:
DMF was first prepared in 1893 by the French chemist Albert Verley (8 January 1867 – 27 November 1959), by distilling a mixture of dimethylamine hydrochloride and potassium formate.
1775:. The density of the compound in the toy resulted in all squishies being removed from the Danish market. All squishies were recommended to be thrown out as household waste.
2691:
885:
916:
924:
23:
2765:
1918:
1893:
1090:
2047:
Taft, R. W.; Abraham, M. H.; Doherty, R. M.; Kamlet, M. J. (1985). "The molecular properties governing solubilities of organic nonelectrolytes in water".
2159:-Alkylamino-benzaldehyde" [On the reaction of phosphorus halides with alkyl formanilides. A new method for the preparation of secondary and tertiary
1229:
2155:; Haack, Albrecht (1927). "Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer
2004:
938:
1706:
469:
1960:
H. S. Gutowsky; C. H. Holm (1956). "Rate
Processes and Nuclear Magnetic Resonance Spectra. II. Hindered Internal Rotation of Amides".
1463:, which is used to formylate aromatic compounds. The process involves initial conversion of DMF to a chloroiminium ion, , known as a
2327:
Laurence, C. and Gal, J-F. Lewis
Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
1452:
near its boiling point to give dimethylamine. Distillation is therefore conducted under reduced pressure at lower temperatures.
2695:
762:
1716:
DMF can be utilized as a standard in proton NMR spectroscopy allowing for a quantitative determination of an unknown compound.
2754:
2525:
2433:
1842:
1224:
735:
2517:
638:
1416:
constant of 7.47 × 10 hPa·m/mol can be deduced from an experimentally determined equilibrium constant at 25 °C. The
2337:
Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases".
46:
2021:
2587:
2554:
2406:
2277:
2224:
2133:
1768:
444:
2207:. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry. Vol. 2.
1236:
36:
328:
1519:= 1.31. Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by
2602:
Ansell, M. F. in "The
Chemistry of Acyl Halides"; S. Patai, Ed.; John Wiley and Sons: London, 1972; pp 35–68.
1681:
It is used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.
1656:
2486:
2460:
1594:
1550:
1482:
1460:
875:
377:
272:
2370:
1383:, the spectroscopic evidence indicates partial double bond character for the C−N and C−O bonds. Thus, the
1935:
1802:
1387:
shows a C=O stretching frequency at only 1675 cm, whereas a ketone would absorb near 1700 cm.
408:
214:
1764:
Dimethylformamide vapor exposure has shown reduced alcohol tolerance and skin irritation in some cases.
881:
822:
2165:
1826:
1710:
1405:
1114:
1101:
817:
616:
284:
1823:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1598:
1565:
The primary use of DMF is as a solvent with low evaporation rate. DMF is used in the production of
961:
425:
322:
2792:
2240:
Jones, Gurnos; Stanforth, Stephen P. (2000). "The
Vilsmeier Reaction of Non-Aromatic Compounds".
1748:
1734:
1675:
144:
2579:
2572:
812:
162:
2355:
The plots shown in this paper used older parameters. Improved E&C parameters are listed in
1470:
1183:
2423:
2797:
2509:
1417:
1384:
985:
845:
805:
593:
2772:
2692:"Skumlegetøj afgiver farlige kemikalier (in English- Squishies giving dangerous chemicals)"
2546:
2302:
2200:
2117:
2058:
1969:
1328:
386:
66:
2613:
234:
8:
2787:
1339:
the samples under reduced pressure. As its name indicates, it is structurally related to
889:
110:
2306:
2062:
1973:
429:
276:
194:
120:
2667:
2642:
2216:
2074:
1444:
DMF is hydrolyzed by strong acids and bases, especially at elevated temperatures. With
1435:
Left: two resonance structures of DMF. Right: illustration highlighting delocalization.
1391:
1316:
174:
2734:
2672:
2583:
2550:
2521:
2429:
2402:
2384:
2273:
2220:
2129:
2017:
1838:
1464:
1456:
1300:
1296:
1152:
2078:
2046:
1643:
2726:
2662:
2654:
2346:
2310:
2250:
2212:
2174:
2121:
2066:
2049:
2009:
1977:
1830:
1702:
1636:
1632:
1624:
1574:
1474:
1445:
1308:
1256:
1252:
1160:
664:
582:
492:
2195:
Meth-Cohn, Otto; Stanforth, Stephen P. (1993). "The
Vilsmeier-Haack Reaction". In
2091:(BASF AG, department of analytical, unpublished data, J-No. 124659/08, 27.11.1987)
2013:
1869:
1755:
under microwave heating is a reagent for deuteration of polyaromatic hydrocarbons.
2715:
2482:
2463:[Methods of preparation of saturated aldehydes of the aliphatic series].
2456:
2152:
1727:
1720:
1660:
1628:
1543:
1449:
1412:
DMF is miscible with water. The vapour pressure at 20 °C is 3.5 hPa. A
1356:
1320:
974:
699:
350:
2730:
2461:"Modes de formation et de préparation des aldéhydes saturées de la série grasse"
2254:
1834:
2196:
1620:
1566:
1535:
1413:
1348:
1207:
1165:
606:
2761:
2514:
Name
Reactions: A Collection of Detailed Mechanisms and Synthetic Applications
1889:
1295:. Commonly abbreviated as DMF (although this initialism is sometimes used for
1078:
1056:
1011:
2781:
2178:
2125:
1671:
1609:
1539:
1360:
1324:
716:
571:
561:
265:
2773:
Concise
International Chemical Assessment Document 31: N,N-Dimethylformamide
1910:
1787:(oral, rats and mice) is 2.2–7.55 g/kg. Hazards of DMF have been examined.
1697:
As a cheap and common reagent, DMF has many uses in a research laboratory.
1616:
1344:
2738:
937:
2676:
2242:
1504:
1352:
1304:
950:
2658:
1719:
In the synthesis of organometallic compounds, it is used as a source of
923:
254:
2399:
Industrial
Organic Chemistry: Important Raw Materials and Intermediates
1578:
1336:
930:
653:
520:
285:
225:
2350:
2314:
1981:
867:
2621:
Publication 960-19 Measurement Issues in Single Wall Carbon Nanotubes
2356:
2101:
Comins, Daniel L.; Joseph, Sajan P. (2001). "N,N-Dimethylformamide".
2070:
1853:
and is the preferred IUPAC name. Substitution is permitted on the –NH
1772:
1690:
1685:
1602:
1582:
1554:
1520:
1508:
1340:
683:
397:
2487:"Nouvelle méthode générale synthétique de préparation des aldéhydes"
1206:
Except where otherwise noted, data are given for materials in their
2641:
Lyle, W. H.; Spence, T. W.; McKinneley, W. M.; Duckers, K. (1979).
2208:
1655:
and makes them swell. Because of this property DMF is suitable for
1652:
1570:
1478:
1269:
1260:
896:
311:
245:
2759:
2489:[Novel general synthetic method for preparing aldehydes].
1887:
143:
1667:
1586:
1489:
1431:
1363:. It facilitates reactions that follow polar mechanisms, such as
1312:
551:
337:
1323:
or degraded samples often have a fishy smell due to impurity of
2619:. In Freiman, S.; Hooker, S.; Migler; K.; Arepalli, S. (eds.).
1870:"Hazardous Substances Data Bank (HSDB) - N,N-DIMETHYLFORMAMIDE"
1500:
1493:
1284:
1266:
1263:
205:
2421:
1915:
Immediately Dangerous to Life or Health Concentrations (IDLH)
1635:. The catalytic mechanism entails reversible formation of an
1380:
1332:
361:
185:
133:
413:
2640:
1784:
1448:, DMF converts to formate and dimethylamine. DMF undergoes
1127:
1064:
859:
541:
302:
1577:
for pharmaceuticals, in the development and production of
1397:
855:
2396:
1549:
Although currently impractical, DMF can be prepared from
1364:
1327:. Dimethylamine degradation impurities can be removed by
1195:
851:
2336:
1959:
2292:
1849:
The traditional name 'formamide' is retained for HCO-NH
1733:
DMF is commonly used in the solvothermal synthesis of
2766:
National Institute for Occupational Safety and Health
1919:
National Institute for Occupational Safety and Health
1894:
National Institute for Occupational Safety and Health
1311:
and the majority of organic liquids. DMF is a common
1492:
with a variety of Lewis acids such as the soft acid
2611:
2373:[On the preparation of amides in general].
2293:Vogel G. C.; Drago, R. S. (1996). "The ECW Model".
2571:
2194:
2270:Comprehensive organic name reactions and reagents
1615:It is a common catalyst used in the synthesis of
161:
2779:
863:
349:
2272:. Hoboken, N.J.: John Wiley. pp. 490–492.
2001:
912:
119:
2239:
2151:
2114:Encyclopedia of Reagents for Organic Synthesis
2005:Ullmann's Encyclopedia of Industrial Chemistry
1701:DMF is effective at separating and suspending
2425:Chemical synthesis using supercritical fluids
1693:, which renders it safe to transport and use.
2578:. Oxford: Oxford University Press. pp.
2100:
1347:in the place of the two hydrogens. DMF is a
2689:
2643:"Dimethylformamide and alcohol intolerance"
2569:
1374:
2371:"Sur la préparation des amides en général"
428:
275:
233:
2666:
2540:
2481:
2455:
2422:Walter Leitner; Philip G. Jessop (1999).
2261:
1747:in the presence of a catalytic amount of
385:
40:Ball and stick model of dimethylformamide
2760:NIOSH Pocket Guide to Chemical Hazards.
2709:
2491:Bulletin de la Société Chimique de Paris
2465:Bulletin de la Société Chimique de Paris
2375:Bulletin de la Société Chimique de Paris
1888:NIOSH Pocket Guide to Chemical Hazards.
1815:
1771:published an article about DMF's use in
1639:(also known as the 'Vilsmeier reagent'):
1430:
2755:International Chemical Safety Card 0457
2605:
2563:
2390:
1940:Spectral Database for Organic Compounds
1589:, fibers, films, and surface coatings.
424:
327:
253:
2780:
2647:British Journal of Industrial Medicine
2368:
2190:
2188:
2147:
2145:
1997:
1995:
1993:
1991:
1930:
1928:
1905:
1903:
1883:
1881:
1879:
1769:Danish Environmental Protective Agency
1481:after hydrolysis in a reaction called
969:445 °C (833 °F; 718 K)
576:153 °C (307 °F; 426 K)
566:−61 °C (−78 °F; 212 K)
266:
2614:"3. Near-Infrared (NIR) Spectroscopy"
2518:Springer Science & Business Media
1542:or by reaction of dimethylamine with
1319:. Dimethylformamide is odorless, but
955:58 °C (136 °F; 331 K)
456:Key: ZMXDDKWLCZADIW-UHFFFAOYSA-N
213:
193:
2612:Haddon, R.; Itkis, M. (March 2008).
2397:Weissermel, K.; Arpe, H.-J. (2003).
2267:
2002:Bipp, H.; Kieczka, H. "Formamides".
1666:DMF is used as a solvent to recover
453:InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
50:Spacefill model of dimethylformamide
2185:
2142:
1988:
1925:
1900:
1876:
1601:, another useful method of forming
340:
310:
13:
2507:
2217:10.1016/B978-0-08-052349-1.00049-4
1642:
1573:. It is also used as a solvent in
1396:
1331:samples with an inert gas such as
908:
45:
35:
14:
2809:
2748:
1619:, in particular the synthesis of
2543:The Mizoroki–Heck Reaction
1726:DMF is a common solvent used in
1214:
821:
816:
811:
629:−0.3 (for the conjugate acid) (H
510:
504:
22:
2683:
2634:
2596:
2541:Oestreich, Martin, ed. (2009).
2534:
2501:
2475:
2449:
2415:
2362:
2330:
2321:
2286:
2233:
2205:Additions to CX π-Bonds, Part 2
2163:-alkylamino-benzaldehyde].
2094:
2085:
2040:
1593:It is used as a reagent in the
1560:
1210:(at 25 °C , 100 kPa).
2510:"Bouveault aldehyde synthesis"
2030:
1953:
1862:
1827:The Royal Society of Chemistry
1796:
1608:It is a common solvent in the
1390:DMF is a classic example of a
513:
498:
1:
2401:. Wiley-VCH. pp. 45–46.
2339:Journal of Chemical Education
2295:Journal of Chemical Education
2014:10.1002/14356007.a12_001.pub2
1790:
1657:solid phase peptide synthesis
1534:DMF is prepared by combining
1526:
1303:), this colourless liquid is
1095:(US health exposure limits):
783:−1.9416 ± 0.0012 MJ/mol
2428:. Wiley-VCH. pp. 408–.
1705:, and is recommended by the
1595:Bouveault aldehyde synthesis
1581:, and in the manufacture of
1551:supercritical carbon dioxide
1488:Dimethylformamide forms 1:1
1483:Bouveault aldehyde synthesis
1439:
7:
2731:10.7326/0003-4819-108-5-680
2719:Annals of Internal Medicine
2255:10.1002/0471264180.or056.02
1835:10.1039/9781849733069-FP001
1829:. 2014. pp. 841, 844.
1778:
1455:In one of its main uses in
1000:or concentration (LD, LC):
688:0.92 mPa·s (at 20 °C)
31:
10:
2814:
2493:. 3rd series (in French).
2467:. 3rd series (in French).
2377:. 3rd series (in French).
2166:Ber. Dtsch. Chem. Ges. A/B
1711:near infrared spectroscopy
1459:, DMF is a reagent in the
546:Odorless, fishy if impure
1759:
1204:
1138:
1089:
996:
792:
787:
756:−239.4 ± 1.2 kJ/mol
709:
692:
485:
465:
440:
103:
84:
65:
60:
30:
21:
2179:10.1002/cber.19270600118
2126:10.1002/047084289x.rd335
1812:, NIST web thermo tables
1735:metal–organic frameworks
1599:Vilsmeier-Haack reaction
1503:. It is classified as a
1467:, which attacks arenes.
1461:Vilsmeier–Haack reaction
1404:The ambient temperature
1375:Structure and properties
1063:3092 ppm (mouse, 2
876:Precautionary statements
2008:. Weinheim: Wiley-VCH.
1676:extractive distillation
1477:react with DMF to give
1471:Organolithium compounds
678:1.4305 (at 20 °C)
1659:and as a component of
1647:
1436:
1401:
1121:TWA 10 ppm (30 mg/m)
1108:TWA 10 ppm (30 mg/m)
919:
51:
41:
2547:John Wiley & Sons
2508:Li, Jie Jack (2014).
2268:Wang, Zerong (2009).
2201:Heathcock, Clayton H.
2118:John Wiley & Sons
1767:On 20 June 2018, the
1646:
1511:base parameters are E
1434:
1418:partition coefficient
1400:
986:Threshold limit value
918:
49:
39:
2570:Clayden, J. (2001).
2211:. pp. 777–794.
1810:-Dimethylmethanamide
1651:DMF penetrates most
1499:, and the hard acid
1085:5000 ppm (rat, 6 h)
1057:median concentration
901:(fire diamond)
96:-Dimethylmethanamide
67:Preferred IUPAC name
2659:10.1136/oem.36.1.63
2369:Verley, A. (1893).
2307:1996JChEd..73..701V
2063:1985Natur.313..384T
1974:1956JChPh..25.1228G
1936:"Dimethylformamide"
1911:"Dimethylformamide"
1281:. Its structure is
1145:Related alkanamides
583:Solubility in water
528: g·mol
175:Beilstein Reference
18:
2623:. NIST. p. 20
2520:. pp. 72–73.
2110:-Dimethylformamide
1648:
1557:-based catalysts.
1437:
1402:
1392:fluxional molecule
1317:chemical reactions
1237:Infobox references
1139:Related compounds
1130:(Immediate danger)
920:
536:Colourless liquid
78:-Dimethylformamide
52:
42:
17:Dimethylformamide
16:
2690:Magnus Løfstedt.
2574:Organic Chemistry
2527:978-3-319-03979-4
2435:978-3-527-29605-7
2385:potassium formate
2351:10.1021/ed054p612
2315:10.1021/ed073p701
2057:(6001): 384–386.
1982:10.1063/1.1743184
1844:978-0-85404-182-4
1475:Grignard reagents
1465:Vilsmeier reagent
1457:organic synthesis
1385:infrared spectrum
1301:dimethyl fumarate
1249:Dimethylformamide
1245:Chemical compound
1243:
1242:
1176:Related compounds
1042:
1036:
1030:
1024:
846:Hazard statements
729:146.05 J/(K·mol)
409:CompTox Dashboard
329:Dimethylformamide
145:Interactive image
87:Dimethylformamide
56:
55:
2805:
2769:
2743:
2742:
2713:
2707:
2706:
2704:
2703:
2694:. Archived from
2687:
2681:
2680:
2670:
2638:
2632:
2631:
2629:
2628:
2618:
2609:
2603:
2600:
2594:
2593:
2577:
2567:
2561:
2560:
2538:
2532:
2531:
2516:(5th ed.).
2505:
2499:
2498:
2483:Bouveault, Louis
2479:
2473:
2472:
2457:Bouveault, Louis
2453:
2447:
2446:
2444:
2442:
2419:
2413:
2412:
2394:
2388:
2382:
2366:
2360:
2354:
2334:
2328:
2325:
2319:
2318:
2290:
2284:
2283:
2265:
2259:
2258:
2237:
2231:
2230:
2192:
2183:
2182:
2153:Vilsmeier, Anton
2149:
2140:
2139:
2098:
2092:
2089:
2083:
2082:
2071:10.1038/313384a0
2044:
2038:
2034:
2028:
2027:
1999:
1986:
1985:
1968:(6): 1228–1234.
1957:
1951:
1950:
1948:
1947:
1932:
1923:
1922:
1907:
1898:
1897:
1885:
1874:
1873:
1866:
1860:
1859:
1819:
1813:
1800:
1703:carbon nanotubes
1637:imidoyl chloride
1633:thionyl chloride
1625:carboxylic acids
1575:peptide coupling
1446:sodium hydroxide
1294:
1280:
1257:chemical formula
1253:organic compound
1227:
1221:
1218:
1217:
1161:Diethylformamide
1156:-Methylformamide
1079:lowest published
1040:
1034:
1028:
1023:(rabbit, dermal)
1022:
975:Explosive limits
940:
933:
926:
911:
891:
887:
883:
869:
865:
861:
857:
853:
825:
820:
815:
779:
752:
725:
710:Thermochemistry
665:Refractive index
527:
515:
512:
506:
500:
493:Chemical formula
433:
432:
417:
415:
389:
353:
342:
331:
314:
287:
279:
268:
257:
237:
217:
197:
165:
147:
123:
32:
26:
19:
15:
2813:
2812:
2808:
2807:
2806:
2804:
2803:
2802:
2778:
2777:
2751:
2746:
2714:
2710:
2701:
2699:
2688:
2684:
2639:
2635:
2626:
2624:
2616:
2610:
2606:
2601:
2597:
2590:
2568:
2564:
2557:
2539:
2535:
2528:
2506:
2502:
2480:
2476:
2454:
2450:
2440:
2438:
2436:
2420:
2416:
2409:
2395:
2391:
2367:
2363:
2335:
2331:
2326:
2322:
2291:
2287:
2280:
2266:
2262:
2238:
2234:
2227:
2197:Trost, Barry M.
2193:
2186:
2150:
2143:
2136:
2099:
2095:
2090:
2086:
2045:
2041:
2035:
2031:
2024:
2000:
1989:
1958:
1954:
1945:
1943:
1934:
1933:
1926:
1909:
1908:
1901:
1886:
1877:
1868:
1867:
1863:
1856:
1852:
1845:
1821:
1820:
1816:
1801:
1797:
1793:
1781:
1762:
1746:
1728:electrospinning
1721:carbon monoxide
1661:paint strippers
1563:
1544:carbon monoxide
1529:
1518:
1514:
1505:hard Lewis base
1497:
1450:decarbonylation
1442:
1426:
1377:
1368:
1357:aprotic solvent
1321:technical-grade
1293:
1288:
1282:
1279:
1275:
1259:
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1239:
1234:
1233:
1232: ?)
1223:
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777:
771:
767:
764:
763:Std enthalpy of
753:
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736:Std enthalpy of
726:
719:
702:
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644:
632:
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113:
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12:
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5:
2811:
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2800:
2795:
2793:Amide solvents
2790:
2776:
2775:
2770:
2757:
2750:
2749:External links
2747:
2745:
2744:
2725:(5): 680–686.
2708:
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2361:
2329:
2320:
2301:(8): 701–707.
2285:
2278:
2260:
2249:(2): 355–686.
2232:
2225:
2184:
2173:(1): 119–122.
2141:
2134:
2093:
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2039:
2029:
2023:978-3527306732
2022:
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1679:
1664:
1641:
1640:
1621:acyl chlorides
1613:
1606:
1567:acrylic fibers
1562:
1559:
1536:methyl formate
1528:
1525:
1516:
1512:
1495:
1441:
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1424:
1406:H NMR spectrum
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1208:standard state
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1201:
1199:
1198:
1193:
1180:
1178:
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1172:
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1168:
1166:Deuterated DMF
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1016:
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1001:
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992:30 mg/m (TWA)
990:
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947:
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886:P305+P351+P338
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2698:on 2021-09-03
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2589:0-19-850346-6
2585:
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2558:
2556:9780470716069
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2408:3-527-30578-5
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2226:9780080405933
2222:
2218:
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2206:
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2198:
2191:
2189:
2180:
2176:
2172:
2169:(in German).
2168:
2167:
2162:
2158:
2154:
2148:
2146:
2137:
2135:9780470842898
2131:
2127:
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2015:
2011:
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1962:J. Chem. Phys
1956:
1942:. Japan: AIST
1941:
1937:
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1929:
1920:
1916:
1912:
1906:
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1825:. Cambridge:
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1677:
1673:
1672:1,3-butadiene
1669:
1665:
1662:
1658:
1654:
1650:
1649:
1645:
1638:
1634:
1630:
1626:
1622:
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1614:
1611:
1610:Heck reaction
1607:
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1600:
1596:
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1545:
1541:
1540:dimethylamine
1537:
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1372:
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1362:
1361:boiling point
1358:
1354:
1350:
1346:
1345:methyl groups
1343:, having two
1342:
1338:
1334:
1330:
1326:
1325:dimethylamine
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1297:dimethylfuran
1289:
1271:
1268:
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1137:
1133:
1129:
1125:
1124:
1120:
1117:(Recommended)
1116:
1112:
1111:
1107:
1104:(Permissible)
1103:
1099:
1098:
1094:
1093:
1088:
1084:
1080:
1071:
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1062:
1058:
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1038:
1035:(mouse, oral)
1032:
1026:
1020:
1019:
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987:
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782:
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766:
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747:
739:
733:
732:
728:
723:
718:
717:Heat capacity
714:
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708:
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701:
700:Dipole moment
697:
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579:
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572:Boiling point
570:
569:
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563:
562:Melting point
560:
559:
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522:
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489:
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471:
464:
450:
449:
446:
439:
431:
427:
426:DTXSID6020515
423:
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293:
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278:
274:
271:
269:
267:ECHA InfoCard
264:
263:
256:
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83:
77:
73:
68:
64:
59:
48:
44:
38:
34:
33:
29:
25:
20:
2798:Hepatotoxins
2722:
2718:
2711:
2700:. Retrieved
2696:the original
2685:
2653:(1): 63–66.
2650:
2646:
2636:
2625:. Retrieved
2620:
2607:
2598:
2573:
2565:
2542:
2536:
2513:
2503:
2497:: 1322–1327.
2494:
2490:
2477:
2471:: 1306–1322.
2468:
2464:
2451:
2439:. Retrieved
2424:
2417:
2398:
2392:
2378:
2374:
2364:
2342:
2338:
2332:
2323:
2298:
2294:
2288:
2269:
2263:
2246:
2241:
2235:
2204:
2170:
2164:
2160:
2156:
2113:
2109:
2105:
2102:
2096:
2087:
2054:
2048:
2042:
2032:
2003:
1965:
1961:
1955:
1944:. Retrieved
1939:
1914:
1864:
1848:
1822:
1817:
1807:
1803:
1798:
1782:
1766:
1763:
1750:
1741:
1696:
1617:acyl halides
1585:, synthetic
1564:
1561:Applications
1548:
1533:
1530:
1515:= 2.19 and C
1487:
1469:
1454:
1443:
1421:
1411:
1403:
1389:
1379:As for most
1378:
1359:with a high
1248:
1247:
1188:
1184:
1153:
1091:
997:
962:Autoignition
897:
837:
794:
772:
745:
721:
668:
620:
595:
362:RTECS number
215:ChEMBL268291
104:Identifiers
93:
89:
85:Other names
75:
71:
2345:: 612–613.
2243:Org. React.
1709:for use in
1597:and in the
1414:Henry's law
1371:reactions.
1353:hydrophilic
1191:-methylurea
1041:(rat, oral)
1029:(rat, oral)
1012:median dose
998:Lethal dose
964:temperature
951:Flash point
832:Signal word
556:0.948 g/mL
533:Appearance
486:Properties
273:100.000.617
195:CHEBI:17741
2788:Formamides
2782:Categories
2702:2019-06-13
2627:2012-06-28
2381:: 690–692.
1946:2012-06-28
1791:References
1783:The acute
1749:potassium
1579:pesticides
1527:Production
1337:sonicating
979:2.2–15.2%
806:Pictograms
765:combustion
693:Structure
654:Absorbance
521:Molar mass
387:8696NH0Y2X
226:ChemSpider
132:3D model (
111:CAS Number
2357:ECW model
1773:squishies
1753:-butoxide
1691:agamassan
1686:acetylene
1603:aldehydes
1583:adhesives
1555:ruthenium
1521:C-B plots
1509:ECW model
1479:aldehydes
1440:Reactions
1420:log
1341:formamide
1283:HC(=O)−N(
1255:with the
1187:-Nitroso-
1039:3.5 g/kg
1033:3.7 g/kg
1027:2.8 g/kg
1021:1.5 g/kg
890:P308+P313
797:labelling
738:formation
684:Viscosity
588:Miscible
398:UN number
369:LQ2100000
294:200-679-5
286:EC Number
2768:(NIOSH).
2485:(1904).
2459:(1904).
2209:Elsevier
2203:(eds.).
2079:36740734
1921:(NIOSH).
1896:(NIOSH).
1779:Toxicity
1723:ligands.
1713:of such.
1670:such as
1653:plastics
1587:leathers
1571:plastics
1507:and its
1329:sparging
1305:miscible
1134:500 ppm
898:NFPA 704
788:Hazards
477:CN(C)C=O
246:DrugBank
2762:"#0226"
2739:3358569
2668:1008494
2580:276–296
2441:27 June
2303:Bibcode
2059:Bibcode
1970:Bibcode
1890:"#0226"
1668:olefins
1490:adducts
1313:solvent
1230:what is
1228: (
705:3.86 D
648:270 nm
617:Acidity
611:516 Pa
601:−0.829
552:Density
338:PubChem
255:DB01844
180:605365
121:68-12-2
2737:
2677:444443
2675:
2665:
2586:
2553:
2524:
2432:
2405:
2276:
2223:
2132:
2077:
2050:Nature
2037:1–124.
2020:
1857:group.
1841:
1760:Safety
1629:oxalyl
1627:using
1553:using
1501:phenol
1381:amides
1335:or by
1251:is an
1225:verify
1222:
838:Danger
639:UV-vis
526:73.095
470:SMILES
312:C03134
206:ChEMBL
163:B00545
155:3DMet
61:Names
2617:(pdf)
2075:S2CID
1684:Pure
1623:from
1349:polar
1333:argon
1309:water
1307:with
1299:, or
1092:NIOSH
988:(TLV)
658:1.00
445:InChI
402:2265
186:ChEBI
134:JSmol
2735:PMID
2673:PMID
2584:ISBN
2551:ISBN
2522:ISBN
2443:2011
2430:ISBN
2403:ISBN
2274:ISBN
2221:ISBN
2130:ISBN
2018:ISBN
1839:ISBN
1785:LD50
1751:tert
1740:DMF-
1707:NIST
1674:via
1569:and
1538:and
1473:and
1315:for
1128:IDLH
882:P280
868:H360
864:H332
860:H319
856:H312
852:H226
594:log
542:Odor
378:UNII
351:6228
323:MeSH
303:KEGG
235:5993
2727:doi
2723:108
2663:PMC
2655:doi
2347:doi
2311:doi
2251:doi
2213:doi
2175:doi
2122:doi
2067:doi
2055:313
2010:doi
1978:doi
1831:doi
1631:or
1285:−CH
1272:(CH
1196:ENU
1115:REL
1102:PEL
795:GHS
776:298
749:298
643:max
633:O)
414:EPA
341:CID
98:DMF
2784::
2764:.
2733:.
2721:.
2671:.
2661:.
2651:36
2649:.
2645:.
2582:.
2549:.
2545:.
2512:.
2495:31
2469:31
2359:.
2343:54
2341:.
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