398:
245:
31:
44:
54:
781:
771:
876:
776:
872:
1206:
877:
875:
1684:
2003:"Cone angles for amine ligands. X-ray crystal structures and equilibrium measurements for ammonia, ethylamine, diethylamine, and triethylamine complexes with the [bis(dimethylphosphino)ethane]methylpalladium(II) cation"
789:
751:
893:
847:
1777:
1755:
1551:. It is also used in mosquito and vector control labs to anesthetize mosquitoes. This is done to preserve any viral material that might be present during species identification.
1020:
1219:
1909:
878:
1366:
Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C. It is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether.
1905:
437:
1925:"Applications of light-induced electron-transfer reactions. Coupling of hydrogen generation with photoreduction of ruthenium(II) complexes by triethylamine"
1964:"Photoinduced electron transfer reactions of transition-metal complexes with amines. Mechanistic studies of alternate pathways to back electron transfer"
900:
1599:
flowers have a heavy, complicated scent, the distinctive part of which is triethylamine, which is also one of the first chemicals produced by a
720:
1713:
839:
2087:
2057:
1881:
1653:
693:
30:
43:
1856:
1419:
which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. (R, R' =
412:
1170:
1537:
1506:
53:
1791:
1483:
843:
1226:
1562:
833:
345:
376:
2129:
886:
780:
1637:
1463:
1044:
1031:
613:
1451:
Like other tertiary amines, it catalyzes the formation of urethane foams and epoxy resins. It is also useful in
1120:
252:
2170:
1669:
1110:
923:
290:
1815:
770:
1548:
1526:
1137:
636:
296:
775:
240:
1277:
1152:
1147:
1092:
202:
1495:
1285:
947:
803:
763:
568:
1505:
Triethylamine salts, like any other tertiary ammonium salts, are used as an ion-interaction reagent in
2165:
2077:
1600:
1352:
of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions at that pH. The
851:
73:
1268:
N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with
393:
1710:
1634:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1452:
108:
1899:
1273:
1115:
162:
142:
1962:
DeLaive, Patricia J.; Foreman, Thomas K.; Giannotti, Charles; Whitten, David G. (August 1980).
2083:
2053:
2022:
1983:
1944:
1887:
1877:
1852:
1649:
1514:
1513:. Unlike quaternary ammonium salts, tertiary ammonium salts are much more volatile, therefore
1416:
1289:
1242:
1132:
2073:
2045:
2014:
1975:
1936:
1844:
1641:
1558:
1400:
1356:
1293:
1246:
1105:
649:
547:
460:
1532:
Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g.
354:
1729:
1717:
1604:
1456:
1370:
1269:
1142:
936:
222:
17:
2128:
The book of general ignorance. John Lloyd & John
Mitchinson. Faber & Faber 2006,
1359:, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and
118:
397:
244:
182:
1668:
X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348
1197:
1087:
821:
592:
581:
2159:
1561:
of triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in
1412:
1353:
1082:
674:
536:
526:
233:
2104:
2002:
1963:
1924:
1581:
1577:
1391:. Owing to its steric bulk, it forms complexes with transition metals reluctantly.
1180:
1100:
2145:
809:
1923:
DeLaive, Patricia J.; Sullivan, B. P.; Meyer, T. J.; Whitten, D. G. (July 1979).
318:
1645:
1555:
1360:
1262:
1008:
975:
912:
2150:
1751:
1573:
1569:
1510:
1377:
1305:
558:
485:
213:
2049:
2026:
1987:
1948:
1891:
1848:
1769:
1596:
1533:
1499:
1175:
817:
365:
1572:
in combination with nitric acid, and was used as a component in the German
1529:(resins dispersed in water rather than solvents) as a neutralizing agent.
1839:
Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000).
1608:
1585:
1568:
Triethylamine was discovered by the
Germans during the early 1940s to be
1491:
1185:
899:
892:
885:
858:
2018:
1979:
1940:
1588:
and 50% triethylamine as a starting fluid to ignite its rocket engine.
1403:. For example, it is commonly used as a base during the preparation of
1369:
Laboratory samples of triethylamine can be purified by distilling from
1309:
1281:
516:
305:
253:
1816:"tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY"
1544:
1388:
1381:
193:
1565:, often in a gradient to purify nucleotides and other biomolecules.
1196:
Except where otherwise noted, data are given for materials in their
813:
541:
88.6 to 89.8 °C; 191.4 to 193.5 °F; 361.7 to 362.9 K
279:
1612:
1420:
1408:
1404:
1276:, for which TEA is also a common abbreviation. It is a colourless
825:
329:
173:
141:
131:
1424:
1057:
506:
270:
1498:
and is useful as an intermediate for manufacturing medicines,
1487:
1774:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1462:
Triethylamine is readily alkylated to give the corresponding
1399:
Triethylamine is commonly employed in organic synthesis as a
1706:
1704:
1525:
Triethylamine is commonly used in the production of anionic
381:
52:
42:
2079:
Ignition!: An
Informal History of Liquid Rocket Propellants
1380:
that forms adducts with a variety of Lewis acids, such as
1486:
for textile auxiliaries and quaternary ammonium salts of
870:
1876:. Chai, Christina Li Lin (Seventh ed.). Amsterdam.
1214:
2001:
Seligson, Allen L.; Trogler, William C. (March 1991).
1288:(Hünig's base), triethylamine is commonly employed in
1778:
National
Institute for Occupational Safety and Health
1756:
National
Institute for Occupational Safety and Health
1363:
powder, which decomposes when heated to 261 °C.
1792:"Ethanolamine Compounds (MEA, DEA, TEA And Others)"
1482:Triethylamine is mainly used in the production of
1603:. Due to the scent, it is considered unlucky in
531:−114.70 °C; −174.46 °F; 158.45 K
317:
1280:liquid with a strong fishy odor reminiscent of
874:
117:
2042:Encyclopedia of Reagents for Organic Synthesis
394:DTXSID301024181 DTXSID3024366, DTXSID301024181
8:
2151:CDC - NIOSH Pocket Guide to Chemical Hazards
1679:
1677:
1908:) CS1 maint: multiple names: authors list (
1415:. Such reactions lead to the production of
421:InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3
1904:: CS1 maint: location missing publisher (
1615:are also said to possess a similar odour.
1543:Triethylamine is the active ingredient in
396:
243:
221:
22:
2082:. Rutgers University Press. p. 302.
353:
2007:Journal of the American Chemical Society
1968:Journal of the American Chemical Society
1929:Journal of the American Chemical Society
1750:NIOSH Pocket Guide to Chemical Hazards.
1624:
1601:dead human body when it begins to decay
1517:can be used while performing analysis.
442:
417:
392:
295:
2040:Sorgi, K. L. (2001). "Triethylamine".
1897:
1745:
1743:
1741:
1376:In alkane solvents triethylamine is a
931:312 °C (594 °F; 585 K)
234:
424:Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N
201:
181:
47:Ball and stick model of triethylamine
7:
2103:Brügge, Norbert (24 February 2020).
1874:Purification of Laboratory Chemicals
917:−15 °C (5 °F; 258 K)
96:Triethylamine (no longer IUPAC name)
2044:. New York: John Wiley & Sons.
308:
278:
2105:"The Soviet "Scud" missile family"
1872:F., Armarego, W. L. (2012-10-17).
14:
1304:Triethylamine is prepared by the
626:10.75 (for the conjugate acid) (H
1607:to bring hawthorn into a house.
1204:
779:
774:
769:
478:
472:
57:Spacefill model of triethylamine
29:
1200:(at 25 °C , 100 kPa).
1171:Unsymmetrical dimethylhydrazine
563:miscible with organic solvents
1638:The Royal Society of Chemistry
1547:, a product for anesthetizing
1538:2,4-dichlorophenoxyacetic acid
1507:ion interaction chromatography
466:
1:
1484:quaternary ammonium compounds
1025:(US health exposure limits):
1563:reverse phase chromatography
741:−4.37763 to −4.37655 MJ mol
2146:US EPA - Air Toxics Website
1820:www.guidetopharmacology.org
1646:10.1039/9781849733069-FP001
964:or concentration (LD, LC):
954:2 ppm (8 mg/m) (TWA),
38:
2187:
1711:David Evans Research Group
15:
1494:and acid neutralizer for
1194:
1068:
1019:
960:
750:
745:
667:
453:
433:
408:
101:
91:
72:
67:
37:
28:
2050:10.1002/047084289X.rt217
1849:10.1002/14356007.a02_001
1527:Polyurethane dispersions
1464:quaternary ammonium salt
1300:Synthesis and properties
1111:Dimethylaminopropylamine
834:Precautionary statements
16:Not to be confused with
1261:, commonly abbreviated
1138:Tris(2-aminoethyl)amine
1015:1425 ppm (mouse, 2 hr)
956:4 ppm (17 mg/m) (STEL)
637:Magnetic susceptibility
1734:(11th ed.). 9582.
1511:amphiphilic properties
1496:condensation reactions
1435:NH + R'C(O)Cl + Et
1153:HN3 (nitrogen mustard)
1148:HN1 (nitrogen mustard)
1128:-Diisopropylethylamine
1038:TWA 25 ppm (100 mg/m)
881:
58:
48:
1640:. 2014. p. 671.
1502:and other chemicals.
1286:diisopropylethylamine
1096:-Nitrosodimethylamine
948:Threshold limit value
880:
56:
46:
1689:www.sigmaaldrich.com
863:(fire diamond)
74:Preferred IUPAC name
2019:10.1021/ja00007a028
1980:10.1021/ja00537a037
1941:10.1021/ja00508a070
1584:, a mixture of 50%
1576:rocket. The Soviet
1453:dehydrohalogenation
553:112.4 g/L at 20 °C
548:Solubility in water
493: g·mol
163:Beilstein Reference
25:
1716:2012-01-21 at the
1592:Natural occurrence
1274:tetraethylammonium
1227:Infobox references
1116:Diethylenetriamine
1069:Related compounds
1060:(Immediate danger)
882:
511:Fishy, ammoniacal
501:Colourless liquid
85:-Diethylethanamine
59:
49:
23:
2089:978-0-8135-9918-2
2074:Clark, John Drury
2059:978-0-471-93623-7
1974:(17): 5627–5631.
1935:(14): 4007–4008.
1883:978-0-12-382162-1
1841:Amines, Aliphatic
1655:978-0-85404-182-4
1515:mass spectrometry
1417:hydrogen chloride
1290:organic synthesis
1243:chemical compound
1235:Chemical compound
1233:
1232:
1163:Related compounds
1133:Triisopropylamine
1051:None established
994:
988:
804:Hazard statements
377:CompTox Dashboard
143:Interactive image
63:
62:
2178:
2133:
2126:
2120:
2119:
2117:
2115:
2100:
2094:
2093:
2070:
2064:
2063:
2037:
2031:
2030:
2013:(7): 2520–2527.
1998:
1992:
1991:
1959:
1953:
1952:
1920:
1914:
1913:
1903:
1895:
1869:
1863:
1862:
1836:
1830:
1829:
1827:
1826:
1812:
1806:
1805:
1803:
1802:
1788:
1782:
1781:
1766:
1760:
1759:
1747:
1736:
1735:
1726:
1720:
1708:
1699:
1698:
1696:
1695:
1681:
1672:
1666:
1660:
1659:
1632:"Front Matter".
1629:
1457:Swern oxidations
1308:of ammonia with
1217:
1211:
1208:
1207:
1106:Diisopropylamine
1009:lowest published
992:
987:(dermal, rabbit)
986:
937:Explosive limits
902:
895:
888:
873:
853:
849:
845:
841:
827:
823:
819:
815:
811:
783:
778:
773:
737:
710:
683:
668:Thermochemistry
650:Refractive index
643:-81.4·10 cm/mol
630:O), 9.00 (DMSO)
586:6.899–8.506 kPa
492:
480:
474:
468:
461:Chemical formula
401:
400:
385:
383:
357:
321:
310:
299:
282:
255:
247:
236:
225:
205:
185:
145:
121:
39:
33:
26:
2186:
2185:
2181:
2180:
2179:
2177:
2176:
2175:
2171:Tertiary amines
2156:
2155:
2142:
2137:
2136:
2127:
2123:
2113:
2111:
2102:
2101:
2097:
2090:
2076:(23 May 2018).
2072:
2071:
2067:
2060:
2039:
2038:
2034:
2000:
1999:
1995:
1961:
1960:
1956:
1922:
1921:
1917:
1896:
1884:
1871:
1870:
1866:
1859:
1838:
1837:
1833:
1824:
1822:
1814:
1813:
1809:
1800:
1798:
1790:
1789:
1785:
1770:"Triethylamine"
1768:
1767:
1763:
1749:
1748:
1739:
1731:The Merck Index
1728:
1727:
1723:
1718:Wayback Machine
1709:
1702:
1693:
1691:
1685:"MSDS - 471283"
1683:
1682:
1675:
1667:
1663:
1656:
1631:
1630:
1626:
1621:
1605:British culture
1594:
1523:
1509:, due to their
1490:. It is also a
1477:
1473:
1446:
1442:
1438:
1434:
1397:
1385:
1371:calcium hydride
1351:
1343:
1339:
1335:
1331:
1327:
1323:
1319:
1302:
1292:, usually as a
1270:triethanolamine
1267:
1260:
1256:
1252:
1236:
1229:
1224:
1223:
1222: ?)
1213:
1209:
1205:
1201:
1190:
1164:
1157:
1143:Mechlorethamine
1076:
1061:
1048:
1035:
1012:
1006:
997:
979:
973:
955:
951:
928:
925:
907:
906:
905:
904:
897:
890:
883:
879:
871:
836:
806:
792:
766:
738:
735:
729:
725:
722:
721:Std enthalpy of
711:
708:
702:
698:
695:
694:Std enthalpy of
687:216.43 J K mol
684:
677:
660:
658:
640:
629:
622:
605:
603:
594:
550:
490:
477:
471:
463:
449:
446:
441:
440:
429:
426:
425:
422:
416:
415:
404:
386:
379:
360:
340:
324:
311:
285:
265:
228:
208:
188:
165:
148:
135:
124:
111:
97:
95:
94:(Triethyl)amine
87:
86:
21:
18:Triethanolamine
12:
11:
5:
2184:
2182:
2174:
2173:
2168:
2158:
2157:
2154:
2153:
2148:
2141:
2140:External links
2138:
2135:
2134:
2121:
2095:
2088:
2065:
2058:
2032:
1993:
1954:
1915:
1882:
1864:
1857:
1831:
1807:
1796:Safe Cosmetics
1783:
1761:
1737:
1721:
1700:
1673:
1661:
1654:
1623:
1622:
1620:
1617:
1593:
1590:
1522:
1519:
1480:
1479:
1475:
1471:
1455:reactions and
1449:
1448:
1444:
1440:
1439:N → R'C(O)NR
1436:
1432:
1413:acyl chlorides
1396:
1393:
1383:
1349:
1346:
1345:
1341:
1337:
1333:
1329:
1325:
1321:
1317:
1301:
1298:
1265:
1258:
1254:
1250:
1234:
1231:
1230:
1225:
1203:
1202:
1198:standard state
1195:
1192:
1191:
1189:
1188:
1183:
1178:
1173:
1167:
1165:
1162:
1159:
1158:
1156:
1155:
1150:
1145:
1140:
1135:
1130:
1118:
1113:
1108:
1103:
1098:
1090:
1088:Trimethylamine
1085:
1079:
1077:
1075:Related amines
1074:
1071:
1070:
1066:
1065:
1062:
1056:
1053:
1052:
1049:
1043:
1040:
1039:
1036:
1030:
1027:
1026:
1017:
1016:
1013:
1004:
1002:
999:
998:
996:
995:
989:
982:
980:
971:
969:
966:
965:
958:
957:
952:
946:
943:
942:
939:
933:
932:
929:
922:
919:
918:
915:
909:
908:
898:
891:
884:
869:
868:
867:
866:
864:
855:
854:
848:P305+P351+P338
837:
832:
829:
828:
807:
802:
799:
798:
793:
788:
785:
784:
767:
762:
759:
758:
748:
747:
743:
742:
739:
733:
727:
719:
716:
715:
712:
706:
700:
692:
689:
688:
685:
673:
670:
669:
665:
664:
661:
656:
648:
645:
644:
641:
635:
632:
631:
627:
624:
620:
610:
609:
608:66 μmol Pa kg
606:
601:
591:
588:
587:
584:
582:Vapor pressure
578:
577:
574:
565:
564:
561:
555:
554:
551:
546:
543:
542:
539:
533:
532:
529:
523:
522:
519:
513:
512:
509:
503:
502:
499:
495:
494:
488:
482:
481:
475:
469:
464:
459:
456:
455:
451:
450:
448:
447:
444:
436:
435:
434:
431:
430:
428:
427:
423:
420:
419:
411:
410:
409:
406:
405:
403:
402:
389:
387:
375:
372:
371:
368:
362:
361:
359:
358:
350:
348:
342:
341:
339:
338:
334:
332:
326:
325:
323:
322:
314:
312:
304:
301:
300:
293:
287:
286:
284:
283:
275:
273:
267:
266:
264:
263:
259:
257:
249:
248:
238:
230:
229:
227:
226:
218:
216:
210:
209:
207:
206:
198:
196:
190:
189:
187:
186:
178:
176:
170:
169:
166:
161:
158:
157:
154:
153:Abbreviations
150:
149:
147:
146:
138:
136:
129:
126:
125:
123:
122:
114:
112:
107:
104:
103:
99:
98:
93:
89:
88:
77:
76:
70:
69:
65:
64:
61:
60:
50:
35:
34:
24:Triethylamine
13:
10:
9:
6:
4:
3:
2:
2183:
2172:
2169:
2167:
2164:
2163:
2161:
2152:
2149:
2147:
2144:
2143:
2139:
2131:
2125:
2122:
2110:
2106:
2099:
2096:
2091:
2085:
2081:
2080:
2075:
2069:
2066:
2061:
2055:
2051:
2047:
2043:
2036:
2033:
2028:
2024:
2020:
2016:
2012:
2008:
2004:
1997:
1994:
1989:
1985:
1981:
1977:
1973:
1969:
1965:
1958:
1955:
1950:
1946:
1942:
1938:
1934:
1930:
1926:
1919:
1916:
1911:
1907:
1901:
1893:
1889:
1885:
1879:
1875:
1868:
1865:
1860:
1858:3-527-30673-0
1854:
1850:
1846:
1842:
1835:
1832:
1821:
1817:
1811:
1808:
1797:
1793:
1787:
1784:
1779:
1775:
1771:
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1125:
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1101:Diethylamine
1093:
1021:
961:
924:Autoignition
859:
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752:
730:
714:−169 kJ mol
703:
679:
653:
617:
598:
570:
521:0.7255 g mL
330:RTECS number
203:ChEMBL284057
102:Identifiers
92:Other names
82:
78:
2166:Alkylamines
1556:bicarbonate
1549:fruit flies
1361:hygroscopic
993:(oral, rat)
976:median dose
962:Lethal dose
926:temperature
913:Flash point
790:Signal word
593:Henry's law
498:Appearance
454:Properties
241:100.004.064
183:CHEBI:35026
2160:Categories
1825:2020-06-17
1801:2020-06-17
1694:2020-06-17
1619:References
1574:Wasserfall
1570:hypergolic
1521:Niche uses
1500:pesticides
1378:Lewis base
1306:alkylation
991:730 mg kg
985:580 mg kg
764:Pictograms
723:combustion
559:Solubility
486:Molar mass
355:VOU728O6AY
214:ChemSpider
130:3D model (
109:CAS Number
2109:b14643.de
2027:0002-7863
1988:0002-7863
1949:0002-7863
1900:cite book
1892:820853648
1582:TONKA-250
1534:Triclopyr
1245:with the
1176:Biguanide
755:labelling
696:formation
445:CCN(CC)CC
366:UN number
337:YE0175000
262:204-469-4
254:EC Number
1780:(NIOSH).
1758:(NIOSH).
1714:Archived
1609:Gangrene
1597:Hawthorn
1586:xylidine
1492:catalyst
1328:OH → N(C
1278:volatile
1186:Agmatine
1064:200 ppm
860:NFPA 704
746:Hazards
639:(χ)
595:constant
119:121-44-8
2114:29 July
1752:"#0633"
1470:RI + Et
1389:phenols
1310:ethanol
1284:. Like
1282:ammonia
1247:formula
1241:is the
1220:what is
1218: (
941:1.2–8%
614:Acidity
597: (
517:Density
491:101.193
306:PubChem
168:605283
2086:
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1986:
1947:
1890:
1880:
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1652:
1545:FlyNap
1474:N → Et
1409:amides
1405:esters
1348:The pK
1215:verify
1212:
796:Danger
663:1.401
576:1.647
438:SMILES
280:C14691
194:ChEMBL
68:Names
2132:, BBC
1613:semen
1580:used
1443:+ Et
1421:alkyl
1411:from
1340:+ 3 H
1320:+ 3 C
1022:NIOSH
950:(TLV)
413:InChI
370:1296
174:ChEBI
132:JSmol
2116:2022
2084:ISBN
2054:ISBN
2023:ISSN
1984:ISSN
1945:ISSN
1910:link
1906:link
1888:OCLC
1878:ISBN
1853:ISBN
1650:ISBN
1611:and
1559:salt
1554:The
1536:and
1488:dyes
1447:NHCl
1425:aryl
1407:and
1401:base
1387:and
1357:salt
1294:base
1249:N(CH
1058:IDLH
852:P310
844:P280
840:P210
826:H332
822:H314
818:H312
814:H302
810:H225
569:log
507:Odor
346:UNII
319:8471
291:MeSH
271:KEGG
223:8158
156:TEA
2046:doi
2015:doi
2011:113
1976:doi
1972:102
1937:doi
1933:101
1845:doi
1670:PDF
1642:doi
1478:NRI
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