412:
287:
995:
990:
1000:
41:
603:
1114:
50:
1189:
598:
78:
593:
588:
1061:
69:
1126:
914:
791:
1743:
Faria, Jéssica Venância; Vegi, Percilene
Fazolin; Miguita, Ana Gabriella Carvalho; dos Santos, Maurício Silva; Boechat, Nubia; Bernardino, Alice Maria Rolim (1 November 2017). "Recently reported biological activities of pyrazole compounds".
1394:
Nozari, M., Addison, A., Reeves, G.T, Zeller, M., Jasinski, J.P., Kaur, M., Gilbert, J. G., Hamilton, C. R., Popovitch, J. M., Wolf, L. M., Crist, L. E., Bastida, N., (2018) Journal of heterocyclic
Chemistry 55, 6, 1291-1307.
611:
568:
1322:
1195:
721:
725:
1507:
Outirite, Moha; Lebrini, Mounim; Lagrenée, Michel; Bentiss, Fouad (2008). "New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating".
1315:
1928:
804:
1480:
461:
717:
1727:
1274:
1364:
Schmidt, Andreas; Dreger, Andrij (2011). "Recent
Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses".
1884:
A. Schmidt; A. Dreger (2011). "Recent
Advances in the Chemistry of Pyrazoles. Part 2. Reactions and N-Heterocyclic Carbenes of Pyrazole".
1840:
Jeschke, Peter (2021). "Current Trends in the Design of
Fluorine-Containing Agrochemicals". In Szabó, Kálmán; Selander, Nicklas (eds.).
1710:
Kabi, Arup K.; Sravani, Sattu; Gujjarappa, Raghuram; et al. (2022). "Overview on
Biological Activities of Pyrazole Derivatives".
1857:
1824:
1509:
1348:
426:
1807:
Walter, Harald (2016). "Fungicidal
Succinate-Dehydrogenase-Inhibiting Carboxamides". In Lamberth, Clemens; Dinges, Jürgen (eds.).
1923:
757:
705:
667:
369:
602:
390:
765:
597:
1258:
855:
811:
545:
1167:. The pyrazole ring is found within a variety of pesticides as fungicides, insecticides and herbicides, including
294:
655:
761:
1918:
1290:
1199:
925:
689:
587:
282:
1546:
994:
1183:. Pyrazole moieties are listed among the highly used ring systems for small molecule drugs by the US FDA
1137:
1617:
1044:
1036:
625:
592:
580:
224:
112:
872:
of the conjugate acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C
989:
1663:
1211:
96:
999:
1255:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1168:
1052:
693:
407:
138:
753:
709:
1913:
1863:
1689:
1180:
1040:
749:
677:
659:
184:
172:
673:
697:
1853:
1820:
1769:
1761:
1723:
1681:
1471:
1415:
1344:
1270:
1113:
1097:
1089:
1048:
1016:
1893:
1845:
1812:
1753:
1715:
1671:
1654:
1608:
1555:
1518:
1489:
1453:
1374:
1366:
1262:
1188:
1152:
831:
681:
484:
741:
378:
40:
1630:
905:
713:
313:
244:
148:
1667:
411:
286:
204:
782:
77:
1060:
1907:
1867:
929:
729:
535:
525:
275:
1693:
1576:
773:
737:
49:
1437:
1216:
1176:
1125:
1024:
1012:
913:
685:
1786:
701:
358:
1719:
1410:
1341:
The
Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications
1266:
1198:
is used in the manufacture of six commercial fungicides which are inhibitors of
1141:
847:
651:
68:
1897:
1849:
1816:
1378:
1757:
1457:
885:
512:
235:
1765:
1585:-pyrazole from hydrazones and/or ketones monitored by high resolution ESI-MS"
1493:
647:
1522:
1232:
1222:
1148:
1129:
1101:
1020:
933:
901:
881:
1773:
1685:
1542:-pyrazoles from chalcones and hydrazine under mechanochemical ball milling"
880:
with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are
733:
635:
1560:
1537:
1172:
1160:
1156:
1081:
1011:
The term pyrazole was given to this class of compounds by German
Chemist
921:
897:
643:
255:
17:
1809:
Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals
264:
1797:
Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J Med Chem 2014, 57, 5845.
1235:, another analogue, the nitrogen atom in position 1 replaced by oxygen.
345:
295:
1714:. Materials Horizons: From Nature to Nanomaterials. pp. 229–306.
1646:"alpha-Amino-beta-(pyrazolyl-N) propionic acid: a new amino-acid from
639:
1676:
1645:
1093:
851:
215:
1475:
1441:
1396:
781:
Except where otherwise noted, data are given for materials in their
631:
333:
1164:
1124:
1105:
827:
195:
171:
161:
1147:
In medicine, derivatives of pyrazole are widely used, including
769:
324:
1536:
Zhang, Ze; Tan, Ya-Jun; Wang, Chun-Shan; Wu, Hao-Hao (2014).
896:
Pyrazoles are synthesized by the reaction of α,β-unsaturated
745:
395:
76:
67:
48:
39:
1015:
in 1883. In a classical method developed by German chemist
540:
186 to 188 °C (367 to 370 °F; 459 to 461 K)
920:
Substituted pyrazoles are prepared by condensation of 1,3-
1196:
3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
530:
66 to 70 °C (151 to 158 °F; 339 to 343 K)
799:
1442:"Action of ethyl acetoacetate on phenylhydrazine. I"
854:
atoms and two adjacent nitrogen atoms, which are in
1316:"Dissociation constants of organic acids and bases"
1581:-catalyzed synthesis of azines and 3,5-diphenyl-1
1644:Noe, F. F.; Fowden, L.; Richmond, P. T. (1959).
357:
1409:Johnson, William S.; Highet, Robert J. (1963).
147:
1481:Berichte der deutschen chemischen Gesellschaft
1047:at high temperatures (~200 °C) to form a
8:
984:A wide variety of pyrazoles can be made so:
850:characterized by a 5-membered ring of three
1225:, structural analogue of pyrazole with two
998:
993:
988:
435:InChI=1S/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
410:
285:
243:
28:
1929:Substances discovered in the 19th century
1675:
1559:
1390:
1388:
445:InChI=1/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
377:
1705:
1703:
1245:
1019:in 1898, pyrazole was synthesized from
466:
431:
406:
263:
1626:
1615:
1589:Indian Journal of Chemistry, Section B
1476:"Pyrazol aus Acetylen und Diazomethan"
276:
1575:Lasri, Jamal; Ismail, Ali I. (2018).
1136:In 1959, the first natural pyrazole,
438:Key: WTKZEGDFNFYCGP-UHFFFAOYSA-N
223:
203:
7:
1746:Bioorganic & Medicinal Chemistry
1538:"One-pot synthesis of 3,5-diphenyl-1
1039:to form a class of ligands known as
884:(celebrex) and the anabolic steroid
448:Key: WTKZEGDFNFYCGP-UHFFFAOYAW
348:
332:
1339:Eicher, T.; Hauptmann, S. (2003).
1328:from the original on 12 July 2017.
25:
1606:Fowden; Noe; Ridd; White (1959).
1510:Journal of Heterocyclic Chemistry
1397:https://doi.org/10.1002/jhet.3155
858:. Pyrazole is a weak base, with p
1187:
1112:
1059:
912:
789:
601:
596:
591:
586:
502:
496:
928:-type reactions). For example,
785:(at 25 °C , 100 kPa).
1259:The Royal Society of Chemistry
1132:, a pyrazole-derived analgesic
1043:. Pyrazole itself reacts with
490:
1:
1140:, was isolated from seeds of
1108:is produced as a by-product.
1092:in the presence of elemental
1086:)-1,3-diphenylprop-2-en-1-one
117:1,2-Diazacyclopenta-2,4-diene
936:gives 3,5-dimethylpyrazole:
1844:. Wiley. pp. 363–395.
1811:. Wiley. pp. 405–425.
1720:10.1007/978-981-16-8399-2_7
1712:Nanostructured Biomaterials
1343:(2nd ed.). Wiley-VCH.
1267:10.1039/9781849733069-FP001
1080:-pyrazole is produced when
63:
35:
1945:
1898:10.2174/138527211796378497
1850:10.1002/9783527825158.ch11
1817:10.1002/9783527693931.ch31
1425:, vol. 4, p. 351
1379:10.2174/138527211795378263
1219:, fully saturated analogue
1031:Conversion to scorpionates
976:H + 2 H
826:is an organic compound of
1758:10.1016/j.bmc.2017.09.035
1458:10.1002/cber.188301602194
1229:-adjacent nitrogen atoms.
892:Preparation and reactions
779:
567:
562:
477:
457:
422:
131:
123:
111:
95:
90:
62:
34:
1842:Organofluorine Chemistry
1494:10.1002/cber.18980310363
1295:pubchem.ncbi.nlm.nih.gov
668:Precautionary statements
1523:10.1002/jhet.5570450231
1200:succinate dehydrogenase
1411:"3,5-Dimethylpyrazole"
1133:
81:
72:
53:
44:
1924:Simple aromatic rings
1261:. 2014. p. 141.
1128:
1045:potassium borohydride
1037:potassium borohydride
1035:Pyrazoles react with
113:Systematic IUPAC name
80:
71:
52:
43:
1577:"Metal-free and FeCl
1561:10.3987/COM-13-12867
1212:3,5-dimethylpyrazole
97:Preferred IUPAC name
1668:1959Natur.184...69B
1138:1-pyrazolyl-alanine
1121:Occurrence and uses
960: → (CH
520: g·mol
185:Beilstein Reference
31:
1648:Citrullus vulgaris
1472:von Pechmann, Hans
1446:Chemische Berichte
1134:
856:ortho-substitution
812:Infobox references
82:
73:
54:
45:
29:
1892:(16): 2897–2970.
1752:(21): 5891–5903.
1729:978-981-16-8398-5
1625:Missing or empty
1423:Collected Volumes
1416:Organic Syntheses
1276:978-0-85404-182-4
1104:in which case an
1098:sodium persulfate
1090:hydrazine hydrate
1049:tridentate ligand
1017:Hans von Pechmann
952: + N
820:Chemical compound
818:
817:
626:Hazard statements
391:CompTox Dashboard
173:Interactive image
86:
85:
58:
57:
16:(Redirected from
1936:
1901:
1872:
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1804:
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1789:
1784:
1778:
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1734:
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1707:
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1679:
1677:10.1038/184069a0
1641:
1635:
1634:
1628:
1623:
1621:
1613:
1609:Proc. Chem. Soc.
1603:
1597:
1596:
1572:
1566:
1565:
1563:
1533:
1527:
1526:
1504:
1498:
1497:
1488:(3): 2950–2951.
1468:
1462:
1461:
1434:
1428:
1426:
1419:
1406:
1400:
1392:
1383:
1382:
1373:(9): 1423–1463.
1367:Curr. Org. Chem.
1361:
1355:
1354:
1336:
1330:
1329:
1327:
1320:
1312:
1306:
1305:
1303:
1301:
1287:
1281:
1280:
1253:"Front Matter".
1250:
1191:
1153:COX-2 inhibitors
1116:
1100:, or by using a
1088:is reacted with
1063:
1002:
997:
992:
924:with hydrazine (
916:
802:
796:
793:
792:
775:
771:
767:
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747:
743:
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653:
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600:
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519:
504:
498:
492:
485:Chemical formula
415:
414:
399:
397:
381:
361:
350:
336:
314:Gmelin Reference
297:
289:
278:
267:
247:
227:
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151:
64:
36:
32:
21:
1944:
1943:
1939:
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1903:
1886:Curr. Org. Chem
1883:
1881:
1879:Further reading
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1709:
1708:
1701:
1662:(4688): 69–70.
1643:
1642:
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1009:
979:
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963:
959:
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951:
947:
943:
906:dehydrogenation
904:and subsequent
894:
879:
875:
871:
864:
845:
841:
837:
830:group with the
821:
814:
809:
808:
807: ?)
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106:
23:
22:
15:
12:
11:
5:
1942:
1940:
1932:
1931:
1926:
1921:
1919:Aromatic bases
1916:
1906:
1905:
1880:
1877:
1874:
1873:
1858:
1832:
1825:
1799:
1790:
1779:
1735:
1728:
1699:
1650:(water melon)"
1636:
1598:
1578:
1567:
1554:(1): 103–112.
1528:
1517:(2): 503–505.
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1220:
1214:
1207:
1204:
1193:
1192:
1122:
1119:
1118:
1117:
1076:3,5-Diphenyl-1
1073:
1068:3,5-Diphenyl-1
1066:
1065:
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1032:
1029:
1008:
1005:
1004:
1003:
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873:
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862:
843:
839:
835:
819:
816:
815:
810:
788:
787:
783:standard state
780:
777:
776:
726:P305+P354+P338
722:P305+P351+P338
671:
666:
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662:
629:
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1859:9783527347117
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1826:9783527339471
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1599:
1595:(3): 362–373.
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1495:
1491:
1487:
1484:(in German).
1483:
1482:
1477:
1473:
1467:
1464:
1459:
1455:
1452:: 2597–2599.
1451:
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1350:3-527-30720-6
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1257:. Cambridge:
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1203:
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1197:
1190:
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1185:
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1174:
1170:
1169:fenpyroximate
1166:
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1145:
1143:
1139:
1131:
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1120:
1115:
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931:
930:acetylacetone
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907:
903:
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1177:tebufenpyrad
1151:and similar
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1013:Ludwig Knorr
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132:Identifiers
124:Other names
102:
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1300:17 February
1181:tolfenpyrad
1142:watermelons
1041:scorpionate
848:heterocycle
846:H. It is a
612:Signal word
478:Properties
283:100.005.471
225:ChEMBL15967
205:CHEBI:17241
126:1,2-Diazole
1908:Categories
1291:"Pyrazole"
1240:References
886:stanozolol
581:Pictograms
513:Molar mass
379:3QD5KJZ7ZJ
236:ChemSpider
160:3D model (
139:CAS Number
1914:Pyrazoles
1868:234149806
1766:0968-0896
1438:Knorr, L.
1233:isoxazole
1223:imidazole
1149:celecoxib
1130:Celecoxib
1102:hydrazone
1072:-pyrazole
1053:Tp ligand
1051:known as
1021:acetylene
934:hydrazine
922:diketones
902:hydrazine
898:aldehydes
882:celecoxib
766:P403+P233
762:P362+P364
758:P361+P364
754:P337+P317
750:P332+P317
718:P304+P340
714:P302+P352
710:P301+P317
690:P264+P265
572:labelling
304:206-017-1
296:EC Number
105:-Pyrazole
30:Pyrazole
18:Pyrazoles
1774:28988624
1694:37499048
1686:13804343
1474:(1898).
1440:(1883).
1323:Archived
1206:See also
1173:fipronil
1161:betazole
1157:zaleplon
824:Pyrazole
563:Hazards
546:Basicity
256:DrugBank
149:288-13-1
1664:Bibcode
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865:11.5 (p
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469:c1cnc1
462:SMILES
334:C00481
216:ChEMBL
91:Names
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1690:S2CID
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828:azole
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319:1360
196:ChEBI
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