255:
162:
38:
725:
445:
28:
713:
535:
1525:
Liu, Hui; Tomooka, Craig S.; Xu, Simon L.; Yerxa, Benjamin R.; Sullivan, Robert W.; Xiong, Yifeng; Moore, Harold W. (1999). "Dimethyl
Squarate and ITS Conversion to 3-Ethenyl-4-Methoxycyclobutene-1,2-Dione and 2-Butyl-6-Ethenyl-5-Methoxy-1,4-Benzoquinone".
1323:
1021:(brown) is obtained together with the previous compound. It has a columnar structure including channels filled with water molecules; these can be removed and replaced without destroying the crystal structure. The chains are
453:
425:
1817:
Summerscales, Owen T.; Frey, Alistair S. P.; Cloke, F. Geoffrey N.; Hitchcock, Peter B. (2009). "Reductive disproportionation of carbon dioxide to carbonate and squarate products using a mixed-sandwich U(III) complex".
987:
atom, and the crystal structure consists of a cubic arrangement of hollow cells, whose walls are either six squarate anions (leaving a 7 Å wide void) or several water molecules (leaving a 5 Å void).
503:
1770:
Frey, Alistair S.; Cloke, F. Geoffrey N.; Hitchcock, Peter B. (2008). "Mechanistic
Studies on the Reductive Cyclooligomerisation of CO by U(III) Mixed Sandwich Complexes; the Molecular Structure of
1028:
Copper(II) squarate monomeric and dimeric mixed-ligand complexes were synthesized and characterized. Infrared, electronic and Q-Band EPR spectra as well as magnetic susceptibilities are reported.
507:
1690:
Hitoshi, Kumagai; Hideo, Sobukawa; Mohamedally, Kurmoo (2008). "Hydrothermal syntheses, structures and magnetic properties of coordination frameworks of divalent transition metals".
700:. Because the negative charges are equally distributed between each oxygen atom, the dianion of squaric acid is completely symmetrical (unlike squaric acid itself) with all C−C
548:
499:
742:
Many of the reactions of squaric acid involve the OH groups. The molecule behaves similarly to a strong dicarboxylic acid. It is stronger acid than typical carboxylic acids.
304:
1732:
Reinprecht, J. T.; Miller, J. G.; Vogel, G. C.; et al. (1979). "Synthesis and
Characterization of Copper(II) Squarate Complexes". Inorg. Chem., 19, 927-931
668:
Squaric acid is a white crystalline powder. The onset of thermal decomposition depends on the different thermodynamic conditions such as heating rates.
1742:
Park, J. D.; Cohen, S. & Lacher, J. R. (1962). "Hydrolysis
Reactions of Halogenated Cyclobutene Ethers: Synthesis of Diketocyclobutenediol".
1553:
Silverberg, Nanette B.; Lim, Joseph K.; Paller, Amy S.; Mancini, Anthony J. (2000). "Squaric acid immunotherapy for warts in children".
1369:
924:
920:
269:
1385:
Lee, K.-S.; Kweon, J. J.; Oh, I.-H.; Lee, C. E. (2012). "Polymorphic phase transition and thermal stability in squaric acid (
27:
491:
555:
1658:
Maier, Günther; Rohr, Christine (1995). "Ethynediol: Photochemical generation and matrix-spectroscopic identification".
657:
481:
212:
1623:
Ian Storer, R.; Aciro, Caroline; Jones, Lyn H. (2011). "Squaramides: Physical
Properties, Synthesis and Applications".
671:
The structure of squaric acid is not a perfect square, as the carbon–carbon bond lengths are not quite equal. The high
233:
991:
119:
1032:
386:
37:
958:
169:
1445:; Powell, David L. (1963). "New Aromatic Anions. III. Molecular Orbital Calculations on Oxygenated Anions".
1112:
495:
444:
157:
1854:
1307:
1063:
928:
865:
1869:
1473:
1442:
1025:; they are coupled antiferromagnetically in the hydrated form, ferromagnetically in the anhydrous form.
693:
467:
437:
910:
1699:
980:
57:
250:
85:
1859:
1715:
1507:
646:
487:
1864:
1831:
1799:
1744:
1640:
1605:
1570:
1447:
1365:
1823:
1791:
1752:
1707:
1667:
1632:
1597:
1562:
1535:
1499:
1455:
1424:
1357:
1289:
1285:
1093:
938:
871:
813:
582:
575:
327:
1588:
Yoshimasu, Takashi; Furukawa, Fukumi (2016). "Modified immunotherapy for alopecia areata".
221:
139:
1176:
875:
861:. They are displaced by diverse nucleophiles. In this way dithiosquarate can be prepared.
639:
95:
1703:
724:
254:
161:
1361:
1192:
650:
603:
526:
473:
622:; and the conjugate base of the hydrogensquarate anion is the divalent squarate anion
1848:
1511:
1311:
1160:
1124:
1022:
942:
858:
653:
376:
150:
1719:
1490:
Arthur H. Schmidt (1980). "Reaktionen von
Quadratsäure und Quadratsäure-Derivaten".
712:
1267:
578:
201:
1601:
1336:
1209:
1144:
1074:
882:
701:
514:
1428:
909:
One or both of the oxygen (=O) groups in the squarate anion can be replaced by
1711:
1671:
1225:
1067:
934:
888:
355:
130:
1539:
1566:
977:
1835:
1803:
1644:
1609:
1574:
1503:
1252:
1248:
1756:
1459:
1636:
1352:
Robert West (1980). "History of the
Oxocarbons". In Robert West (ed.).
954:
672:
188:
170:
1795:
881:
Diethyl squarate has been used as an intermediate in the synthesis of
1827:
1282:
984:
812:
The OH groups are labile in squaric acid. It forms a dichloride with
983:
and squaric acid in water at 200 °C. The water is bound to the
525:
Except where otherwise noted, data are given for materials in their
1256:
697:
118:
108:
927:, retain the aromatic character of squarate and have been called
957:, forming mono- and polynuclear complexes with hard metal ions.
574:
because its four carbon atoms approximately form a square, is a
891:
are prepared by displacement of alkoxy or chloride groups from
1474:"Acidity Tables for Heteroatom Organic Acids and Carbon Acids"
1111:
are obtainable by reductive coupling of carbon monoxide using
770:
676:
238:
36:
26:
1073:
Although impractical, squarate and related anions such as
1066:
to give 1,2-diethoxy-3,3,4,4-tetrafluoro-1-cyclobutene.
1062:
The original synthesis started with the ethanolysis of
543:
857:
The chlorides are good leaving groups, reminiscent of
864:
The bis(methylether) is prepared by alkylation with
381:> 300 °C (572 °F; 573 K)
200:
94:
1555:Journal of the American Academy of Dermatology
704:identical and all C−O bond lengths identical.
606:of squaric acid is the hydrogensquarate anion
8:
1337:3,4-Dihydroxy-3-cyclobutene-1,2-dione, 98+%
874:is used for the treatment of warts and for
642:, which consist only of carbon and oxygen.
1347:
1345:
253:
160:
138:
15:
220:
31:Structural formula (carbon atoms omitted)
1784:Journal of the American Chemical Society
1485:
1483:
1277:
1273:
1259:
1243:
1239:
1235:
1231:
1219:
1215:
1202:
1198:
1186:
1182:
1170:
1166:
1154:
1150:
1134:
1130:
1098:
1079:
1049:
1045:
1041:
1037:
1012:
1008:
1004:
1000:
996:
967:
963:
915:
902:
898:
894:
850:
846:
842:
838:
834:
830:
826:
822:
796:
792:
788:
784:
764:
760:
756:
752:
748:
730:Ball-and-stick model of the squarate ion
692:= 3.4 for the second is attributable to
625:
609:
595:
591:
587:
278:InChI=1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
1685:
1683:
1681:
1300:
309:
288:InChI=1/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
274:
249:
953:Squarate dianion behaves similarly to
519:190 °C (374 °F; 463 K)
151:
1308:3,4-Dihydroxy-3-cyclobutene-1,2-dione
281:Key: PWEBUXCTKOWPCW-UHFFFAOYSA-N
62:3,4-Dihydroxycyclobut-3-ene-1,2-dione
7:
941:at 10 K (−263 °C) affords
718:Squaric acid dianion resonance forms
976:(yellow, cubic) can be prepared by
291:Key: PWEBUXCTKOWPCW-UHFFFAOYAC
191:
1362:10.1016/B978-0-12-744580-9.50005-1
1251:analog of squaric acid, where the
14:
1356:. Academic Press. pp. 1–14.
925:1,3-bis(dicyanomethylene)squarate
921:1,2-bis(dicyanomethylene)squarate
1255:of squaric acid are replaced by
919:. The resulting anions, such as
723:
711:
685:= 1.5 for the first proton and p
533:
443:
339:
992:Cobalt(II) squarate dihydroxide
529:(at 25 °C , 100 kPa).
645:Squaric acid is a reagent for
345:
333:
1:
1033:iron(II) squarate dihydroxide
658:protein tyrosine phosphatases
1692:Journal of Materials Science
1602:10.1016/j.autrev.2016.02.021
649:, used for instance to make
959:Cobalt(II) squarate hydrate
22:
1886:
1429:10.1016/j.jpcs.2012.02.013
1712:10.1007/s10853-007-2033-8
1672:10.1002/jlac.199619960303
523:
424:
419:
371:white crystalline powder
320:
300:
265:
78:
68:
56:
51:
21:
1540:10.15227/orgsyn.076.0189
1070:gives the squaric acid.
482:Precautionary statements
1820:Chemical Communications
1567:10.1067/mjd.2000.103631
1324:"SICHERHEITSDATENBLATT"
1113:organouranium complexes
1031:The same method yields
929:pseudo-oxocarbon anions
694:resonance stabilization
949:Coordination complexes
866:trimethyl orthoformate
42:
32:
1417:J. Phys. Chem. Solids
937:of squaric acid in a
638:. This is one of the
73:Cyclobutenedioic acid
40:
30:
1590:Autoimmunity Reviews
1504:10.1055/s-1980-29291
1064:perfluorocyclobutene
981:cobalt(II) hydroxide
58:Preferred IUPAC name
41:Ball-and-stick-model
1790:(42): 13816–13817.
1757:10.1021/ja00874a015
1704:2008JMatS..43.2123K
1460:10.1021/ja00900a010
664:Chemical properties
363: g·mol
18:
1637:10.1039/c0cs00200c
939:solid argon matrix
656:and inhibitors of
647:chemical synthesis
556:Infobox references
312:c1(c(c(=O)c1=O)O)O
43:
33:
16:
1796:10.1021/ja8059792
1751:(15): 2919–2922.
1745:J. Am. Chem. Soc.
1528:Organic Syntheses
1454:(17): 2577–2579.
1448:J. Am. Chem. Soc.
564:Chemical compound
562:
561:
468:Hazard statements
234:CompTox Dashboard
120:Interactive image
47:
46:
1877:
1840:
1839:
1828:10.1039/b815576c
1814:
1808:
1807:
1767:
1761:
1760:
1739:
1733:
1730:
1724:
1723:
1698:(7): 2123–2130.
1687:
1676:
1675:
1655:
1649:
1648:
1631:(5): 2330–2346.
1620:
1614:
1613:
1585:
1579:
1578:
1550:
1544:
1543:
1522:
1516:
1515:
1487:
1478:
1477:
1470:
1464:
1463:
1439:
1433:
1432:
1414:
1413:
1412:
1404:
1403:
1395:
1394:
1382:
1376:
1375:
1349:
1340:
1334:
1328:
1327:
1326:. 21 March 2021.
1320:
1314:
1305:
1290:semisquaric acid
1280:
1262:
1246:
1222:
1206:
1189:
1173:
1157:
1141:
1137:
1110:
1109:
1108:
1105:
1094:acetylenediolate
1091:
1090:
1089:
1086:
1053:
1020:
975:
918:
911:dicyanomethylene
905:
876:alopecia areata
872:Dibutyl squarate
853:
814:thionyl chloride
800:
768:
727:
715:
640:oxocarbon anions
637:
636:
635:
632:
621:
620:
619:
616:
598:
583:chemical formula
546:
540:
537:
536:
509:
505:
501:
497:
493:
489:
475:
447:
362:
347:
341:
335:
328:Chemical formula
258:
257:
242:
240:
224:
204:
193:
172:
164:
153:
142:
122:
98:
23:
19:
1885:
1884:
1880:
1879:
1878:
1876:
1875:
1874:
1845:
1844:
1843:
1816:
1815:
1811:
1781:
1777:
1773:
1769:
1768:
1764:
1741:
1740:
1736:
1731:
1727:
1689:
1688:
1679:
1660:Liebigs Annalen
1657:
1656:
1652:
1622:
1621:
1617:
1587:
1586:
1582:
1552:
1551:
1547:
1524:
1523:
1519:
1489:
1488:
1481:
1472:
1471:
1467:
1441:
1440:
1436:
1411:
1408:
1407:
1406:
1402:
1399:
1398:
1397:
1393:
1390:
1389:
1388:
1386:
1384:
1383:
1379:
1372:
1351:
1350:
1343:
1335:
1331:
1322:
1321:
1317:
1306:
1302:
1298:
1279:
1275:
1271:
1261:
1257:
1245:
1241:
1237:
1233:
1229:
1221:
1217:
1213:
1204:
1200:
1196:
1188:
1184:
1180:
1177:Rhodizonic acid
1172:
1168:
1164:
1156:
1152:
1148:
1139:
1136:
1132:
1128:
1121:
1106:
1103:
1102:
1100:
1096:
1087:
1084:
1083:
1081:
1077:
1060:
1054:(light brown).
1051:
1047:
1043:
1039:
1035:
1018:
1014:
1010:
1006:
1002:
998:
994:
973:
969:
965:
961:
951:
917:
913:
904:
900:
896:
892:
852:
848:
844:
840:
836:
832:
828:
824:
820:
807:
798:
794:
790:
786:
782:
777:
766:
762:
758:
754:
750:
746:
740:
735:
734:
733:
732:
731:
728:
720:
719:
716:
691:
683:
666:
633:
630:
629:
627:
623:
617:
614:
613:
611:
607:
597:
593:
589:
585:
565:
558:
553:
552:
551: ?)
542:
538:
534:
530:
484:
470:
456:
440:
414:
407:
405:
395:
360:
350:
344:
338:
330:
316:
313:
308:
307:
296:
293:
292:
289:
283:
282:
279:
273:
272:
261:
243:
236:
227:
207:
194:
182:
145:
125:
112:
101:
88:
74:
72:
64:
63:
12:
11:
5:
1883:
1881:
1873:
1872:
1867:
1862:
1857:
1847:
1846:
1842:
1841:
1822:(2): 198–200.
1809:
1779:
1775:
1771:
1762:
1734:
1725:
1677:
1666:(3): 307–309.
1650:
1625:Chem. Soc. Rev
1615:
1596:(7): 664–667.
1580:
1561:(5): 803–808.
1545:
1517:
1479:
1465:
1434:
1423:(7): 890–895.
1409:
1400:
1391:
1377:
1370:
1341:
1329:
1315:
1299:
1297:
1294:
1293:
1292:
1265:
1223:
1207:
1193:Cyclopropenone
1190:
1174:
1158:
1142:
1120:
1117:
1059:
1056:
1016:
971:
950:
947:
906:(X = OR, Cl).
859:acid chlorides
855:
854:
849:+ 2 HCl + 2 SO
810:
809:
805:
791:(OH)] → [C
780:
775:
739:
736:
729:
722:
721:
717:
710:
709:
708:
707:
706:
689:
681:
665:
662:
654:squaraine dyes
651:photosensitive
604:conjugate base
572:quadratic acid
570:, also called
563:
560:
559:
554:
532:
531:
527:standard state
524:
521:
520:
517:
511:
510:
508:P305+P351+P338
504:P304+P340+P310
500:P303+P361+P353
496:P301+P330+P331
485:
480:
477:
476:
471:
466:
463:
462:
457:
452:
449:
448:
441:
436:
433:
432:
422:
421:
417:
416:
412:
403:
397:
393:
383:
382:
379:
373:
372:
369:
365:
364:
358:
352:
351:
348:
342:
336:
331:
326:
323:
322:
318:
317:
315:
314:
311:
303:
302:
301:
298:
297:
295:
294:
290:
287:
286:
284:
280:
277:
276:
268:
267:
266:
263:
262:
260:
259:
246:
244:
232:
229:
228:
226:
225:
217:
215:
209:
208:
206:
205:
197:
195:
187:
184:
183:
181:
180:
176:
174:
166:
165:
155:
147:
146:
144:
143:
135:
133:
127:
126:
124:
123:
115:
113:
106:
103:
102:
100:
99:
91:
89:
84:
81:
80:
76:
75:
71:Quadratic acid
70:
66:
65:
61:
60:
54:
53:
49:
48:
45:
44:
34:
13:
10:
9:
6:
4:
3:
2:
1882:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1855:Organic acids
1853:
1852:
1850:
1837:
1833:
1829:
1825:
1821:
1813:
1810:
1805:
1801:
1797:
1793:
1789:
1785:
1766:
1763:
1758:
1754:
1750:
1747:
1746:
1738:
1735:
1729:
1726:
1721:
1717:
1713:
1709:
1705:
1701:
1697:
1693:
1686:
1684:
1682:
1678:
1673:
1669:
1665:
1661:
1654:
1651:
1646:
1642:
1638:
1634:
1630:
1626:
1619:
1616:
1611:
1607:
1603:
1599:
1595:
1591:
1584:
1581:
1576:
1572:
1568:
1564:
1560:
1556:
1549:
1546:
1541:
1537:
1533:
1529:
1521:
1518:
1513:
1509:
1505:
1501:
1497:
1493:
1486:
1484:
1480:
1475:
1469:
1466:
1461:
1457:
1453:
1450:
1449:
1444:
1438:
1435:
1430:
1426:
1422:
1418:
1381:
1378:
1373:
1371:9780127445809
1367:
1363:
1359:
1355:
1348:
1346:
1342:
1338:
1333:
1330:
1325:
1319:
1316:
1313:
1312:Sigma-Aldrich
1309:
1304:
1301:
1295:
1291:
1287:
1284:
1269:
1266:
1264:
1254:
1250:
1227:
1224:
1211:
1208:
1194:
1191:
1178:
1175:
1162:
1161:Croconic acid
1159:
1146:
1143:
1126:
1125:Acetylenediol
1123:
1122:
1118:
1116:
1114:
1095:
1076:
1071:
1069:
1065:
1057:
1055:
1034:
1029:
1026:
1024:
1023:ferromagnetic
993:
989:
986:
982:
979:
960:
956:
948:
946:
944:
943:acetylenediol
940:
936:
932:
930:
926:
922:
912:
907:
890:
886:
884:
879:
877:
873:
869:
867:
862:
860:
819:
818:
817:
815:
804:
781:
778:
774:
745:
744:
743:
737:
726:
714:
705:
703:
699:
695:
688:
684:
680:
674:
669:
663:
661:
659:
655:
652:
648:
643:
641:
605:
600:
584:
580:
577:
573:
569:
557:
550:
545:
528:
522:
518:
516:
513:
512:
486:
483:
479:
478:
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377:Melting point
375:
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359:
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332:
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152:ECHA InfoCard
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39:
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25:
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17:Squaric acid
1870:Cyclobutenes
1819:
1812:
1787:
1783:
1765:
1748:
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1737:
1728:
1695:
1691:
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1491:
1468:
1451:
1446:
1443:West, Robert
1437:
1420:
1416:
1380:
1353:
1339:. Alfa Aesar
1332:
1318:
1303:
1268:Moniliformin
1072:
1061:
1030:
1027:
990:
952:
933:
908:
887:
880:
870:
863:
856:
811:
802:
772:
741:
702:bond lengths
686:
678:
670:
667:
644:
601:
579:organic acid
571:
568:Squaric acid
567:
566:
459:
426:
409:
400:
390:
79:Identifiers
69:Other names
1498:(12): 961.
1210:Cyclobutene
1145:Deltic acid
978:autoclaving
889:Squaramides
883:perzinfotel
738:Derivatives
515:Flash point
454:Signal word
368:Appearance
321:Properties
158:100.018.875
1849:Categories
1354:Oxocarbons
1296:References
1226:Squaramide
1068:Hydrolysis
935:Photolysis
438:Pictograms
356:Molar mass
222:SVR9D0VODW
131:ChemSpider
107:3D model (
86:CAS Number
1860:Diketones
1512:101871124
1492:Synthesis
1253:OH groups
1140:HO−C≡C−OH
1058:Synthesis
970:)·2H
767:(OH)] + H
581:with the
429:labelling
179:220-761-4
171:EC Number
96:2892-51-5
1865:Enediols
1836:19099067
1804:18817397
1774:(μ-η:η-C
1720:95205908
1645:21399835
1610:26932732
1575:10775858
1249:nitrogen
1119:See also
1015:·3H
833:+ 2 SOCl
759:→ [C
576:diprotic
420:Hazards
1700:Bibcode
1534:: 189.
1075:deltate
955:oxalate
696:of the
673:acidity
549:what is
547: (
387:Acidity
361:114.056
189:PubChem
1834:
1802:
1718:
1643:
1608:
1573:
1510:
1368:
1283:sodium
1281:, the
1263:groups
985:cobalt
914:=C(CN)
783:[C
544:verify
541:
460:Danger
415:= 3.4
305:SMILES
52:Names
1716:S2CID
1508:S2CID
808:= 3.5
799:] + H
779:= 1.5
698:anion
675:with
406:= 1.5
270:InChI
202:17913
140:16919
109:JSmol
1832:PMID
1800:PMID
1782:)".
1664:1996
1641:PMID
1606:PMID
1571:PMID
1496:1980
1415:)".
1366:ISBN
1286:salt
1247:, a
1185:(CO)
1169:(CO)
1153:(CO)
1133:(CO)
1092:and
1040:(OH)
999:(OH)
962:Co(C
923:and
829:(OH)
755:(OH)
602:The
594:(OH)
492:P280
488:P260
474:H314
213:UNII
1824:doi
1792:doi
1788:130
1753:doi
1708:doi
1668:doi
1633:doi
1598:doi
1563:doi
1536:doi
1500:doi
1456:doi
1425:doi
1358:doi
1288:of
1272:NaC
1238:(NH
1138:or
837:→ C
801:, p
427:GHS
239:EPA
192:CID
1851::
1830:.
1798:.
1786:.
1749:84
1714:.
1706:.
1696:43
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1639:.
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1532:76
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1421:73
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1364:.
1344:^
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1276:HO
1270:,
1258:NH
1228:,
1212:,
1195:,
1179:,
1163:,
1147:,
1127:,
1115:.
1104:2−
1085:2−
1044:(C
1036:Fe
1003:(C
995:Co
945:.
931:.
885:.
878:.
868:.
845:Cl
816::
806:a2
776:a1
769:,
690:a2
682:a1
660:.
631:2−
608:HC
599:.
506:,
502:,
498:,
494:,
490:,
431::
413:a2
404:a1
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389:(p
1838:.
1826::
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1776:2
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1612:.
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1542:.
1538::
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1476:.
1462:.
1458::
1431:.
1427::
1410:4
1405:O
1401:4
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1392:2
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1374:.
1360::
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1260:2
1244:2
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1240:2
1236:2
1234:O
1232:4
1230:C
1220:6
1218:H
1216:4
1214:C
1205:O
1203:2
1201:H
1199:3
1197:C
1187:6
1183:2
1181:H
1171:5
1167:2
1165:H
1155:3
1151:2
1149:H
1135:2
1131:2
1129:H
1107:2
1101:O
1099:2
1097:C
1088:3
1082:O
1080:3
1078:C
1052:)
1050:4
1048:O
1046:4
1042:2
1038:2
1019:O
1017:2
1013:2
1011:)
1009:4
1007:O
1005:4
1001:2
997:3
974:O
972:2
968:4
966:O
964:4
916:2
903:2
901:X
899:2
897:O
895:4
893:C
851:2
847:2
843:2
841:O
839:4
835:2
831:2
827:2
825:O
823:4
821:C
803:K
797:4
795:O
793:4
789:3
787:O
785:4
773:K
771:p
765:3
763:O
761:4
757:2
753:2
751:O
749:4
747:C
687:K
679:K
677:p
634:4
628:O
626:4
624:C
618:4
615:−
612:O
610:4
596:2
592:2
590:O
588:4
586:C
539:Y
410:K
408:p
401:K
399:p
394:a
391:K
349:4
346:O
343:2
340:H
337:4
334:C
241:)
237:(
111:)
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