223:
148:
574:: S-C = 186, C-N = 130, and S-O = 149 pm. The sulfur center is pyramidal. The C-S bond length is more similar to that of a single bond. For comparison, the C=S bond in thiourea is 171 pm. The long C-S bond indicates the absence of C=S character. Instead the bonding is described with a significant contribution from a dipolar resonance structure with multiple bonding between C and N. One consequence of this bonding is the planarity of the nitrogen centers. In the presence of water or
402:
397:
387:
392:
594:
33:
510:
24:
1101:
Hebeish, A.; El-Rafie, M. H.; Waly, A.; Moursi, A. Z. (1978). "Graft copolymerization of vinyl monomers onto modified cotton. IX. Hydrogen peroxide–thiourea dioxide redox system induced grafting of 2-methyl-5-vinylpyridine onto oxidized celluloses".
1071:
410:
367:
988:
Barnett first prepared thiourea dioxide ("aminoiminomethanesulphinic acid") by oxidizing thiourea ("thiocarbamide") with hydrogen peroxide ("hydrogen dioxide"). See: Barnett, Edward de Barry (1910)
833:
480:
1084:
Rábai, G.; Wang, R. T.; Kustin, Kenneth (1993). "Kinetics and mechanism of the oxidation of thiourea by chlorine dioxide" International
Journal of Chemical Kinetics. Volume 25: 53–62.
517:
775:
740:
992:
262:
1198:
1039:
Hoffmann, Michael; Edwards, John O. (1977). "Kinetics and
Mechanism of the Oxidation of Thiourea and N,N'-dialkylthioureas by Hydrogen Peroxide".
1131:"Chemoselective reduction of carbonyl groups of aromatic nitro carbonyl compounds to the corresponding nitroalcohols using thiourea dioxide"
819:
761:
237:
563:
The structure of thiourea dioxide depends on its environment. Crystalline and gaseous thiourea dioxide adopts a structure with C
476:
524:
462:
180:
401:
201:
396:
454:
105:
1193:
386:
1178:
989:
391:
143:
544:
424:
379:
1066:
955:
917:
868:
669:. It has been found that at pH values of less than 2, thiourea and hydrogen peroxide react to form a
484:
45:
472:
218:
71:
1183:
971:
803:
657:
The mechanism of the oxidation has been examined. An aqueous solution of thiourea dioxide has a
430:
1188:
946:
Makarov, S. V. (2001). "Recent Trends in the
Chemistry of Sulfur-Containing Reducing Agents".
825:
815:
767:
757:
618:
1152:
1142:
1111:
1085:
1048:
1023:
963:
925:
876:
807:
749:
682:
606:
Thiourea dioxide was first prepared in 1910 by the
English chemist Edward de Barry Barnett.
351:
285:
488:
189:
125:
996:
896:
Chen, I-C.; Wang, Y. (1984). "Reinvestigation of the
Structure of Thiourea S,S-Dioxide, CH
666:
597:
Structure of the sulfinic acid tautomer of thiourea dioxide, as exists in aqueous solution
81:
1069:, James H. Young, "PRODUCTION OF FORMAMIDINE SULFINIC ACID", issued 1957-2-26
222:
147:
959:
921:
872:
567:
552:
501:
468:
1172:
1157:
975:
583:
340:
136:
967:
492:
169:
1147:
1130:
799:
Gardner's
Commercially Important Chemicals: Synonyms, Trade Names, and Properties
797:
735:
571:
450:
1115:
593:
59:
Thiourea dioxide, DegaFAS, Reducing Agent F, Depilor, Formamidine
Sulfinic Acid
929:
881:
856:
686:
319:
116:
1027:
753:
829:
771:
745:
698:
670:
610:
811:
1089:
32:
710:
614:
579:
442:
1052:
1129:
Sambher, Shikha; Baskar, Chinnappan; Dhillon, Ranjit S. (22 May 2009).
714:
702:
678:
548:
156:
438:
500:
Except where otherwise noted, data are given for materials in their
434:
706:
592:
446:
104:
94:
23:
662:
575:
685:. The quality of the product can be assessed by titration with
206:
674:
658:
857:"The Crystal and Molecular Structure of Thiourea Dioxide"
681:. It can also be prepared by oxidation of thiourea with
661:
about 6.5 at which thiourea dioxide is hydrolyzed to
990:"The action of hydrogen dioxide on thiocarbamides,"
590:N)HN=CS(O)(OH), named formamidine sulfinic acid.
555:. It is a white solid, and exhibits tautomerism.
1018:D. Schubart "Sulfinic Acids and Derivatives" in
673:species. It is therefore convenient to keep the
168:
246:InChI=1S/CH4N2O2S/c2-1(3)6(4)5/h(H3,2,3)(H,4,5)
80:
1020:Ullmann's Encyclopedia of Industrial Chemistry
741:Ullmann's Encyclopedia of Industrial Chemistry
705:. Thiourea dioxide has also been used for the
1000:Journal of the Chemical Society, Transactions
677:between 3 and 5 and the temperature below 10
8:
855:Sullivan, R. A. L.; Hargreaves, A. (1962).
221:
146:
124:
15:
1156:
1146:
941:
939:
880:
188:
726:
267:
242:
217:
697:Thiourea dioxide is used in reductive
345:126 °C (259 °F; 399 K)
137:
1014:
1012:
249:Key: FYOWZTWVYZOZSI-UHFFFAOYSA-N
7:
796:Milne, George W. A. (11 July 2005).
609:Thiourea dioxide is prepared by the
578:, thiourea dioxide converts to the
159:
1199:Substances discovered in the 1910s
1104:Journal of Applied Polymer Science
14:
836:from the original on 18 June 2022
508:
400:
395:
390:
385:
300:
294:
50:Amino(imino)methanesulfinic acid
31:
22:
968:10.1070/RC2001v070n10ABEH000659
778:from the original on 2022-06-18
504:(at 25 °C , 100 kPa).
312:
306:
291:
1:
1022:, 2012, Wiley-VCH, Weinheim.
1148:10.3998/ark.5550190.0010.a14
802:. Hoboken, New Jersey, USA:
551:industry. It functions as a
1215:
1116:10.1002/app.1978.070220709
1158:2027/spo.5550190.0010.a14
930:10.1107/S010827018401012X
882:10.1107/S0365110X62001851
498:
366:
361:
278:
258:
233:
64:
56:
44:
39:
30:
21:
1028:10.1002/14356007.a25_461
948:Russian Chemical Reviews
754:10.1002/14356007.a26_227
713:nitroaldehydes and nitro
463:Precautionary statements
734:Fischer, Klaus (2003).
910:Acta Crystallographica
861:Acta Crystallographica
812:10.1002/0471736627.ch1
598:
1090:10.1002/kin.550250106
1067:US patent 2783272
736:"Textile Auxiliaries"
596:
545:organosulfur compound
547:that is used in the
46:Preferred IUPAC name
1053:10.1021/ic50178a069
1041:Inorganic Chemistry
960:2001RuCRv..70..885M
922:1984AcCrC..40.1937C
873:1962AcCry..15..675S
352:Solubility in water
327: g·mol
18:
995:2020-06-06 at the
804:Wiley-Interscience
717:to nitroalcohols.
599:
525:Infobox references
16:
1047:(12): 3333–3338.
916:(11): 1937–1938.
619:hydrogen peroxide
533:Chemical compound
531:
530:
425:Hazard statements
202:CompTox Dashboard
106:Interactive image
17:Thiourea dioxide
1206:
1163:
1162:
1160:
1150:
1126:
1120:
1119:
1110:(7): 1853–1866.
1098:
1092:
1082:
1076:
1075:
1074:
1070:
1063:
1057:
1056:
1036:
1030:
1016:
1007:
986:
980:
979:
943:
934:
933:
893:
887:
886:
884:
852:
846:
845:
843:
841:
793:
787:
786:
784:
783:
731:
683:chlorine dioxide
537:Thiourea dioxide
515:
512:
511:
494:
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486:
482:
478:
474:
470:
456:
452:
448:
444:
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436:
432:
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394:
389:
326:
314:
308:
302:
296:
293:
286:Chemical formula
226:
225:
210:
208:
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172:
161:
150:
139:
128:
108:
84:
35:
26:
19:
1214:
1213:
1209:
1208:
1207:
1205:
1204:
1203:
1194:Reducing agents
1169:
1168:
1167:
1166:
1141:(10): 141–145.
1128:
1127:
1123:
1100:
1099:
1095:
1083:
1079:
1072:
1065:
1064:
1060:
1038:
1037:
1033:
1017:
1010:
997:Wayback Machine
987:
983:
954:(10): 885–895.
945:
944:
937:
907:
903:
899:
895:
894:
890:
854:
853:
849:
839:
837:
822:
795:
794:
790:
781:
779:
764:
733:
732:
728:
723:
695:
667:sulfoxylic acid
652:
648:
644:
640:
636:
632:
628:
604:
589:
566:
561:
534:
527:
522:
521:
520: ?)
513:
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505:
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413:
382:
354:
324:
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274:
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111:
98:
87:
74:
60:
52:
51:
12:
11:
5:
1212:
1210:
1202:
1201:
1196:
1191:
1186:
1181:
1179:Sulfinic acids
1171:
1170:
1165:
1164:
1121:
1093:
1077:
1058:
1031:
1008:
1006: : 63–65.
981:
935:
905:
901:
897:
888:
867:(7): 675–682.
847:
820:
788:
762:
725:
724:
722:
719:
694:
691:
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630:
626:
603:
600:
587:
564:
560:
557:
553:reducing agent
532:
529:
528:
523:
507:
506:
502:standard state
499:
496:
495:
481:P305+P351+P338
466:
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419:
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328:
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316:
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309:
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289:
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280:
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273:
272:
270:C(=N)(N)S(=O)O
269:
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3:
2:
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827:
823:
821:9780471735182
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763:9783527303854
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668:
664:
660:
624:
623:
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591:
585:
584:sulfinic acid
581:
577:
573:
569:
558:
556:
554:
550:
546:
542:
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519:
503:
497:
467:
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398:
393:
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372:
370:
365:
360:
357:3.0 g/100 mL
356:
353:
349:
348:
344:
342:
341:Melting point
339:
338:
335:White powder
334:
331:
330:
323:
321:
318:
317:
290:
287:
283:
282:
277:
268:
264:
257:
243:
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219:DTXSID4029224
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138:ECHA InfoCard
135:
134:
127:
123:
122:
120:
118:
115:
114:
107:
103:
102:
100:
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25:
20:
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1003:
999:
984:
951:
947:
913:
909:
891:
864:
860:
850:
838:. Retrieved
798:
791:
780:. Retrieved
744:. Weinheim:
739:
729:
696:
656:
608:
605:
572:bond lengths
562:
540:
536:
535:
416:
368:
65:Identifiers
57:Other names
570:. Selected
411:Signal word
332:Appearance
279:Properties
144:100.015.598
1173:Categories
782:2022-06-18
721:References
380:Pictograms
320:Molar mass
190:42BWR07L73
117:ChemSpider
93:3D model (
72:CAS Number
1184:Thioureas
976:250741549
746:Wiley-VCH
707:reduction
699:bleaching
671:disulfide
641:→ (NH)(NH
611:oxidation
602:Synthesis
559:Structure
469:P235+P410
371:labelling
82:1758-73-2
1189:Amidines
993:Archived
834:Archived
830:57392953
776:Archived
772:55738480
711:aromatic
703:textiles
615:thiourea
580:tautomer
568:symmetry
362:Hazards
1135:Arkivoc
956:Bibcode
918:Bibcode
869:Bibcode
840:18 June
715:ketones
633:CS + 2H
549:textile
518:what is
516: (
157:PubChem
1073:
974:
828:
818:
770:
760:
687:indigo
649:H + 2H
543:is an
417:Danger
325:108.12
263:SMILES
40:Names
972:S2CID
617:with
541:thiox
238:InChI
170:61274
126:55213
95:JSmol
1139:2009
908:S".
842:2022
826:OCLC
816:ISBN
768:OCLC
758:ISBN
693:Uses
665:and
663:urea
645:)CSO
586:, (H
582:, a
576:DMSO
493:P501
489:P407
485:P310
477:P280
473:P270
455:H373
451:H335
447:H332
443:H318
439:H315
435:H302
431:H252
181:UNII
1153:hdl
1143:doi
1112:doi
1086:doi
1049:doi
1024:doi
964:doi
926:doi
877:doi
808:doi
750:doi
709:of
701:in
625:(NH
613:of
539:or
369:GHS
207:EPA
160:CID
1175::
1151:.
1137:.
1133:.
1108:22
1106:.
1045:16
1043:.
1011:^
1004:97
1002:,
970:.
962:.
952:70
950:.
938:^
924:.
914:40
912:.
875:.
865:15
863:.
859:.
832:.
824:.
814:.
806:.
774:.
766:.
756:.
748:.
738:.
689:.
679:°C
675:pH
659:pH
621:.
565:2v
491:,
487:,
483:,
479:,
475:,
471:,
453:,
449:,
445:,
441:,
437:,
433:,
373::
1161:.
1155::
1145::
1118:.
1114::
1088::
1055:.
1051::
1026::
978:.
966::
958::
932:.
928::
920::
906:2
904:O
902:2
900:N
898:4
885:.
879::
871::
844:.
810::
785:.
752::
653:O
651:2
647:2
643:2
639:2
637:O
635:2
631:2
629:)
627:2
588:2
514:N
313:S
310:2
307:O
304:2
301:N
298:4
295:H
292:C
209:)
205:(
97:)
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