854:
816:
835:
286:
211:
66:
872:
471:
476:
42:
1430:
51:
587:
801:. It has proven to be a stable, easy-to-handle and effective oxidizing agent which is readily controllable by a suitable choice of the reaction conditions. It delivers oxidation products in an environmentally friendly manner and often in high yields especially in the presence of organic catalysts such as
741:
but the release at room temperature in the presence of catalysts proceeds in a controlled manner. Thus the compound is suitable as a safe substitute for the unstable aqueous solution of hydrogen peroxide. Because of the tendency for thermal decomposition, which accelerates at temperatures above
728:
Hydrogen peroxide–urea is a readily water-soluble, odorless, crystalline solid, which is available as white powder or colorless needles or platelets. Upon dissolving in various solvents, the 1:1 complex dissociates back to urea and hydrogen peroxide. So just like
689:
For the preparation of the complex, urea is dissolved in 30% hydrogen peroxide (molar ratio 2:3) at temperatures below 60 °C. upon cooling this solution, hydrogen peroxide–urea precipitates in the form of small platelets.
1270:
Varma, Rajender S.; Naicker, Kannan P. (1999). "The Urea−Hydrogen
Peroxide Complex: Solid-State Oxidative Protocols for Hydroxylated Aldehydes and Ketones (Dakin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles".
484:
451:
1401:
R.S. Varma, K.P. Naicker, "The Urea-Hydrogen
Peroxide Complex: Solid-State Oxidative Protocols for Hydroxylated Aldehydes and Ketones (Dakin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles",
1428:, V. Mascitti, K.F. McClure, M.J. Munchhof, R.P. Robinson, Jr., "4-(5-Cyano-pyrazol-1-yl)-piperidine derivatives as GPR 119 modulators", issued 2012-5-31, assigned to Pfizer Inc.
546:
1495:
M.Y. Rios; E. Salazar; H.F. Olivo (2007), "Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing urea–hydrogen peroxide in ethyl acetate",
1444:
D. Rong; V.A. Phillips; R.S. Rubio; M.A. Castro; R.T. Wheelhouse, "A safe, convenient and efficient method for the preparation of heterocyclic N-oxides using urea-hydrogen peroxide",
426:
879:
The oxygen atom transferred to the alkene originates from the peroxoimide acid formed intermediately from benzonitrile. The resulting imidic acid tautomerizes to the benzamide.
600:
766:
Hydrogen peroxide–urea is mainly used as a disinfecting and bleaching agent in cosmetics and pharmaceuticals. As a drug, this compound is used in some preparations for the
1212:
1636:
Halleux, Francis; Pons, Jean-François; Wilson, Ian; Simoens, Bart; Van Riet, Romuald; Lefebvre, Michel (2023). "Detonation performance of urea-hydrogen peroxide (UHP)".
986:
887:
The compound acts as a strong oxidizing agent and can cause skin irritation and severe eye damage. Urea–hydrogen peroxide was also found to be an insensitive
853:
325:
815:
834:
1022:
Yu, Lei; Meng, Bo; Huang, Xian (2008). "Urea-Hydrogen
Peroxide Complex: A Selective Oxidant in the Synthesis of 2-Phenylselenyl-1,3-butadienes".
526:
1228:
1517:
A. Watanabe; T. Uchida; K. Ito; T. Katsuki (2002), "Highly enantioselective Baeyer-Villiger oxidation using Zr(salen) complex as catalyst",
1709:
1232:
823:
It converts thiols selectively to disulfides, secondary alcohols to ketones, sulfides to sulfoxides and sulfones, nitriles to amides, and
1101:
1003:
1204:
861:
It oxidizes ketones to esters, in particular cyclic ketones, such as substituted cyclohexanones or cyclobutanones to give lactones (
300:
1471:
H. Heaney; A.J. Newbold (2001), "The oxidation of aromatic aldehydes by magnesium monoperoxyphthalate and urea-hydrogen peroxide",
657:-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an
871:
781:
Carbamide peroxide is also suitable as a disinfectant, e.g. for germ reduction on contact lens surfaces or as an antiseptic for
1297:
Harry Heaney, Francesca
Cardona, Andrea Goti, "Hydrogen Peroxide–Urea" Encyclopedia of Reagents for Organic Synthesis 2008.
1057:
Fritchie, C. J. Jr.; McMullan, R. K. (1981). "Neutron
Diffraction Study of the 1:1 Urea:Hydrogen Peroxide complex at 81 K".
862:
1674:
1319:"Urea-Hydrogen Peroxide (UHP) oxidation of thiols to the corresponding disulfides promoted by maleic anhydride as mediator"
1248:
538:
607:
1734:
1541:
L. Ji; Y.-N. Wang; C. Qian; X.-Z. Chen (2013), "Nitrile-promoted alkene epoxidation with urea-hydrogen peroxide (UHP)",
939:
C.-S. Lu; E.W. Hughes; P.A. Giguère (1941), "The crystal structure of the urea-hydrogen peroxide addition compound CO(NH
520:
243:
1160:
264:
1147:
1729:
1724:
802:
470:
694:
984:
Harald Jakob; Stefan
Leininger; Thomas Lehmann; Sylvia Jacobi; Sven Gutewort. "Peroxo Compounds, Inorganic".
701:
of 1:1. The compound is simply produced (on a scale of several hundred tonnes a year) by the dissolution of
868:
The epoxidation of various alkenes in the presence of benzonitrile yields oxiranes in yields of 79 to 96%.
475:
206:
1425:
905:
530:
498:
463:
88:
78:
1161:"A Clinical Evaluation of Carbamide Peroxide and Hydrogen Peroxide Whitening Agents during Daytime Use"
1704:
1571:
900:
722:
281:
148:
114:
770:. It is also used to relieve minor inflammation of gums, oral mucosal surfaces and lips including
1719:
1653:
1618:
1554:
1111:
1039:
1589:
Halleux, Francis; Pons, Jean-François; Wilson, Ian; Van Riet, Romuald; Lefebvre, Michel (2022).
1224:
65:
1699:
1519:
1473:
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999:
957:
843:
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706:
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1136:
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1478:
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1408:
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1280:
1172:
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1031:
991:
962:
809:
348:
252:
188:
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1236:
1208:
1201:
1123:
767:
710:
658:
542:
285:
210:
124:
1370:
168:
1714:
1344:
888:
847:
578:
569:
1590:
1528:
1482:
924:
1693:
1657:
1622:
698:
410:
199:
1558:
1318:
1176:
1043:
674:
534:
437:
432:
1302:
1188:
1093:
995:
232:
41:
17:
1550:
1455:
1084:
H. Heaney; F. Cardona; A. Goti; A.L. Frederick (2013). "Hydrogen
Peroxide-Urea".
742:
82 °C, it should not be heated above 60 °C, particularly in pure form.
828:
771:
553:
415:
75 to 91.5 °C (167.0 to 196.7 °F; 348.1 to 364.6 K) (decomposes)
1375:
8th
International Electronic Conference on Synthetic Organic Chemistry. ECSOC-8
1403:
1070:
1035:
379:
179:
782:
678:
670:
666:
504:
1649:
1606:
1353:
1184:
669:, it is used as a source of hydrogen peroxide when dissolved in water for
738:
512:
966:
850:) and give, under suitable conditions, the corresponding benzoic acids.
1371:"Microwave-assisted oxidation of alcohols using urea hydrogen peroxide"
797:
In the laboratory, it is used as a more easily handled replacement for
400:
219:
1614:
1412:
1284:
508:
50:
1504:
1334:
775:
734:
1159:
Mokhlis, G. R.; Matis, B. A.; Cochran, M. A.; Eckert, G. J. (2000).
577:
Except where otherwise noted, data are given for materials in their
1591:"Small-Scale Detonation of Industrial Urea-Hydrogen Peroxide (UHP)"
891:, capable of detonation by strong impulse under heavy confinement.
786:
654:
159:
147:
137:
721:
The solid state structure of this adduct has been determined by
702:
650:
1545:(in German), vol. 43, no. 16, pp. 2256–2264,
1523:(in German), vol. 43, no. 25, pp. 4481–4485,
1477:(in German), vol. 42, no. 37, pp. 6607–6609,
1450:(in German), vol. 49, no. 48, pp. 6933–6935,
1328:(in German), vol. 10, no. 10, pp. 1358–1363,
870:
852:
833:
814:
269:
49:
40:
1499:(in German), vol. 9, no. 5, pp. 459–462,
1407:(in German), vol. 1, no. 2, pp. 189–191,
595:
697:, hydrogen peroxide cocrystallizes with urea with the
745:
The solubility of commercial samples varies from 0.05
1317:
B. Karami; M. Montazerozohori; M. H. Habibi (2005),
774:
and dental irritation, and to emulsify and disperse
1225:
309:InChI=1S/CH4N2O.H2O2/c2-1(3)4;1-2/h(H4,2,3,4);1-2H
961:, vol. 63, no. 6, pp. 1507–1513,
231:
1249:"Ear Drops GENERIC NAME(S): CARBAMIDE PEROXIDE"
123:
1364:
1362:
1086:Encyclopedia of Reagents for Organic Synthesis
987:Ullmann's Encyclopedia of Industrial Chemistry
8:
1369:M. Lukasiewicz; D. Bogdal; J. Pielichowski.
1017:
1015:
1165:Journal of the American Dental Association
785:, ear drops or for superficial wounds and
284:
209:
187:
29:
1466:
1464:
1343:
1333:
1312:
1310:
979:
977:
975:
934:
932:
713:. The laboratory synthesis is analogous.
251:
1396:
1394:
1392:
1390:
916:
330:
305:
280:
1119:
1109:
842:Hydroxybenzaldehydes are converted to
838:Reaktionen von Methoxyphenolen mit UHP
200:
1638:Propellants, Explosives, Pyrotechnics
1595:Propellants, Explosives, Pyrotechnics
1229:University of Maryland Medical Center
558:60 °C (140 °F; 333 K)
312:Key: AQLJVWUFPCUVLO-UHFFFAOYSA-N
167:
7:
1675:"Hydrogen peroxide urea adduct, UHP"
436:
875:Epoxidierung von Cyclohexen mit UHP
222:
25:
1137:Sigma-Aldrich specification sheet
857:Baeyer-Villiger-Oxidation mit UHP
1059:Acta Crystallographica Section B
762:Disinfectant and bleaching agent
585:
474:
469:
363:
357:
102:Urea peroxide, percarbamide, UHP
64:
1177:10.14219/jada.archive.2000.0380
808:or inorganic catalysts such as
581:(at 25 °C , 100 kPa).
1683:"Carbamide Peroxide Monograph"
819:Reaktionen mit Carbamidperoxid
733:, the (erroneously) so-called
369:
354:
93:Peroxol–carbonyl diamide (1/1)
1:
1529:10.1016/S0040-4039(02)00831-6
1483:10.1016/S0040-4039(01)01332-6
1303:10.1002/047084289X.rh047.pub2
1094:10.1002/047084289X.rh047.pub3
996:10.1002/14356007.a19_177.pub2
645:composed of equal amounts of
1572:"Hydrogen peroxide urea SDS"
1551:10.1080/00397911.2012.699578
1456:10.1016/j.tetlet.2008.09.124
793:Reagent in organic synthesis
82:Hydrogen peroxide–urea (1/1)
1710:Cleaning product components
1677:. Organic Chemistry Portal.
36:
1751:
1235:October 18, 2007, at the
1071:10.1107/S0567740881005116
1036:10.1080/00397910802109224
863:Baeyer–Villiger oxidation
575:
450:
445:
419:
341:
321:
296:
107:
99:
87:
77:
72:
63:
35:
1426:WO patent 2012069948
1024:Synthetic Communications
717:Structure and properties
695:water of crystallization
653:. It contains solid and
521:Precautionary statements
1148:Chemicalland data sheet
990:. Weinheim: Wiley-VCH.
705:in excess concentrated
31:Hydrogen peroxide–urea
1650:10.1002/prep.202300011
1607:10.1002/prep.202100250
876:
858:
839:
820:
806:-butenedioic anhydride
709:solution, followed by
632:urea hydrogen peroxide
620:Hydrogen peroxide–urea
54:
45:
906:Peroxide-based bleach
874:
856:
837:
818:
749:g/mL to more than 0.6
89:Systematic IUPAC name
53:
44:
925:Sigma-Aldrich 289132
1735:Explosive chemicals
967:10.1021/ja01851a007
901:Sodium percarbonate
723:neutron diffraction
387: g·mol
32:
1576:merckmillipore.com
1207:2008-03-17 at the
877:
859:
840:
821:
768:whitening of teeth
663:carbamide peroxide
608:Infobox references
55:
46:
30:
18:Carbamide peroxide
1730:Hydrogen peroxide
1520:Tetrahedron Lett.
1474:Tetrahedron Lett.
1447:Tetrahedron Lett.
1413:10.1021/ol990522n
1285:10.1021/ol990522n
1213:UMD of New Jersey
1120:|periodical=
958:J. Am. Chem. Soc.
844:dihydroxybenzenes
827:-heterocycles to
799:hydrogen peroxide
731:hydrogen peroxide
707:hydrogen peroxide
647:hydrogen peroxide
643:chemical compound
640:crystalline solid
616:Chemical compound
614:
613:
564:Safety data sheet
499:Hazard statements
265:CompTox Dashboard
149:Interactive image
59:
58:
27:Chemical compound
16:(Redirected from
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711:crystallization
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661:. Often called
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1578:. 16 May 2023.
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1191:on 2013-02-23.
1171:(9): 1269–77.
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1705:Antiseptics
1497:Green Chem.
1065:(5): 1086.
783:mouthwashes
554:Flash point
485:Signal word
392:Appearance
342:Properties
207:100.004.275
169:CHEBI:75178
1694:Categories
1615:1826/17469
1404:Org. Lett.
1380:2016-05-10
1279:(2): 189.
912:References
685:Production
464:Pictograms
405:1.50 g/cm
380:Molar mass
333:O=C(N)N.OO
253:31PZ2VAU81
180:ChemSpider
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115:CAS Number
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