288:
169:
769:
35:
695:
463:
458:
44:
607:
878:) because the risk of explosion is far less. However, it is still considered as an explosive compound, decomposing above 65 °C. A respirator dust mask, protective gloves and safety glasses are recommended. Pyrolysis of AIBN without a trap for the formed 2-cyanopropyl radicals results in the formation of
676:. For example, they do not have oxygenated byproducts or much yellow discoloration. Additionally, they do not cause too much grafting and therefore are often used when making adhesives, acrylic fibers, detergents, etc.
471:
438:
996:
Overberger, C. G., O'Shaughnessy, M. T., Shalit, H. (1949). The
Preparation of Some Aliphatic Azo Nitriles and their Decomposition in Solution. Journal of the American Chemical Society, 71(8), 2661-2666.
708:
of 131 kJ/mol and results in two 2-cyano-2-propyl (carbon) radicals and a molecule of nitrogen gas. The release of nitrogen gas pushes this decomposition forward due to the increase in
1054:
620:
964:
704:. This happens at temperatures above 40 °C, but in experiments is more commonly done at temperatures between 66 °C and 72 °C. This decomposition has a Δ
337:
561:
517:
1007:
981:
118:
302:
657:. This white powder is soluble in alcohols and common organic solvents but is insoluble in water. It is often used as a foamer in
34:
553:
899:
557:
549:
745:
627:
511:
235:
1075:
721:
266:
462:
879:
176:
788:
gives the substituted dialkylhydrazine. In the second step, the hydrazine is oxidized to the azo derivative:
43:
911:
457:
565:
164:
1070:
768:
685:
521:
485:
450:
56:
741:
283:
781:
749:
694:
537:
84:
740:
upon addition of AIBN. Another example of a radical reaction that can be initiated by AIBN is the
581:
577:
529:
503:
1015:
755:
AIBN-derived radicals abstract a hydrogen from HBr to give a bromine radical, which can add to
541:
977:
875:
760:
701:
666:
969:
944:
935:
Giese, Bernd; Gröninger, Kay S. (1990). "1,3,4,6-TETRA-O-ACETYL-2-DEOXY-a-D-GLUCOPYRANOSE".
871:
729:
673:
647:
643:
573:
422:
360:
900:
https://polymerchemistry.nouryon.com/products-applications/acrylic-polymer-initiators/aibn/
585:
244:
1035:
525:
146:
60:
2,2′-Azobis(2-methylpropionitrile), 2-(azo(1-cyano-1-methylethyl))-2-methylpropane nitrile
287:
168:
94:
598:
1050:
700:
Because azobisisobutyronitrile readily gives off free radicals, it is often used as a
17:
1064:
672:
As an azo initiator, radicals resulting from AIBN have multiple benefits over common
411:
157:
589:
855:
744:
hydrohalogenation of alkenes. AIBN has also been used as the radical initiator for
533:
545:
208:
752:. The resulting tributyltin radical can be used for removal of a bromine atom.
383:
137:
973:
948:
785:
737:
255:
925:
Clayden, J., Greeves, N., & Warren, S. (2017). Organic chemistry. MTM.
912:
https://www.sigmaaldrich.com/catalog/product/aldrich/441090?lang=en®ion=US
1051:
SIDS Initial
Assessment Report for 2,2′-Azobis(2-methylpropionitrile)
748:. The AIBN-derived 2-cyano-2-propyl radical abstracts the hydrogen from
689:
658:
491:
733:
725:
709:
401:
195:
177:
756:
662:
597:
Except where otherwise noted, data are given for materials in their
495:
712:. And the 2-cyano-2-propyl radical is stabilized by the −CN group.
910:
2,2′-Azobis(2-methylpropionitrile) 441090. (n.d.). Retrieved from
499:
219:
117:
107:
898:
AIBN initiator and other azo initiators. (n.d.). Retrieved from
859:
724:
and other radical-induced reactions. For instance, a mixture of
720:
These radicals formed by the decomposition of AIBN can initiate
569:
271:
416:
103 to 105 °C (217 to 221 °F; 376 to 378 K)
311:
InChI=1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
321:
InChI=1/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
763:
of an alkene proceeds with anti-Markovnikov selectivity.
962:
Schirmann, Jean-Pierre; Bourdauducq, Paul. "Hydrazine".
615:
1055:
Organisation for
Economic Co-operation and Development
862:. Water-soluble azo initiators are also available.
207:
93:
965:Ullmann's Encyclopedia of Industrial Chemistry
8:
921:
919:
284:DTXSID70859108 DTXSID1026457, DTXSID70859108
692:gas to form two 2-cyanoprop-2-yl radicals:
684:In its most characteristic reaction, AIBN
286:
167:
145:
26:
243:
891:
342:
307:
282:
158:
314:Key: OZAIFHULBGXAKX-VAWYXSNFSA-N
7:
860:1,1′-azobis(cyclohexanecarbonitrile)
780:AIBN is produced in two steps from
324:Key: OZAIFHULBGXAKX-VAWYXSNFBT
198:
736:will react if heated, forming the
25:
767:
693:
605:
461:
456:
42:
33:
601:(at 25 °C , 100 kPa).
1:
688:, eliminating a molecule of
1036:Water-soluble Azo initiators
722:free-radical polymerizations
1092:
870:AIBN is safer to use than
858:behave similarly, such as
680:Mechanism of decomposition
388:164.21 g/mol
882:, which is highly toxic.
880:tetramethylsuccinonitrile
642:(abbreviated AIBN) is an
595:
437:
432:
353:
345:CC(C)(C#N)/N=N/C(C)(C)C#N
333:
298:
77:
65:
55:
50:
41:
32:
974:10.1002/14356007.a13_177
949:10.15227/orgsyn.069.0066
776:Production and analogues
746:Wohl–Ziegler bromination
512:Precautionary statements
997:doi:10.1021/ja01176a018
968:. Weinheim: Wiley-VCH.
28:Azobisisobutyronitrile
640:Azobisisobutyronitrile
70:Azobisisobutylonitrile
68:Azobisisobutyronitrile
18:Azobisisobutylonitrile
1008:"Vazo Product Grades"
782:acetone cyanohydrin
750:tributyltin hydride
423:Solubility in water
29:
1076:Radical initiators
716:Chemical reactions
628:Infobox references
27:
937:Organic Syntheses
876:radical initiator
761:hydrohalogenation
702:radical initiator
674:organic peroxides
667:radical initiator
636:Chemical compound
634:
633:
486:Hazard statements
267:CompTox Dashboard
119:Interactive image
16:(Redirected from
1083:
1038:
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1027:
1026:
1024:
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1014:. Archived from
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994:
988:
987:
959:
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952:
932:
926:
923:
914:
908:
902:
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872:benzoyl peroxide
784:. Reaction with
771:
742:anti-Markovnikov
730:maleic anhydride
697:
644:organic compound
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361:Chemical formula
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1012:www2.dupont.com
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837:
833:
829:
823:
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803:
799:
795:
778:
759:. This type of
718:
682:
656:
652:
637:
630:
625:
624:
623: ?)
614:
610:
606:
602:
514:
488:
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396:white crystals
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15:
12:
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5:
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1045:External links
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983:978-3527306732
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681:
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599:standard state
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134:
133:
130:
129:Abbreviations
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125:
123:
122:
114:
112:
105:
102:
101:
99:
98:
90:
88:
83:
80:
79:
75:
74:
67:
63:
62:
59:
53:
52:
48:
47:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1088:
1077:
1074:
1072:
1071:Azo compounds
1069:
1068:
1066:
1056:
1052:
1049:
1048:
1044:
1037:
1032:
1029:
1018:on 2009-03-26
1017:
1013:
1009:
1003:
1000:
993:
990:
985:
979:
975:
971:
967:
966:
958:
955:
950:
946:
942:
938:
931:
928:
922:
920:
916:
913:
907:
904:
901:
895:
892:
885:
883:
881:
877:
873:
865:
863:
861:
857:
856:azo compounds
850:+ 2 HCl
826:
800:C(CN)OH + N
791:
790:
789:
787:
783:
775:
770:
766:
765:
764:
762:
758:
753:
751:
747:
743:
739:
735:
731:
727:
723:
715:
713:
711:
707:
703:
698:
696:
691:
687:
679:
677:
675:
670:
668:
664:
660:
649:
645:
641:
629:
622:
617:
600:
594:
516:
513:
509:
508:
490:
487:
483:
482:
479:
476:
473:
469:
468:
464:
459:
455:
452:
448:
447:
443:
441:
436:
431:
427:
424:
420:
419:
415:
413:
412:Melting point
410:
409:
405:
403:
400:
399:
395:
392:
391:
387:
385:
382:
381:
365:
362:
358:
357:
352:
343:
339:
332:
318:
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304:
297:
289:
285:
281:
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233:
226:
225:
223:
221:
218:
217:
210:
206:
205:
203:
197:
193:
192:
185:
184:
182:
180:
175:
174:
170:
166:
163:
161:
159:ECHA InfoCard
156:
155:
148:
144:
143:
141:
139:
136:
135:
131:
128:
127:
120:
116:
115:
113:
109:
104:
103:
96:
92:
91:
89:
86:
82:
81:
76:
64:
58:
54:
49:
45:
40:
36:
31:
19:
1031:
1020:. Retrieved
1016:the original
1011:
1002:
992:
963:
957:
940:
936:
930:
906:
894:
869:
853:
779:
754:
719:
705:
699:
683:
671:
639:
638:
477:
439:
220:RTECS number
78:Identifiers
66:Other names
820:+ 2 H
472:Signal word
393:Appearance
354:Properties
165:100.001.030
1065:Categories
1022:2007-12-15
886:References
792:2 (CH
686:decomposes
451:Pictograms
384:Molar mass
260:3234 1325
245:FZ6PX8U5YB
138:ChemSpider
106:3D model (
85:CAS Number
57:IUPAC name
1053:from the
874:(another
786:hydrazine
738:copolymer
665:and as a
646:with the
578:P403+P235
574:P370+P378
562:P304+P340
558:P304+P312
554:P301+P312
442:labelling
406:1.1 g cm
256:UN number
227:UG0800000
186:201-132-3
178:EC Number
854:Related
690:nitrogen
659:plastics
433:Hazards
757:alkenes
734:toluene
726:styrene
710:entropy
648:formula
621:what is
619: (
478:Warning
402:Density
378:
196:PubChem
95:78-67-1
1057:(OECD)
980:
943:: 66.
866:Safety
663:rubber
616:verify
613:
338:SMILES
51:Names
842:→
838:+ Cl
428:poor
303:InChI
132:AIBN
108:JSmol
978:ISBN
808:→
728:and
661:and
590:P501
586:P420
582:P411
570:P330
566:P312
550:P280
546:P273
542:P271
538:P270
534:P264
530:P261
526:P234
522:P220
518:P210
504:H412
500:H332
496:H302
492:H242
236:UNII
209:6547
147:6299
72:AIBN
970:doi
945:doi
732:in
669:.
440:GHS
272:EPA
199:CID
1067::
1010:.
976:.
941:69
939:.
918:^
588:,
584:,
580:,
576:,
572:,
568:,
564:,
560:,
556:,
552:,
548:,
544:,
540:,
536:,
532:,
528:,
524:,
520:,
502:,
498:,
494:,
444::
372:12
1025:.
986:.
972::
951:.
947::
848:2
846:N
844:2
840:2
836:2
834:H
832:2
830:N
828:2
824:O
822:2
818:2
816:H
814:2
812:N
810:2
806:4
804:H
802:2
798:2
796:)
794:3
706:G
655:2
653:N
651:2
611:Y
376:4
374:N
370:H
368:8
366:C
274:)
270:(
110:)
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
