232:
139:
24:
406:
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414:
381:
807:
Trifluoracetone is also used in a synthesis of 2-trifluoromethyl-7-azaindoles starting with 2,6-dihalopyridines. The derived chiral imine is used to prepare enantiopure α-trifluoromethyl alanines and diamines by a
932:
Mello, Rossella; Martínez-Ferrer, Jaime; Asensio, Gregorio; González-Núñez, María Elena (2007). "Oppenauer
Oxidation of Secondary Alcohols with 1,1,1-Trifluoroacetone as Hydride Acceptor".
271:
866:
Günter
Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick (2002). "Fluorine Compounds, Organic".
841:
460:
916:
883:
1008:
246:
1018:
969:"Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols by the Strecker-type reaction"
770:
Hydrogenation of trifluoroacetone over platinum catalyst gives trifluoroisopropanol. The reduction can also be achieved
501:
454:
189:
210:
405:
472:
993:
146:
771:
96:
400:
134:
767:
and more electrophilic than acetone itself. Unlike both of those ketones, trifluoroacetone is prochiral.
713:
549:
428:
393:
717:
36:
801:
227:
62:
464:
476:
950:
912:
879:
821:
809:
764:
116:
1013:
942:
904:
871:
775:
763:
Many studies report on the reactions of trifluoroacetone. It is less prone to hydrate than
545:
294:
198:
627:
231:
138:
72:
778:
provides a route to tertiary alcohols. Alkylation and arylation can be achieved using
521:
495:
23:
968:
1002:
934:
553:
434:
366:
356:
127:
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908:
533:
325:
107:
875:
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790:
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346:
165:
147:
946:
438:
468:
494:
Except where otherwise noted, data are given for materials in their
899:
Prakash, G. K.Surya; Wang, Fang (2011). "1,1,1-Trifluoroacetone".
794:
95:
85:
215:
720:
gives the ketone according to this idealized equation:
812:
followed by either nitrile hydrolysis or reduction.
177:
71:
901:Encyclopedia of Reagents for Organic Synthesis
868:Ullmann's Encyclopedia of Industrial Chemistry
371:21–24 °C (70–75 °F; 294–297 K)
8:
789:Trifluoroacetone has been converted to the
544:Trifluoroacetone is produced from trifluoro
861:
859:
626:Hydrolysis of the keto-ester, followed by
532:. The compound is a colorless liquid with
230:
137:
115:
15:
197:
750:
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730:
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548:, which is generated by condensation of
833:
361:−78 °C (−108 °F; 195 K)
276:
251:
226:
488:−30 °C (−22 °F; 243 K)
128:
524:compound with the chemical formula CF
258:Key: FHUDAMLDXFJHJE-UHFFFAOYSA-N
7:
255:InChI=1S/C3H3F3O/c1-2(7)3(4,5)6/h1H3
800:It serves as an oxidizing agent in
168:
14:
404:
399:
312:
306:
22:
498:(at 25 °C , 100 kPa).
774:. Similarly, alkylation with
318:
300:
1:
540:Preparation, reactions, uses
842:"1,1,1-Trifluoracetone 95%"
712:Alternatively, addition of
41:1,1,1-Trifluoropropan-2-one
1035:
909:10.1002/047084289X.rn01348
630:affords trifluoroacetone:
1009:Trifluoromethyl compounds
492:
380:
375:
287:
267:
242:
55:
47:
35:
30:
21:
876:10.1002/14356007.a11_349
455:Precautionary statements
1019:Trifluoromethyl ketones
870:. Weinheim: Wiley-VCH.
17:1,1,1-Trifluoroacetone
782:anions and arenes/AlCl
714:methylmagnesium iodide
550:ethyl trifluoroacetate
518:1,1,1-trifluoroacetone
718:trifluoroacetic acid
50:Trifluoracetone, TFA
37:Preferred IUPAC name
802:Oppenauer oxidation
333: g·mol
18:
971:. sigmaaldrich.com
502:Infobox references
16:
947:10.1021/jo7016422
941:(72): 9376–9378.
918:978-0-471-93623-7
885:978-3-527-30673-2
822:Hexafluoroacetone
810:Strecker reaction
776:Grignard reagents
765:hexafluoroacetone
510:Chemical compound
508:
507:
429:Hazard statements
341:Colorless liquid
211:CompTox Dashboard
97:Interactive image
1026:
981:
980:
978:
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786:, respectively.
754:
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622:
546:acetoacetic acid
514:Trifluoroacetone
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470:
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332:
320:
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295:Chemical formula
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119:
99:
75:
26:
19:
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628:decarboxylation
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988:External links
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772:asymmetrically
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522:organofluorine
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682:
633:
632:
631:
629:
559:
558:
557:
555:
554:ethyl acetate
551:
547:
539:
537:
536:-like odour.
535:
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367:Boiling point
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357:Melting point
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228:DTXSID9059963
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129:ECHA InfoCard
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994:Safety sheet
973:. Retrieved
963:
938:
933:
927:
900:
894:
867:
846:. Retrieved
844:. dk.vwr.com
836:
806:
799:
788:
769:
762:
737:MgI → CF
711:
625:
543:
517:
513:
512:
420:
382:
56:Identifiers
48:Other names
484:Flash point
415:Signal word
351:1.252 g/mL
338:Appearance
288:Properties
135:100.006.370
1003:Categories
828:References
696:H → CF
659:O → CF
534:chloroform
394:Pictograms
326:Molar mass
199:K987U5C2CX
108:ChemSpider
84:3D model (
63:CAS Number
791:dioxirane
759:Reactions
733:H + 2 CH
385:labelling
156:207-005-9
148:EC Number
955:17975928
816:See also
780:malonate
520:) is an
376:Hazards
117:21111803
73:421-50-1
1014:Ketones
671:H + C
347:Density
331:112.051
166:PubChem
975:6 June
953:
915:
882:
848:6 June
793:using
753:+ MgO
741:C(O)CH
700:C(O)CH
688:C(O)CH
663:C(O)CH
639:C(O)CH
597:C(O)CH
593:→ CF
528:C(O)CH
421:Danger
272:SMILES
31:Names
795:oxone
749:+ CH
745:+ MgI
577:+ CH
247:InChI
86:JSmol
977:2017
951:PMID
913:ISBN
880:ISBN
850:2017
704:+ CO
655:+ H
613:+ C
552:and
477:P351
473:P338
469:P303
465:P261
461:P210
447:H335
443:H319
439:H315
435:H224
190:UNII
179:9871
943:doi
905:doi
872:doi
716:to
383:GHS
216:EPA
169:CID
1005::
949:.
939:24
911:.
903:.
878:.
858:^
804:.
797:.
729:CO
725:CF
692:CO
684:CF
679:OH
667:CO
643:CO
635:CF
621:OH
601:CO
581:CO
565:CO
561:CF
556::
475:,
471:,
467:,
463:,
445:,
441:,
437:,
387::
979:.
957:.
945::
921:.
907::
888:.
874::
852:.
784:3
751:4
747:2
743:3
739:3
735:3
731:2
727:3
706:2
702:3
698:3
694:2
690:2
686:3
677:5
675:H
673:2
669:2
665:2
661:3
657:2
653:5
651:H
649:2
647:C
645:2
641:2
637:3
619:5
617:H
615:2
611:5
609:H
607:2
605:C
603:2
599:2
595:3
591:5
589:H
587:2
585:C
583:2
579:3
575:5
573:H
571:2
569:C
567:2
563:3
530:3
526:3
516:(
319:O
316:3
313:F
310:3
307:H
304:3
301:C
218:)
214:(
88:)
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