37:
50:
758:
256:
183:
467:
472:
24:
664:
617:
480:
447:
36:
49:
566:
677:
558:
305:
562:
518:
1011:
949:
Stucky, G. D.; Rundle, R. E. (1963). "The
Structure of Phenylmagnesium Bromide Diethyletherate and the Nature of Grignard Reagents".
270:
796:
Coordinating solvents such as ether or THF, are required to solvate (complex) the magnesium(II) center. The solvent must be
428:
550:
684:
512:
23:
234:
888:. It can abstract even mildly acidic protons, thus the substrate must be protected where necessary. It often adds to
866:. The Mg–O distances are 201 and 206 pm whereas the Mg–C and Mg–Br distances are 220 pm and 244 pm, respectively.
404:
1016:
190:
642:
530:
466:
757:
726:
554:
397:
471:
178:
897:
538:
494:
459:
62:
570:
120:
801:
251:
86:
526:
901:
586:
542:
983:
951:
929:
638:
611:
160:
959:
885:
875:
738:
646:
582:
376:
328:
574:
289:
InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H
797:
778:
734:
393:
96:
578:
255:
182:
140:
804:
and water contain an acidic proton and thus react with phenylmagnesium bromide to give
655:
504:
1005:
813:
774:
730:
634:
171:
594:
893:
782:
762:
546:
500:
222:
862:
ligands from the ether or THF solvent. Thus, the Mg is tetrahedral and obeys the
978:
925:
881:
601:
863:
522:
387:
347:
151:
889:
786:
766:
722:
534:
963:
926:"Grignard Synthesis: Synthesis of Benzoic Acid and of Triphenylmethanol"
809:
805:
746:
365:
209:
191:
892:, such as ketones, aldehydes. With carbon dioxide, it reacts to give
847:
790:
742:
654:
Except where otherwise noted, data are given for materials in their
773:
Phenylmagnesium bromide is commercially available as solutions of
756:
131:
119:
109:
846:, the molecule is more complex. The compound invariably forms an
793:
may be used to activate the magnesium to initiate the reaction.
590:
896:
after an acidic workup. If three equivalents are reacted with
824:
Although phenylmagnesium bromide is routinely represented as
239:
789:
metal, usually in the form of turnings. A small amount of
279:
InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1
672:
741:. It is often used as a synthetic equivalent for the
761:Phenylmagnesium bromide is prepared by reaction of
729:. It is commercially available as a solution in
221:
95:
8:
919:
917:
781:. Laboratory preparation involves treating
254:
181:
159:
15:
816:, are also incompatible with the reagent.
808:. Carbonyl-containing solvents, such as
977:Bachmann, W. E.; Hetzner, H. P. (1955).
913:
310:
275:
250:
606:−45 °C (−49 °F; 228 K)
172:
282:Key: ANRQGKOBLBYXFM-UHFFFAOYSA-M
139:
7:
880:Phenylmagnesium bromide is a strong
737:(THF). Phenylmagnesium bromide is a
292:Key: ANRQGKOBLBYXFM-ZAQPMBKGAV
212:
14:
662:
470:
465:
48:
35:
22:
924:Robertson, D. L. (2007-01-03).
658:(at 25 °C , 100 kPa).
392:3.0M in diethyl ether, 1.0M in
699:, with the simplified formula
429:Occupational safety and health
1:
74:PMB, (bromomagnesio)benzene
1033:
993:, vol. 3, p. 839
873:
352:181.31 g mol
42:Complex with diethyl ether
1012:Organomagnesium compounds
652:
623:
446:
426:
421:
321:
301:
266:
79:
71:
61:
56:
47:
34:
21:
643:Methylmagnesium chloride
513:Precautionary statements
66:Bromido(phenyl)magnesium
17:Phenylmagnesium bromide
727:organometallic compound
697:Phenylmagnesium bromide
898:phosphorus trichloride
770:
760:
884:as well as a strong
442:flammable, volatile
417:45 (conjugate acid)
979:"Triphenylcarbinol"
964:10.1021/ja00890a039
377:Solubility in water
360:Colorless crystals
29:Complex with ethers
18:
902:triphenylphosphine
771:
685:Infobox references
624:Related compounds
382:Reacts with water
16:
991:Collected Volumes
984:Organic Syntheses
952:J. Am. Chem. Soc.
930:MiraCosta College
693:Chemical compound
691:
690:
639:Magnesium bromide
630:Related compounds
612:Safety data sheet
495:Hazard statements
235:CompTox Dashboard
121:Interactive image
1024:
1017:Phenyl compounds
996:
994:
987:
974:
968:
967:
958:(7): 1002–1003.
946:
940:
939:
937:
936:
921:
876:Grignard reagent
861:
860:
859:
845:
843:
842:
834:
833:
739:Grignard reagent
720:
718:
717:
709:
708:
675:
669:
666:
665:
647:Dibutylmagnesium
596:
592:
588:
584:
580:
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572:
568:
564:
560:
556:
552:
548:
544:
540:
536:
532:
528:
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506:
502:
474:
469:
329:Chemical formula
259:
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193:
185:
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163:
143:
123:
99:
52:
39:
26:
19:
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1021:
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1001:
1000:
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989:
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948:
947:
943:
934:
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872:
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854:
853:
851:
841:
838:
837:
836:
832:
829:
828:
827:
825:
822:
755:
735:tetrahydrofuran
716:
713:
712:
711:
707:
704:
703:
702:
700:
694:
687:
682:
681:
680: ?)
671:
667:
663:
659:
645:
641:
637:
631:
515:
497:
483:
462:
439:
413:
379:
341:
337:
331:
317:
314:
309:
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280:
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215:
203:
166:
146:
126:
113:
102:
89:
75:
67:
43:
40:
30:
27:
12:
11:
5:
1030:
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1020:
1019:
1014:
1004:
1003:
998:
997:
969:
941:
912:
911:
909:
906:
874:Main article:
871:
868:
856:
839:
830:
821:
818:
754:
751:
714:
705:
692:
689:
688:
683:
661:
660:
656:standard state
653:
650:
649:
632:
629:
626:
625:
621:
620:
615:
608:
607:
604:
598:
597:
567:P305+P351+P338
559:P303+P361+P353
555:P301+P330+P331
516:
511:
508:
507:
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493:
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489:
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136:
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107:
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100:
92:
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68:
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54:
53:
45:
44:
41:
32:
31:
28:
13:
10:
9:
6:
4:
3:
2:
1029:
1018:
1015:
1013:
1010:
1009:
1007:
992:
986:
985:
980:
973:
970:
965:
961:
957:
954:
953:
945:
942:
931:
927:
920:
918:
914:
907:
905:
904:can be made.
903:
899:
895:
891:
887:
883:
877:
869:
867:
865:
849:
819:
817:
815:
814:ethyl acetate
811:
807:
803:
799:
794:
792:
788:
784:
780:
776:
775:diethyl ether
768:
764:
759:
752:
750:
748:
744:
740:
736:
732:
731:diethyl ether
728:
724:
698:
686:
679:
674:
657:
651:
648:
644:
640:
636:
635:Phenyllithium
633:
628:
627:
622:
619:
618:External MSDS
616:
613:
610:
609:
605:
603:
600:
599:
517:
514:
510:
509:
499:
496:
492:
491:
488:
485:
482:
478:
477:
473:
468:
464:
461:
457:
456:
452:
450:
445:
441:
436:
435:
431:
430:
425:
420:
416:
410:
406:
403:
402:
399:
395:
391:
389:
386:
385:
381:
378:
374:
373:
369:
367:
364:
363:
359:
356:
355:
351:
349:
346:
345:
333:
330:
326:
325:
320:
311:
307:
300:
286:
276:
272:
265:
257:
253:
252:DTXSID3059214
249:
248:
246:
236:
232:
231:
224:
220:
219:
217:
211:
207:
206:
199:
198:
196:
194:
189:
188:
184:
180:
177:
175:
173:ECHA InfoCard
170:
169:
162:
158:
157:
155:
153:
150:
149:
142:
138:
137:
135:
133:
130:
129:
122:
118:
117:
115:
111:
106:
105:
98:
94:
93:
91:
88:
84:
83:
78:
70:
64:
60:
55:
51:
46:
38:
33:
25:
20:
990:
982:
972:
955:
950:
944:
933:. Retrieved
894:benzoic acid
879:
823:
795:
783:bromobenzene
772:
763:bromobenzene
725:-containing
696:
695:
486:
448:
438:Main hazards
427:
408:
80:Identifiers
72:Other names
882:nucleophile
753:Preparation
602:Flash point
481:Signal word
432:(OHS/OSH):
357:Appearance
342:MgBr
322:Properties
179:100.002.607
141:CHEBI:51238
1006:Categories
935:2008-01-25
908:References
864:octet rule
460:Pictograms
396:, 2.9M in
388:Solubility
370:1.14 g cm
348:Molar mass
313:Brc1ccccc1
152:ChemSpider
108:3D model (
87:CAS Number
63:IUPAC name
890:carbonyls
870:Chemistry
850:with two
820:Structure
787:magnesium
767:magnesium
723:magnesium
587:P403+P235
583:P370+P378
563:P304+P340
451:labelling
200:202-867-2
192:EC Number
802:alcohols
422:Hazards
161:10254417
97:100-58-3
810:acetone
806:benzene
798:aprotic
747:synthon
721:, is a
678:what is
676: (
405:Acidity
398:2Me-THF
366:Density
210:PubChem
848:adduct
800:since
791:iodine
769:metal.
743:phenyl
673:verify
670:
614:(SDS)
487:Danger
306:SMILES
57:Names
785:with
765:with
745:"Ph"
271:InChI
223:66852
132:ChEBI
110:JSmol
886:base
844:MgBr
812:and
719:MgBr
595:P501
591:P405
579:P363
575:P321
571:P310
551:P280
547:P264
543:P260
539:P243
535:P242
531:P241
527:P240
523:P233
519:P210
505:H314
501:H225
960:doi
779:THF
777:or
733:or
449:GHS
394:THF
240:EPA
213:CID
1008::
988:;
981:.
956:85
928:.
916:^
900:,
852:OR
749:.
593:,
589:,
585:,
581:,
577:,
573:,
569:,
565:,
561:,
557:,
553:,
549:,
545:,
541:,
537:,
533:,
529:,
525:,
521:,
503:,
453::
414:)
407:(p
995:.
966:.
962::
938:.
857:2
840:5
835:H
831:6
826:C
715:5
710:H
706:6
701:C
668:N
412:a
409:K
340:5
338:H
336:6
334:C
242:)
238:(
112:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
