576:
672:
20:
211:
structure. The reactivity of the B−H bonds depends on the other ligands. Electron-releasing ethyl groups as in triethylborohydride render the B−H center highly nucleophilic. In contrast, cyanoborohydride is a weaker reductant owing to the electron-withdrawing cyano substituent. The countercation also
901:
Schlesinger, H. C.; Brown, H. R.; Hoekstra, L. R. (1953). "Reactions of
Diborane with Alkali Metal Hydrides and Their Addition Compounds. New Syntheses of Borohydrides. Sodium and Potassium Borohydrides".
1125:
Jensen, J. A.; Gozum, J. E.; Pollina, D. M.; Girolami, G. S. (1988). "Titanium, Zirconium, and
Hafnium tetrahydroborates as "tailored" CVD precursors for metal diboride thin films".
994:
Jaroń, Tomasz; Wegner, Wojciech; Grochala, Wojciech (17 August 2018). "M and M2Li (M = Rb, Cs): new borohydride derivatives of yttrium and their hydrogen storage properties".
815:
485:
Sodium borohydride is the borohydride that is produced on the largest scale industrially, estimated at 5000 tons/year in 2002. The main use is for the reduction of
767:
Metal diborides find uses as coatings because of their hardness, high melting point, strength, resistance to wear and corrosion, and good electrical conductivity.
531:
Dithionite is used to bleach wood pulp. Sodium borohydride is also used to reduce aldehydes and ketones in the production of pharmaceuticals including
1077:
945:
567:, challenges are associated with slow kinetics and low yields of hydrogen as well as problems with regeneration of the parent borohydrides.
978:
832:
127:, but other salts are well known (see Table). Tetrahydroborates are also of academic and industrial interest in inorganic chemistry.
1056:
Besora, M.; Lledós, A. (2008). "Coordination Modes and
Hydride Exchange Dynamics in Transition Metal Tetrahydroborate Complexes".
1154:
600:, the borohydride ion is bound to the metal by means of one to three bridging hydrogen atoms. In most such compounds, the
441:
92:
139:
689:
559:
Because of their high hydrogen content, borohydride complexes and salts have been of interest in the context of
360:
1169:
937:
661:
597:
579:
23:
575:
961:
Hutchins, Robert O.; Hutchins, MaryGail K.; Crawley, Matthew L. (2007). "Sodium
Cyanoborohydride".
617:
280:
120:
693:
322:
124:
671:
1073:
1011:
974:
941:
828:
665:
490:
116:
1134:
1102:
1065:
1038:
1003:
966:
929:
911:
883:
856:
820:
703:
560:
192:
143:
80:
874:
Schlesinger, H. C.; Brown, H. R. (1940). "Metallo
Borohydrides. III. Lithium Borohydride".
58:, and its salts. Borohydride or hydroborate is also the term used for compounds containing
1174:
783:
532:
271:
623:
Metal borohydride complexes can often be prepared by a simple salt elimination reaction:
688:. When the borohydride complex is volatile, this decomposition pathway is the basis of
564:
486:
112:
1163:
637:
257:
860:
19:
536:
135:
970:
548:
208:
613:
824:
675:
Beryllium borohydride compound that creates a three center two electron bond.
609:
540:
1106:
1015:
1069:
544:
249:
155:
46:
1138:
1042:
915:
887:
1007:
308:
692:(CVD), a way of depositing thin films of metal borides. For example,
685:
712:
can be prepared through CVD of the zirconium(IV) tetrahydroborate
670:
574:
204:
43:
18:
684:
Some metal tetrahydroborates transform on heating to give metal
1093:
Franz, H.; Fusstetter, H.; Nöth, H. (1976). "Borohydride".
203:
In the borohydride anion and most of its modifications,
616:borohydride complexes are volatile. One example is
1029:Marks, T. J.; Kolb, J. R. (1977). "Borohydride".
216:Selected properties of various borohydride salts
16:Any chemical compound having a borohydride anion
963:Encyclopedia of Reagents for Organic Synthesis
816:Ullmann's Encyclopedia of Industrial Chemistry
212:influences the reducing power of the reagent.
138:borohydrides were first described in 1940 by
8:
813:Rittmeyer, P.; Wietelmann, U. "Hydrides".
1120:
1118:
1116:
846:
844:
808:
806:
804:
551:, as well as many flavorings and aromas.
760:
756:
752:
748:
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719:
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653:
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523:
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363:
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214:
182:
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149:
106:
102:
98:
86:
68:
61:
49:
29:
775:
146:. They synthesized lithium borohydride
79:is an integer from 0 to 3, for example
851:Makhaev, V. D. (2000). "Borohydride".
119:. The most important borohydrides are
191:Current methods involve reduction of
7:
187:, where M = Li, Na, K, Rb, Cs, etc.
14:
723:and hafnium(IV) tetrahydroborate
563:. Reminiscent of related work on
111:. Borohydrides find wide use as
861:10.1070/RC2000v069n09ABEH000580
26:of the tetrahydroborate anion,
275:(g/100 mL at 25 °C)
1:
971:10.1002/047084289X.rs059.pub2
474:high (supplied commercially)
245:(g/100 mL at 25 °C)
267:(g/100 mL, 25 °C)
253:(g/100 mL, 25 °C)
1191:
140:Hermann Irving Schlesinger
965:. John Wiley & Sons.
934:Chemistry of the Elements
932:; Earnshaw, Alan (1997).
690:chemical vapor deposition
825:10.1002/14356007.a13_199
1155:Sodium Tetrahydroborate
819:. Weinheim: Wiley-VCH.
381:240 with decomposition
95:or triethylhydroborate
83:or cyanotrihydroborate
54:, which is also called
1107:10.1002/zaac.654270202
676:
598:coordination complexes
593:
571:Coordination complexes
555:Potential applications
34:
1058:Structure and Bonding
938:Butterworth-Heinemann
930:Greenwood, Norman N.
674:
662:Beryllium borohydride
644:(solvent) → Ti[BH
578:
349:16.4 (at 20 °C)
195:with sodium hydride.
22:
1095:Z. Anorg. Allg. Chem
1070:10.1007/430_2007_076
580:Ball-and-stick model
355:0.1 (at 20 °C)
40:refers to the anion
24:Ball-and-stick model
1139:10.1021/ja00213a058
1043:10.1021/cr60306a004
996:Dalton Transactions
916:10.1021/ja01097a053
888:10.1021/ja01869a039
618:uranium borohydride
243:Solubility in water
217:
121:lithium borohydride
93:triethylborohydride
1008:10.1039/C3DT33048F
784:"Tetrahydroborate"
694:zirconium diboride
677:
594:
307:decomposes (44 in
215:
125:sodium borohydride
56:tetrahydridoborate
35:
1079:978-3-540-78633-7
947:978-0-08-037941-8
882:(12): 3429–3435.
502:] + 8 NaOH + 8 SO
491:sodium dithionite
478:
477:
117:organic synthesis
1182:
1143:
1142:
1133:(5): 1643–1644.
1127:J. Am. Chem. Soc
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936:(2nd ed.).
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904:J. Am. Chem. Soc
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876:J. Am. Chem. Soc
871:
865:
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853:Russ. Chem. Rev.
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839:
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799:
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733:
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704:hafnium diboride
701:
657:
607:
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561:hydrogen storage
527:
448:
423:
404:
367:
329:
287:
264:
230:Hydrogen density
225:molecular weight
218:
193:trimethyl borate
186:
167:
153:
144:Herbert C. Brown
110:
90:
81:cyanoborohydride
74:
53:
33:
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1002:(19): 6886–93.
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855:(69): 727–746.
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533:chloramphenicol
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113:reducing agents
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1149:External links
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1021:
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980:978-0471936237
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834:978-3527306732
833:
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788:Chemspider.com
774:
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769:
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565:ammonia borane
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487:sulfur dioxide
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687:
680:Decomposition
679:
673:
669:
667:
663:
643:
632:+ 4 Li[BH
626:
625:
624:
621:
619:
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611:
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238:melting point
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114:
94:
82:
78:
71:
65:
57:
48:
45:
39:
25:
21:
1170:Borohydrides
1130:
1126:
1098:
1094:
1088:
1061:
1057:
1051:
1034:
1030:
1024:
999:
995:
989:
962:
956:
933:
924:
907:
903:
896:
879:
875:
869:
852:
814:
791:. Retrieved
787:
778:
766:
683:
660:
622:
595:
558:
537:thiophenicol
530:
484:
202:
190:
181:→ 2 M[BH
136:Alkali metal
134:
76:
69:
63:
55:
37:
36:
1064:: 149–202.
910:: 199–204.
793:26 February
549:scopolamine
468:decomposes
465:decomposes
443:Li[BHEt
417:585 (under
221:Borohydride
209:tetrahedral
38:Borohydride
1164:Categories
1101:: 97–113.
771:References
656:O + 4 LiCl
614:homoleptic
608:ligand is
436:insoluble
433:insoluble
430:insoluble
390:insoluble
384:tolerated
352:insoluble
97:[BH(CH
1031:Chem. Rev
725:Hf[BH
714:Zr[BH
610:bidentate
584:Zr[BH
541:vitamin A
498:Na[BH
362:Na[BH
324:Na[BH
282:Li[BH
199:Structure
148:Li[BH
1016:23503711
739:M[BH
652:·Et
545:atropine
489:to give
462:unknown
459:unknown
399:K[BH
173:2 MH + B
156:diborane
75:, where
1037:: 263.
686:borides
666:dimeric
612:. Some
602:[BH
596:In its
453:105.94
233:Density
227:(g/mol)
131:History
85:[BH
60:[BH
28:[BH
1175:Anions
1076:
1014:
977:
944:
831:
547:, and
518:+ NaBO
506:→ 4 Na
408:53.94
372:62.84
334:37.83
292:21.78
235:(g/cm)
207:has a
759:+ 5 H
522:+ 6 H
456:0.95
414:1.17
378:1.20
366:(CN)]
340:1.07
337:10.6
317:22.5
304:20.9
298:0.66
295:18.5
205:boron
154:from
89:(CN)]
42:[
1074:ISBN
1012:PMID
975:ISBN
942:ISBN
829:ISBN
795:2013
747:→ MB
702:and
636:] +
628:TiCl
481:Uses
471:N/A
411:7.4
387:217
375:6.4
343:505
314:4.3
309:EtOH
301:280
250:MeOH
240:(°C)
142:and
123:and
91:and
1135:doi
1131:110
1103:doi
1099:427
1066:doi
1062:130
1039:doi
1004:doi
967:doi
912:doi
884:doi
857:doi
821:doi
751:+ B
707:HfB
697:ZrB
664:is
582:of
427:19
393:36
346:55
272:THF
115:in
1166::
1129:.
1115:^
1097:.
1072:.
1060:.
1035:77
1033:.
1010:.
1000:42
998:.
973:.
940:.
908:75
906:.
880:62
878:.
843:^
827:.
803:^
786:.
734::
668:.
638:Et
620:.
543:,
539:,
535:,
493::
424:)
311:)
259:Et
168::
101:CH
62:4−
1141:.
1137::
1109:.
1105::
1082:.
1068::
1045:.
1041::
1018:.
1006::
983:.
969::
950:.
918:.
914::
890:.
886::
863:.
859::
837:.
823::
797:.
761:2
757:6
755:H
753:2
749:2
745:4
743:]
741:4
731:4
729:]
727:4
720:4
718:]
716:4
709:2
699:2
654:2
650:4
648:]
646:4
642:O
640:2
634:4
630:4
606:]
604:4
590:4
588:]
586:4
526:O
524:2
520:2
516:4
514:O
512:2
510:S
508:2
504:2
500:4
447:]
445:3
421:2
419:H
403:]
401:4
364:3
328:]
326:4
286:]
284:4
263:O
261:2
185:]
183:4
179:6
177:H
175:2
165:6
163:H
161:2
159:B
152:]
150:4
109:]
107:3
105:)
103:3
99:2
87:3
77:n
73:]
70:n
67:X
64:n
52:]
50:4
47:H
44:B
32:]
30:4
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