Product Name

  • Name

    LITHIUM TRIETHYLBOROHYDRIDE

  • EINECS 245-076-8
  • CAS No. 22560-16-3
  • Article Data9
  • CAS DataBase
  • Density 1.45 g/cm3
  • Solubility
  • Melting Point 66-67° (Binger); mp 78-83° (dec) (Brown, 1977)
  • Formula C6H16B.Li
  • Boiling Point
  • Molecular Weight 105.945
  • Flash Point -17 °C
  • Transport Information UN 3399 4.3/PG 1
  • Appearance colorless to light grey cloudy solution
  • Safety 16-26-33-36/37/39-43-45
  • Risk Codes 11-14/15-19-34
  • Molecular Structure Molecular Structure of 22560-16-3 (LITHIUM TRIETHYLBOROHYDRIDE)
  • Hazard Symbols FlammableF; CorrosiveC
  • Synonyms Borate(1-),triethylhydro-, lithium (8CI);Borate(1-), triethylhydro-, lithium, (T-4)-(9CI);Lithium hydrotriethylborate(1-);Lithiumtriethylhydridoborate;Lithium triethylhydridoborate(1-);Lithiumtriethylhydroborate;Lithium triethylhydroborate(1-);Super-H;Superhydride;
  • PSA 0.00000
  • LogP 2.27320

Synthetic route

triethyl borane
97-94-9

triethyl borane

lithium hydride

lithium hydride

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Conditions
ConditionsYield
in an autoclave near 200°C;
in an autoclave near 200°C;
In tetrahydrofuran
triethyl borane
97-94-9

triethyl borane

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; pentane byproducts: isobutylene; (N2); to stirred soln. of boranederiv. in THF was dropwise added pentane soln. of LiBu at -78°C, then mixt. was allowed to warm up to room temp.; not isolated, detected by (11)B-NMR;>99
triethyl borane
97-94-9

triethyl borane

lithium tri-t-butoxyaluminum hydride

lithium tri-t-butoxyaluminum hydride

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Conditions
ConditionsYield
In tetrahydrofuran byproducts: Al{OC(CH3)3}; active intermediate;
In tetrahydrofuran byproducts: Al{OC(CH3)3}; active intermediate;
sodium triethylborohydride

sodium triethylborohydride

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
2: tetrahydrofuran
View Scheme
{CH3N(PF2)2}3Co2(CO)2
64799-21-9

{CH3N(PF2)2}3Co2(CO)2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

{{CH3N(PF2)2}3Co2(CO)(CHO)}(1-)

{{CH3N(PF2)2}3Co2(CO)(CHO)}(1-)

Conditions
ConditionsYield
In tetrahydrofuran reduction with excess LiEt3BH at -78°C; not isolated; various yields for various conditions.;100%
(η(6)-3-ethylanisole)tricarbonylchromium
88729-81-1

(η(6)-3-ethylanisole)tricarbonylchromium

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

(ethylbenzene)tricarbonylchromium
12203-31-5

(ethylbenzene)tricarbonylchromium

Conditions
ConditionsYield
With chlorhydric or trifluoroacetic acid In tetrahydrofuran N2-atmosphere; refluxing (2 h), acid addn.; extg. (Et2O), washing (satd. Na2CO3 soln., brine), drying (Na2SO4), filtering, evapn. (reduced pressure), recrystn. (hexane / Me2CO);100%
tris(triphenylphosphine)ruthenium(II) chloride
15529-49-4, 41756-81-4

tris(triphenylphosphine)ruthenium(II) chloride

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

hydridochlorotris(triphenylphosphine)ruthenium(II)
55102-19-7

hydridochlorotris(triphenylphosphine)ruthenium(II)

Conditions
ConditionsYield
In tetrahydrofuran IR;100%
In tetrahydrofuran; toluene (N2); stirred at room temp. for 30 min; concd.; ethanol added; cooled to -20°C; filtered; washed (ethanol and petroleum ether); dried in vacuo; NMR;>99
bis(1'-mesitylthiolatoferrocenyl)disulfane
326887-77-8

bis(1'-mesitylthiolatoferrocenyl)disulfane

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

lithium 1'-(mesitylthio)ferrocene-1-thiolate

lithium 1'-(mesitylthio)ferrocene-1-thiolate

Conditions
ConditionsYield
In tetrahydrofuran mixed, stirred for 1,5 h; not isolated;100%
(η(5):η(5)-(C5H3CO2Me)2)Mo2(CO)6
184488-45-7, 184243-69-4

(η(5):η(5)-(C5H3CO2Me)2)Mo2(CO)6

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li2(trans-1,1'-[η5:η5-(C5H3CO2Me)2]Mo2(CO)6)

Li2(trans-1,1'-[η5:η5-(C5H3CO2Me)2]Mo2(CO)6)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: Et3B; 0°C; evapn. (vac.);100%
(CH3C(CH2P(C6H5)2)3)Re(CO)2(1+)*BF4(1-)=[(CH3C(CH2P(C6H5)2)3)Re(CO)2]BF4
166989-37-3

(CH3C(CH2P(C6H5)2)3)Re(CO)2(1+)*BF4(1-)=[(CH3C(CH2P(C6H5)2)3)Re(CO)2]BF4

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

(CH3C(CH2P(C6H5)2)3)Re(CO)2(H)
166989-33-9

(CH3C(CH2P(C6H5)2)3)Re(CO)2(H)

Conditions
ConditionsYield
In tetrahydrofuran; tetrahydrofuran-d8 N2-atmosphere; detd. by NMR spectroscopy;100%
tricarbonyl[η(6)-2-chloro(trimethylsilyl)benzene]chromium

tricarbonyl[η(6)-2-chloro(trimethylsilyl)benzene]chromium

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

tricarbonyl[η(6)-4-deuterio(trimethylsilyl)benzene]chromium
138496-16-9

tricarbonyl[η(6)-4-deuterio(trimethylsilyl)benzene]chromium

Conditions
ConditionsYield
With CF3COOH In tetrahydrofuran N2-atmosphere; stirring (-78°C, 50 min), CF3COOH addn.;100%
C41H49Cl2FeNOP2

C41H49Cl2FeNOP2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C41H50ClFeNOP2

C41H50ClFeNOP2

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 28℃; Schlenk technique; Inert atmosphere; Glovebox;100%
C29H37Cl2FeNOP2

C29H37Cl2FeNOP2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C29H38ClFeNOP2

C29H38ClFeNOP2

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 28℃; Schlenk technique; Inert atmosphere; Glovebox;100%
C26H39Cl2FeNOP2

C26H39Cl2FeNOP2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C26H40ClFeNOP2

C26H40ClFeNOP2

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 28℃; Schlenk technique; Inert atmosphere; Glovebox;100%
[bis(2-diphenylphosphinophenyl)amide]PdCl

[bis(2-diphenylphosphinophenyl)amide]PdCl

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C36H29NP2Pd

C36H29NP2Pd

Conditions
ConditionsYield
In tetrahydrofuran; benzene-d6 for 0.166667h; Inert atmosphere;100%
nido-NB10H13

nido-NB10H13

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(1+)*2(CH3)2N(CH2)2N(CH3)2*{NB10H12}(1-)={Li((CH3)2N(CH2)2N(CH3)2)2}{NB10H12}

Li(1+)*2(CH3)2N(CH2)2N(CH3)2*{NB10H12}(1-)={Li((CH3)2N(CH2)2N(CH3)2)2}{NB10H12}

Conditions
ConditionsYield
In tetrahydrofuran byproducts: B(C2H5)3, H2; addn. of Li(BHEt3) in THF to soln. of the borane at -78°C, stirred for 5 min at room temp., volatiles removed in vac., addn. of THF, addn. of tmeda;; concentrated, washed three times with pentane, dried;;99%
6-azido-8,9:9,10-di-μ-hydro-1,2,3,4,5,7,7,8,9,10-decahydro-5,6-μ-amino-nido-decaborane

6-azido-8,9:9,10-di-μ-hydro-1,2,3,4,5,7,7,8,9,10-decahydro-5,6-μ-amino-nido-decaborane

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(tmeda)2(1+)-{9-azido-3,4:3,8-di-μ-hydro-undecahydro-2-aza-1,5-didebor-closo-tridecaborate(1-)}

Li(tmeda)2(1+)-{9-azido-3,4:3,8-di-μ-hydro-undecahydro-2-aza-1,5-didebor-closo-tridecaborate(1-)}

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane addn. of LiBHEt3 in THF to B-compd. in THF (0°C), stirring (15 min, room temp.), removal of volatiles (vac.), dissolution (CH2Cl2), addn. of org. compd. in CH2Cl2; reprecipitated with CH2Cl2, layered with hexane;99%
Ir(CF3)Cl(CH3CN)(CO)[P(C6H5)3]2(1+)*SbF6(1-)=[Ir(CF3)Cl(CH3CN)(CO)(P(C6H5)3)2](SbF6)
105250-39-3

Ir(CF3)Cl(CH3CN)(CO)[P(C6H5)3]2(1+)*SbF6(1-)=[Ir(CF3)Cl(CH3CN)(CO)(P(C6H5)3)2](SbF6)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Ir(CF3)HCl(CO)[P(C6H5)3]2
131100-72-6, 105250-42-8

Ir(CF3)HCl(CO)[P(C6H5)3]2

Conditions
ConditionsYield
In tetrahydrofuran addn. of 1 equiv. LiEt3BH in THF to stirred soln. of Ir-complex in THF (under N2); addn. of n-hexane, evapn. (reduced pressure), grey solid dissolved in CH2Cl2, filtered, crystn. (CH2Cl2/EtOH), elem. anal.;99%
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Si[S2Fe2(CO)6]2
71592-21-7

Si[S2Fe2(CO)6]2

Conditions
ConditionsYield
In tetrahydrofuran under N2, to the stirred soln. of 2.91 mmol Fe compd. in THF cooled to -78°C was added LiEt3BH in THF in small portions, to this was added SiCl4 over 3 min at -78°C, mixt. was warmed to room temp.; volatiles were removed in vac., solid extd. 4 times with CH2Cl2, filtered under N2 through a Celite pad supporteed on a fritted funnel, solventremoved in vac., recrystd. from CH2Cl2, elem. anal.;99%
[(CpCr(CO)2)2(μ,η(2)-P2)]

[(CpCr(CO)2)2(μ,η(2)-P2)]

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

[(CpCr(CO)2)2(μ-PH2)(μ-H)]
239134-51-1

[(CpCr(CO)2)2(μ-PH2)(μ-H)]

Conditions
ConditionsYield
In tetrahydrofuran Ar-atmosphere; excess hydride;99%
Fe2(CO)6(μ-SNMe)
88253-22-9

Fe2(CO)6(μ-SNMe)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Fe2(CO)6(μ-NHMe)(μ-SH)

Fe2(CO)6(μ-NHMe)(μ-SH)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: Et2BO2CCF3, C2H6, CF3COO(1-); Ar-atmosphere; addn. of 2 equiv. of B-compd. to Fe-complex soln. at -78°C, addn. of excess CF3COOH, warming to room temp.; solvent removal (vac.), extn. into hexane, evapn.;99%
1-(tert-butyldimethylsilyl)-2-chloro-1,2-dihydro-1,2-azaborinine
1138164-75-6

1-(tert-butyldimethylsilyl)-2-chloro-1,2-dihydro-1,2-azaborinine

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C4H4B(H)N(tert-butyldimethylsilyl)
1138164-76-7

C4H4B(H)N(tert-butyldimethylsilyl)

Conditions
ConditionsYield
In not given99%
tetrahydrofuran
109-99-9

tetrahydrofuran

C38H41ClIrOP*0.5CH2Cl2

C38H41ClIrOP*0.5CH2Cl2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C50H67IrLiO4P

C50H67IrLiO4P

Conditions
ConditionsYield
at -230℃; for 0.166667h; Inert atmosphere;99%
lithium triethylborohydride
22560-16-3

lithium triethylborohydride

17O-water
13968-48-4

17O-water

Li(17)OH

Li(17)OH

Conditions
ConditionsYield
In tetrahydrofuran byproducts: B(C2H5)3, H2; stirring stoich. amt. of H2(17)O and B-compd. in THF for 0.5 h at ca -5°C, then allowed to warm to room temp., stirred for 1 h, then under N2, solvent removed, solid heated to 100°C for 1 h, then at 250°C for 24 h at 1E-3 torr;98%
{manganese(carbonyl)5(COPh)}

{manganese(carbonyl)5(COPh)}

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(1+)*Mn(CO)4(CHO)(COC6H5)(1-)=Li[Mn(CO)4(CHO)(COC6H5)]

Li(1+)*Mn(CO)4(CHO)(COC6H5)(1-)=Li[Mn(CO)4(CHO)(COC6H5)]

Conditions
ConditionsYield
With 1,2,4,5-tetrachlorobenzene In tetrahydrofuran byproducts: (C2H5)3B; NMR tube was dried at 110°C for 30 min, rinsed with Li(C2H5)3BH and THF, flushed with N2, sealed, a soln. of Mn-complex and 1,2,4,5-tetrachlorobenzene in THF was syringed, cooled to -50°C, a soln. of Li(C2H5)3BH in THF was added; monitored by NMR (1)H;98%
(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

dichlorodimethylgermanium
1529-48-2

dichlorodimethylgermanium

((CH3)2GeS2)Fe2(CO)6
74438-41-8

((CH3)2GeS2)Fe2(CO)6

Conditions
ConditionsYield
In tetrahydrofuran under N2, to the stirred soln. of 2.91 mmol Fe compd. in THF cooled to -78°C was added LiEt3BH in THF in portions, to this was added Me2GeCl2 at -78°C, warmed to room temp.; solvent evapd., chromy. (silicic acid-CH2Cl2), recrystd. from pentane, elem. anal.;98%
Fe(η3:η2-indenide)(1,2-bis(diethylphosphino)ethane)Br

Fe(η3:η2-indenide)(1,2-bis(diethylphosphino)ethane)Br

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Fe(η3:η2-indenide)(1,2-bis(diethylphosphino)ethane)H

Fe(η3:η2-indenide)(1,2-bis(diethylphosphino)ethane)H

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 2h; Schlenk technique; Inert atmosphere;98%
Pd(Cl)N(C6H4P(CH(CH3)2)2)2
779333-78-7

Pd(Cl)N(C6H4P(CH(CH3)2)2)2

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

C24H37NP2Pd

C24H37NP2Pd

Conditions
ConditionsYield
In tetrahydrofuran at -35 - 20℃; for 1h; Inert atmosphere;98%
(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)NiCl

(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)NiCl

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)NiH

(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)NiH

Conditions
ConditionsYield
In tetrahydrofuran; benzene for 10h; Inert atmosphere;97.1%
lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li{(η5-cyclohexadienyl)tricarbonylchromium}

Li{(η5-cyclohexadienyl)tricarbonylchromium}

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere;97%
Fe(η-C5H5)(CO)2(COMe)

Fe(η-C5H5)(CO)2(COMe)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(1+)*Fe(C5H5)(CO)(CHO)(COCH3)(1-)=Li[Fe(C5H5)(CO)(CHO)(COCH3)]

Li(1+)*Fe(C5H5)(CO)(CHO)(COCH3)(1-)=Li[Fe(C5H5)(CO)(CHO)(COCH3)]

Conditions
ConditionsYield
With 1,2,4,5-tetrachlorobenzene In tetrahydrofuran byproducts: (C2H5)3B; NMR tube was dried at 110°C for 30 min, rinsed with Li(C2H5)3BH and THF, flushed with N2, sealed, a soln. of Fe-complex and 1,2,4,5-tetrachlorobenzene in THF was syringed, cooled to -50°C, a soln. of Li(C2H5)3BH in THF was added; monitored by NMR (1)H;97%
(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

ethyl iodide
75-03-6

ethyl iodide

Fe2(CO)6(μ-SEt)2

Fe2(CO)6(μ-SEt)2

Conditions
ConditionsYield
In tetrahydrofuran under N2, to the stirred soln. of 2.91 mmol Fe compd. in THF cooled to -78°C was added LiEt3BH in THF in small portions, to this was added EtI, mixt. stirred for 1 h; solvent evapd., chromy. (silicic acid-10% CH2Cl2/pentane) (a,e isomer/e,e isomer: 2.7);96%
{RuCl2(H2C(C3H3N2)2)(C8H12)}
152391-10-1

{RuCl2(H2C(C3H3N2)2)(C8H12)}

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

{RuCl(H)(H2C(C3H3N2)2)(C8H12)}
152391-12-3

{RuCl(H)(H2C(C3H3N2)2)(C8H12)}

Conditions
ConditionsYield
In tetrahydrofuran (N2; Schlenk-tube technique); a soln. of LiB(C2H5)3H in THF is added to a THF soln. of Ru complex at -78°C; stirring; allowing to warm to room temp. for 1h; pptn.;; filtration; washing with diethyl ether; elem. anal.;;96%
[Fe(η(5)-C5H5)(CO)2(C(O)-p-C6H4OMe)]

[Fe(η(5)-C5H5)(CO)2(C(O)-p-C6H4OMe)]

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

Li(1+)*Fe(C5H5)(CO)(CHO)(COC6H4OCH3)(1-)=Li[Fe(C5H5)(CO)(CHO)(COC6H4OCH3)]

Li(1+)*Fe(C5H5)(CO)(CHO)(COC6H4OCH3)(1-)=Li[Fe(C5H5)(CO)(CHO)(COC6H4OCH3)]

Conditions
ConditionsYield
With 1,2,4,5-tetrachlorobenzene In tetrahydrofuran NMR tube was dried at 110°C for 30 min, rinsed with Li(C2H5)3BH and THF, flushed with N2, sealed, a soln. of Fe-complex and 1,2,4,5-tetrachlorobenzene in THF was syringed, cooled to -50°C, a soln. of Li(C2H5)3BH in THF was added; monitored by NMR (1)H;96%

Lithium triethylborohydride Specification

The Borate(1-),triethylhydro-, lithium (1:1), (T-4)-, with the CAS registry number 22560-16-3 and EINECS registry number 245-076-8, has the systematic name of lithium triethyl(hydrido)borate(1-). It is a kind of colorless to light grey cloudy solution which is sensitive to air and moisture. And the molecular formula of the chemical is C6H16B.Li.

You should be cautious while dealing with this chemical. It is a kind of highly flammable chemical, and will reacts violently with water, and liberates extremely flammable gases. What's more, it may form explosive peroxides, and causes burns. Therefore, you had better take the following instructions: Keep away from sources of ignition - No smoking; Take precautionary measures against static discharges; In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water); In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: [Li+].CC[BH-](CC)CC
(2)InChI: InChI=1/C6H16B.Li/c1-4-7(5-2)6-3;/h7H,4-6H2,1-3H3;/q-1;+1
(3)InChIKey: WCJAYABJWDIZAJ-UHFFFAOYAV

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