Lithium Triethylborohydride

Lithium Triethylborohydride Basic information
Product Name:Lithium Triethylborohydride
Synonyms:lithiumtriethylborohydride,calselect?lt,;lithiumtriethylborohydride,calselect?lt,intetrahydrofuran;Lithium triethylborohydrideLithium triethylhydroborate;Lithium triethylborahydride (super-hydride);Super-Hydride solution,Lithium triethylborohydride solution;Lithium triethylborohydride, 1M solution in THF, AcroSeal;LithiuM triethylborohydride, 1M solution in THF, AcroSeal 100ML;LithiuM triethylborohydride, 1M solution in THF, AcroSeal 800ML
CAS:22560-16-3
MF:C6H13BLi
MW:102.92
EINECS:245-076-8
Product Categories:
Mol File:22560-16-3.mol
Lithium Triethylborohydride Structure
Lithium Triethylborohydride Chemical Properties
Melting point 66-67° (Binger); mp 78-83° (dec) (Brown, 1977)
density 0.892 g/mL at 25 °C
Fp 1 °F
storage temp. Flammables + water-Freezer (-20°C)e area
solubility Miscible with tetrahydrofuran and benzene.
form Liquid
color Colorless to light gray
Sensitive Air & Moisture Sensitive
Merck 14,5544
BRN 4151240
Exposure limitsACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
CAS DataBase Reference22560-16-3(CAS DataBase Reference)
Safety Information
Hazard Codes F,C
Risk Statements 11-14/15-19-34-40-37
Safety Statements 16-26-33-36/37/39-43-45
RIDADR UN 3399 4.3/PG 1
WGK Germany 1
10-23
HazardClass 4.3
PackingGroup I
HS Code 29319090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Lithium Triethylborohydride Usage And Synthesis
DescriptionLithium triethylborohydride is the organoboron compound with the formula LiEt3BH. Commonly referred to as LiTEBH or Superhydride, it is a powerful reducing agent used in organometallic and organic chemistry. It is a colorless or white liquid but is typically marketed and used as a THF solution. The related reducing agent sodium triethylborohydride is commercially available as toluene solutions.
LiBHEt3 is a stronger reducing agent than lithium borohydride and lithium aluminium hydride.
Chemical Propertiescolorless to light grey cloudy solution
UsesPowerful and selective reducing agent.
As a reducing agentLithium triethylborohydride is used as a powerful reducing agent in organic synthesis for the conversion of carbonyl compounds to alcohols. It is also used in the preparation of alkynyl alcohols from the cleavage of cyclic keto-vinyl triflates. It is also used in the reduction of esters and lactones to alcohol and diol respectively. Further, it is used to prepare 1-methylcyclohexanol and 1,4-butanediol from 1,2-epoxybutane and gamma-butyrolactone respectively. It is also utilized for reductive cleavage of mesylates and tosylates in synthetic organic chemistry.
UsesLiTEBH can be used as a reagent:
  • To reduce alkyl halides to alkanes via dehydrogenation reactions.
  • For the selective reduction of epoxides to Markovnikov alcohols.
  • To reduce tosylates or mesylates primary alcohols to hydrocarbons.
  • For reductive cyclization reactions for the preparation of useful intermediates.
  • In the synthesis of hepta(manno-3-deoxy-6-O-t-butyldimethylsilyl)-β-cyclodextrin by reduction of hepta(manno-2,3-anhydro-6-O-t-butyldimethylsilyl)-β-cyclodextrin.
  • For hydrodefluorination of C-F bonds using Ni catalyst.
  • To prepare alkynyl alcohols from cleavage of cyclic keto-vinyl triflates.
  • In the stereoselective reduction of bicyclic imides, isoquinolines, and pyridines.
  • To prepare tungsten and molybdenum hydride complexes.
PreparationLiBHEt3 is prepared by the reaction of lithium hydride (LiH) and triethylborane (Et3B) in tetrahydrofuran (THF):
LiH + Et3B → LiEt3BH
Its THF solutions are stable indefinitely in the absence of moisture and air.
ApplicationLithium Triethylborohydride (LiTEBH) is widely used as a powerful and selective reducing agent that shows super hydride activity in organic synthesis.
LiTEBH can be used as a reagent:
To reduce alkyl halides to alkanes via dehydrogenation reactions.
For the selective reduction of epoxides to Markovnikov alcohols.
To reduce tosylates or mesylates primary alcohols to hydrocarbons.
For reductive cyclization reactions for the preparation of useful intermediates.
In the synthesis of hepta(manno-3-deoxy-6-O-t-butyldimethylsilyl)-β-cyclodextrin by reduction of hepta(manno-2,3-anhydro-6-O-t-butyldimethylsilyl)-β-cyclodextrin.
For hydrodefluorination of C-F bonds using Ni catalyst.
To prepare alkynyl alcohols from cleavage of cyclic keto-vinyl triflates.
In the stereoselective reduction of bicyclic imides, isoquinolines, and pyridines.
To prepare tungsten and molybdenum hydride complexes.
General DescriptionSuper-Hydride? solution (Lithium triethylborohydride or LiTEBH) is widely used as a powerful and selective reducing agent that shows super hydride activity in organic synthesis.
PrecautionsMoisture sensitive. Air sensitive. Incompatible with water and strong oxidizing agents.
ReferencesTamang, S.; Kim, K.; Choi, H.; Kim, Y.; Jeong, S. Synthesis of colloidal InSb nanocrystals via in situ activation of InCl3. Dalton Trans. 2015, 44 (38), 16923-16928.
Kandapallil, B.; Colborn, R. E.; Bonitatibus, P. J.; Johnson, F. Synthesis of high magnetization Fe and FeCo nanoparticles by high temperature chemical reduction. J. Magn. Magn. Mater. 2015, 378, 535-538.
Lithium Triethylborohydride Preparation Products And Raw materials
LITHIUM TETRACHLOROCUPRATE LITHIUM ISOPROPOXIDE LITHIUM (TRIMETHYLSILYL)ACETYLIDE Methyltrimethoxysilane ETHYNYLMAGNESIUM CHLORIDE Potassium bis(trimethylsilyl)amide Triethylborane Lithium triisobutylhydroborate LITHIUM TRISIAMYLBOROHYDRIDE LITHIUM B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE LITHIUM HYDRIDO(9-BBN-NOPOL BENZYL ETHER ADDUCT) Lithium hydride Lithium Triethylborohydride LITHIUM TRIETHYLBOROHYDRIDE 1M IN THF LITHIUM TRIETHYLBOROHYDRIDE, [3H] Lithium borohydride LITHIUM B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE LITHIUM TRIETHYLBORODEUTERIDE

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