22560-16-3 Usage
Uses
Used in Organic Synthesis:
LITHIUM TRIETHYLBOROHYDRIDE is used as a powerful reducing agent for the conversion of carbonyl compounds to alcohols. It is particularly useful in the preparation of alkynyl alcohols from the cleavage of cyclic keto-vinyl triflates, the reduction of esters and lactones to alcohol and diol respectively, and the synthesis of 1-methylcyclohexanol and 1,4-butanediol from 1,2-epoxybutane and gamma-butyrolactone.
Used in Reagent Applications:
LITHIUM TRIETHYLBOROHYDRIDE is used as a reagent for various purposes, including:
1. Reducing alkyl halides to alkanes via dehydrogenation reactions.
2. The selective reduction of epoxides to Markovnikov alcohols.
3. Reducing tosylates or mesylates primary alcohols to hydrocarbons.
4. Reductive cyclization reactions for the preparation of useful intermediates.
5. 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.
6. Hydrodefluorination of C-F bonds using a Ni catalyst.
7. Preparation of alkynyl alcohols from the cleavage of cyclic keto-vinyl triflates.
8. Stereoselective reduction of bicyclic imides, isoquinolines, and pyridines.
9. Preparation of tungsten and molybdenum hydride complexes.
Preparation
LiBHEt3 is prepared by the reaction of lithium hydride (LiH) and triethylborane (Et3B) in tetrahydrofuran (THF):LiH + Et3B → LiEt3BHIts THF solutions are stable indefinitely in the absence of moisture and air.
Precautions
Moisture sensitive. Air sensitive. Incompatible with water and strong oxidizing agents.
References
Tamang, 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.
Check Digit Verification of cas no
The CAS Registry Mumber 22560-16-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,5,6 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 22560-16:
(7*2)+(6*2)+(5*5)+(4*6)+(3*0)+(2*1)+(1*6)=83
83 % 10 = 3
So 22560-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H16B.Li/c1-4-7(5-2)6-3;/h7H,4-6H2,1-3H3;/q-1;+1
22560-16-3Relevant articles and documents
Herbicidal oxabicyclo ethers
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, (2008/06/13)
The present invention relates to novel oxabicyclo ether derivative compounds, compositions containing these ether derivative compounds, and methods of using these compounds or compositions to control the growth of undesired vegetation. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals or broadleaf crops.
ADDITION COMPOUNDS OF ALKALI METAL HYDRIDES XVIII. REACTION OF TRIALKYLBORANES WITH t-BUTYLLITHIUM. A GENERAL CONVENIENT METHOD FOR THE PREPARATION OF LITHIUM TRIALKYBOROHYDRIDES
Brown, Herbert C.,Kramer, Gary W.,Hubbard, John L.,Krishnamurthy, S.
, p. 1 - 10 (2007/10/02)
The reaction of t-butyllithium with representative trialkylboranes possessing widely differing steric requirements was examined.This reaction occurs rapidly in ether solvents, even at -78 deg C, with formation of the corresponding lithium trialkylborohydride in quantitative yield.This synthesis is highly general, accomodating even strongly hindered trialkylboranes such as tris(trans-2-methylcyclopentyl)borane and trisiamylborane.The only by-product is isobutylene, which is generally innocuous and easily removed.The lithium trialkylborohydrides were characterized byhydride analyses, infrared spectra, and 11B NMR spectra.The formation of the trialkylborohydrides appears to be due to kinetic, rather than thermodynamic, factors.This reaction provides a highly general, facile, and quantitative route to the lithium trialkylborohydrides.