594-19-4 Usage
Chemical Description
Different sources of media describe the Chemical Description of 594-19-4 differently. You can refer to the following data:
1. Tert-butyllithium is an organolithium reagent commonly used in organic synthesis.
2. tert-Butyllithium is used as a solution in pentane and is titrated before use.
3. tert-butyllithium is an organolithium compound that is commonly used in organic synthesis.
Description
tert-Butyllithium solution (tert-BuLi) is an organolithium compound, used as a strong base in organic chemistry. It facilitates lithium-halogen exchange reaction and also can be employed in the deprotonation of C-H compounds and amines. it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. Its synthesis was first reported by R. B. Woodward in 1941.
Chemical Properties
tert-Butyllithium is a colorless crystalline solid or colourless to pale yellow solution. It is more reactive than n- or sec-butyllithium and has similar properties. However, it is thermally stable. Dixon and co-workers have heated tert-Butyllithium to 100°C for 20 hr with little decomposition.
Uses
There are no commercial uses of t-butyllithium, but it is used as a polymerization initiator and as a metalating agent in the laboratory.
Alkylating and metalating agent. Reagent for the introduction of the tert-butyl group.
tert-Butyllithium (t-BuLi) is the most reactive of the commercially available organolithium reagents. It is supplied as a standard solution in hydrocarbon solvents, usually in a bottle sealed with a septum.
Preparation
tert-Butyllithium is not sold in large quantities. The
industrial and laboratory preparations are the same: the reaction of t-butyl chloride with
lithium metal in a hydrocarbon solvent. However, tert-Butyllithium is much more difficult to
produce than the other isomeric butyllithium compounds and some special precautions
must be taken to obtain good yields. Principally, the lithium metal must be finely divided
and must contain several percent sodium. It has also been found that t-butyl alcohol in
the butyl chloride is beneficial. The solvent of choice is pentane. Vigorous reflux is necessary for good yield since it apparently helps to remove lithium chloride from the
surface of the metal, and pentane refluxes at about the optimum temperature. If hexane is
used at the same temperature, a significantly lower yield is obtained.
Application
tert-Butyllithium solution can be used as a strong base in the synthesis of:Alkyllithium derivatives form alkyl iodides and diiodoalkanes by halogen-lithium exchange reaction.Inorganic polymer [(LiMo3Se3)n] from [(InMo3Se3)n] by reductive intercalation method.Adducts of cinnamic acid (1,3- and 1,4-adducts) by reacting with C-C double of cinnamic acid.
Check Digit Verification of cas no
The CAS Registry Mumber 594-19-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 4 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 594-19:
(5*5)+(4*9)+(3*4)+(2*1)+(1*9)=84
84 % 10 = 4
So 594-19-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H9.Li/c1-4(2)3;/h1-3H3;/rC4H9Li/c1-4(2,3)5/h1-3H3
594-19-4Relevant articles and documents
Kamienski,Esmay
, p. 1807 (1960)
METHOD FOR PRODUCING ALKYL LITHIUM COMPOUNDS AND ARYL LITHIUM COMPOUNDS BY MONITORING THE REACTION BY MEANS OF IR-SPECTROSCOPY
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Page/Page column 10-11, (2008/06/13)
The invention relates to a method for producing alkyl lithium compounds and aryl lithium compounds by reacting lithium metal with alkyl or aryl halogenides in a solvent, the concentration of the alkyl/aryl halogenide and the alkyl/aryl lithium compound being detected according to an in-line measurement in the reactor by means of IR spectroscopy, and an exact recognition of the end point of the dosing of the halogenide constituents being carried out by evaluation of the IR measurement. Said method enables an optimum reactive process and reaction yield. The identification of the respective concentration of the educt and the product is a reliable reactive process. The yield of the reaction is also optimised by determining the end point of the halogenide dosing, as is the purity of the product due to a lower concentration thereof during the reaction.
Fluorous phosphines and process for their preparation
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, (2008/06/13)
A fluorous phosphine wherein the phosphor is coupled to at least one aryl or alkyl moiety, to which moiety a fluorous tail is coupled, wherein a spacer group, containing a non-carbon atom, is positioned between the aryl or alkyl moiety and the fluorous tail, a process for the preparation of said phosphines, metalcomplexes, catalysts and catalyst compounds therefrom and their use in catalysis.
ASYMMETRIC OXIDATION OF SULFIDES MEDIATED BY CHIRAL TITANIUM COMPLEXES: MECHANISTIC AND SYNTHETIC ASPECTS
Zhao, S. H.,Samuel, O.,Kagan, H. B.
, p. 5135 - 5144 (2007/10/02)
Asymmetric oxidation of sulfides by hydroperoxides mediated by chiral titanium complexes was further developed.The effect of water was discussed as well as steric and electronic factors of aryl groups in aryl-S-alkyl oxidation.When aryl is replaced by 1-alkyne, the sulfoxude is still obtained with hihg ee.The enantioselectivity of oxidation is enhanced by using cumene hydroperoxide instead of t-butyl hydroperoxide (up to 96percent).The asymmetric oxidation was also run under catalytic conditions (with respect to the titanium complex) and beneficial effects were observed in the presence of molecular sieves in the reaction medium.
