sec-Butyllithium

sec-Butyllithium

Skeletal formula of sec-butyllithium
Names
IUPAC name sec-Butyllithium
Systematic IUPAC name Butan-2-yllithium
Identifiers
CAS Number	598-30-1 Y
Beilstein Reference	3587206
ChemSpider	10254345 Y
EC Number	209-927-7
Jmol 3D model	Interactive image Interactive image
PubChem	102446
InChI InChI=1S/C4H9.Li/c1-3-4-2;/h3H,4H2,1-2H3; Y Key: VATDYQWILMGLEW-UHFFFAOYSA-N Y InChI=1/C4H9.Li/c1-3-4-2;/h3H,4H2,1-2H3;/rC4H9Li/c1-3-4(2)5/h4H,3H2,1-2H3 Key: VATDYQWILMGLEW-MHILWDCKAX
SMILES [Li]C(C)CC CC([Li])CC
Properties
Chemical formula	C4H9Li
Molar mass	64.06 g·mol−1
Acidity (pKa)	51
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

sec-Butyllithium is an organometallic compound with the formula CH₃CHLiCH₂CH₃, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.

sec-BuLi can be prepared by the reaction of sec-butyl halides with lithium metal:

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The carbon-lithium bond is highly polar, rendering the carbon basic, as in other organolithium reagents. Sec-butyllithium is more basic than the primary organolithium reagent, n-butyllithium. It is also more sterically hindered, though it is still useful for syntheses.

sec-BuLi is employed for deprotonations of particularly weak carbon acids where the more conventional reagent n-BuLi is unsatisfactory. It is, however, so basic that its use requires greater care than for n-BuLi. For example diethyl ether is attacked by sec-BuLi at room temperature in minutes, whereas ether solutions of n-BuLi are stable. Many transformations involving sec-butyllithium are similar to those involving other organolithium reagents. For example, sec-BuLi react with carbonyl compounds and esters to form alcohols. With copper(I) iodide sec-BuLi forms lithium di-sec-butylcuprates. The first two reactions can also be accomplished by using sec-butylmagnesium bromide, a Grignard reagent; in fact, the latter is the typical reagent for this purpose.