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20164

Sigma-Aldrich

n-Butyllithium solution

2.5 M in toluene, technical grade

Synonym(s):

n-BuLi, Butyl lithium, Butyllithium solution, Lithium-1-butanide

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About This Item

Linear Formula:
CH3(CH2)3Li
CAS Number:
109-72-8
Molecular Weight:
64.06
Beilstein/REAXYS Number:
1209227
MDL number:
MFCD00009414
UNSPSC Code:
12352103
PubChem Substance ID:
57647820

grade

technical grade

form

liquid

shelf life

limited shelf life

concentration

2.5 M in toluene

color

orange-red

density

0.83 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

[Li]CCCC

InChI

1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

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Caution

a precipitate of lithium hydride can form on longer storage

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

39.2 °F

flash_point_c

4 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Enantioselective total synthesis of the marine toxin (-)-gymnodimine employing a Barbier-type macrocyclization.
Ke Kong et al.
Angewandte Chemie (International ed. in English), 48(40), 7402-7405 (2009-09-04)
Deyu Li et al.
The Journal of organic chemistry, 73(6), 2373-2381 (2008-02-26)
A system consisting of a chiral lithium amide and n-BuLi in tol-d(8) solution was investigated with (1)H and (13)C INEPT DOSY, (6)Li and (15)N NMR, and other 2D NMR techniques. A mixed 2:1 trimeric complex was identified as the major
Jennifer L Rutherford et al.
Journal of the American Chemical Society, 124(2), 264-271 (2002-01-10)
6Li and (13)C NMR spectroscopic studies were carried out on [(6)Li]n-BuLi and [(6)Li]PhLi (RLi) in toluene-d(8) containing the following diamines: N,N,N',N'-tetramethylethylenediamine (TMEDA), N,N,N',N'-tetraethylethylenediamine, 1,2-dipyrrolidinoethane, 1,2-dipiperidinoethane, N,N,N',N'-tetramethylpropanediamine, trans-(R,R)-N,N,N',N'-tetramethylcyclohexanediamine, and (-)-sparteine. Dimers of general structure (RLi)(2)S(2) (S = chelating diamine) are formed
Karl J Hale et al.
Organic letters, 5(4), 503-505 (2003-02-14)
[reaction: see text] The "Southern Hemisphere" intermediate 2, used by Masamune and co-workers for their asymmetric total synthesis of bryostatin 7 (1), has been synthesized from (E)-1,4-hexadiene (11) by a 24-step pathway that has a longest linear sequence of only
Lawrence M Pratt et al.
The Journal of organic chemistry, 68(16), 6387-6391 (2003-08-05)
The effects of lithium dialkylamide structure, mixed aggregate formation, and solvation on the stereoselectivity of ketone enolization were examined. Of the lithium dialkylamides examined, lithium tetramethylpiperidide (LiTMP) in THF resulted in the best enolization selectivity. The stereoselectivity was further improved
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