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Safety Information

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:
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

Signal Word

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

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

39.2 °F

Flash Point(C)

4 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBC9941V
STBC4390V
STBC4390
STBB8330
STBB6374

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Madeleine A Jacobson et al.
Journal of the American Chemical Society, 127(13), 4965-4975 (2005-03-31)
N-Lithio-N-(trialkylsilyl)allylamines can be deprotonated in the presence of ethereal solvents exclusively at the cis-vinylic position to yield 3,N-dilithio-N-(trialkylsilyl)allylamines under mild conditions. Low temperature (1)H and (7)Li NMR ((1)H NOESY, TOCSY, (1)H/(7)Li HSQC, and DO-NMR) studies on the solution structure of
J P Parente et al.
Carbohydrate research, 141(1), 41-47 (1985-08-15)
Treatment of dimethyl sulfoxide with butyllithium leads to rapid formation of lithium methylsulfinyl carbanion. The reaction products tend to be significantly freer from impurities when lithium methylsulfinyl carbanion is used rather than sodium or potassium methylsulfinyl carbanion. This reagent gives
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
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)
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
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