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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:
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yuqiang Ma et al.
ACS nano, 9(7), 7383-7391 (2015-07-01)
Two-dimensional (2D) semiconducting monolayer transition metal dichalcogenides (TMDCs) have stimulated lots of interest because they are direct bandgap materials that have reasonably good mobility values. However, contact between most metals and semiconducting TMDCs like 2H phase WSe2 are highly resistive
Petra Rönnholm et al.
Organic letters, 9(19), 3781-3783 (2007-08-19)
A robust and scaleable route to chiral 1-isopropylamino-2-(diphenylphosphino)ethanes is described via the ring-opening of chiral, cyclic sulfamidates with potassium diphenylphosphide (KPPh(2)). The novel protocol offers a robust access to gram quantities of chiral amino phosphinoethanes in high yields. The Li-amides
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
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)
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