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186171

Sigma-Aldrich

n-Butyllithium solution

1.6 M in hexanes

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:
24851205
NACRES:
NA.22

form

liquid

Quality Level

200

concentration

1.6 M in hexanes

density

0.68 g/mL at 25 °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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Application

  • Copolymerization of butadiene and styrene under the influence of n-butyllithium: This study explores the copolymerization process using n-butyllithium as a catalyst, which is significant for the development of new synthetic rubber materials (V Bronskaya et al., 2023).
  • Modifiers of n-Butyllithium in the Synthesis of Polybutadiene and Styrene-Butadiene Rubbers: Explores the use of n-butyllithium with different modifiers in the synthesis of industrial rubbers, important for understanding the control of polymer properties (VS Glukhovskoi et al., 2014).
  • Aggregation and Solvation of n-Butyllithium: Examines the aggregation behavior and solvation properties of n-butyllithium in various solvents, providing insights into its chemical interactions essential for organic synthesis (O Tai et al., 2017).

Packaging

The Kilo-Lab® cylinders are only available in the US. The cylinder types will vary according to country.

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
View returnable container options.

Other Notes

May contain trace amounts of LiCl.

Legal Information

Kilo-Lab is a registered trademark of Merck KGaA, Darmstadt, Germany
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

EUH014

WGK

WGK 3

Flash Point(F)

-14.8 °F

Flash Point(C)

-26 °C

Regulatory Information

危险化学品

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How are the 100 mL, 800 mL, and 1 L unit sizes of Product 186171, Butyllithium solution, packaged?

    They are packaged in our Sure-Seal™ bottle, which have a crown cap with a PTFE/elastomer liner crimped into place.

  4. How are the 8 L and 18 L unit sizes of Product 186171, Butyllithium solution, packaged?

    They are packaged in our Kilo-Lab™ cylinder.

  5. What should I do if precipitate is present in Product 186171, Butyllithium solution?

    Haziness may form upon storage but does not affect the specification. If precipitation is present, then gently mix precipitate back into solution under an inert atmosphere.

  6. What are common uses for Product 186171, Butyllithium solution?

    Butyllithium is widely use as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS).  It is also broadly employed as a strong base (superbase) in organic synthesis, both industrially and in the laboratory.

  7. Is it necessary to handle Product 186171, Butyllithium solution, under inert atmosphere?

    This product ignites on exposure to air and should be handled under inert atmosphere such as under nitrogen.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Journal of the American Chemical Society, 111, 2981-2981 (1989)
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
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
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