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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
concentration:
1.6 M in hexanes
To inquire about this product 186171, please contact your local Merck office or dealer. Contact Technical Service

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

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-14.8 °F - closed cup

Flash Point(C)

-26 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3903
SHBS3443
SHBP4377
STBL3586
STBL4233

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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
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
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
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Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

Questions

1–8 of 8 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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

    1 answer

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

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

    1 answer

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

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

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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

    1 answer

    1. They are packaged in our Kilo-Lab™ cylinder.

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

    1 answer

    1. 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.

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