186171

Sigma-Aldrich

n-Butyllithium solution

1.6 M in hexanes

Synonym(s):
Butyl lithium, Lithium-1-butanide, Butyllithium solution, n-BuLi
Linear Formula:
CH3(CH2)3Li
CAS Number:
Molecular Weight:
64.06
Beilstein/REAXYS Number:
1209227
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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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Packaging

1 L in Sure/Seal™
8, 18 L in Kilo-Lab™
4×25, 50, 100, 4×100, 800 mL in Sure/Seal™
The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Other Notes

May contain trace amounts of LiCl.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

signalword

Danger

hazcat

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

Supp Hazards

EUH014

storage_class_code

4.2 - Pyrophoric and self-heating hazardous materials

WGK Germany

WGK 3

Flash Point F

-14.8 °F - closed cup

Flash Point C

-26 °C - closed cup

Certificate of Analysis

Certificate of Origin

  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)
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...
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...
Graeme Barker et al.
Organic letters, 12(18), 4176-4179 (2010-08-20)
A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered...
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...

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