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Sigma-Aldrich

n-Butyllithium solution

2.0 M in cyclohexane

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:
24858234
NACRES:
NA.22
Pricing and availability is not currently available.

form

liquid

Quality Level

200

concentration

2.0 M in cyclohexane

bp

80 °C

density

0.775 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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General description

n-Butyllithium (n-BuLi) is an organolithium reagent widely used as a strong base (superbase) in organic synthesis for the preparation of various chemical intermediates. It is also used as a reagent for lithium-halogen exchange and lithium-metal transmetalation reactions. n-BuLi is capable of lithiating carbon acids.

Application

n-Butyllithium (2.0 M in cyclohexane) can be used as:      
  • A polymerization initiator to synthesize polystyrenes by anionic polymerization of styrene.      
  • A strong base in the diastereoselective alkylation reactions.
  • A reagent to synthesize 2-benzoylpyrroles by reacting benzaldehydes with di(1H-pyrrol-1-yl)zirconium(IV) chloride complex.

Packaging

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

Legal Information

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

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 2

Flash Point(F)

-0.4 °F - closed cup

Flash Point(C)

-18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6629
SHBR6630
SHBQ6122
SHBR1404
SHBQ6121

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Lithium intercalation via n-butyllithium of the layered transition metal dichalcogenides.
Dines MB.
Materials Research Bulletin, 10(4), 287-291 (1975)
Arene-metal complexes. 13. Reaction of substituted (benzene) tricarbonylchromium complexes with n-butyllithium.
Card RJ and Trahanovsky WS.
The Journal of Organic Chemistry, 45(13), 2560-2566 (1980)
High-field proton NMR study of the aggregation and complexation of n-butyllithium in tetrahydrofuran.
McGarrity JF and Ogle CA.
Journal of the American Chemical Society, 107(7), 1805-1810 (1985)
Comparison of the synthetic utility of n-butyllithium and lithium diisopropylamide in the metalations of N, N-dialkyltoluamides.
Ludt RE, et al
The Journal of Organic Chemistry, 38(9), 1668-1674 (1973)
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
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Selective Metalation and Additions

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

Selective Metalation and Additions

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

Selective Metalation and Additions

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

Selective Metalation and Additions

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

Questions

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  1. 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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  2. 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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