Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

230707

Sigma-Aldrich

n-Butyllithium solution

n-Butyllithium solution

2.5 M in hexanes

Synonym(s):

n-BuLi, Butyl lithium, Butyllithium solution, Lithium-1-butanide

Sign Into View Organizational & Contract Pricing
All Photos(3)

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:
24853832
NACRES:
NA.22
Pricing and availability is not currently available.

form

liquid

Quality Level

200

concentration

2.5 M in hexanes

density

0.693 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

Looking for similar products? Visit Product Comparison Guide

General description

n-Butyllithium (n-BuLi) is an organolithium reagent commonly used as a strong base in organic synthesis. It is also used as a lithium source for a wide range of lithium bases, such as lithium amides, acetylides, and alkoxides.[1]

Application

n-BuLi can be used as a strong base to form corresponding lithium salts by the deprotonation of nitrogen, oxygen, phosphorus, and carbon acids. Heterocyclic compounds, such as furans, thiophenes, oxazoles, pyrroles, etc, can be lithiated α to the ring heteroatom using n-BuLi. These lithiated salts react in situ with alkyl halides to obtain useful organic compounds by the formation of the C-C bond.[1] n-BuLi is also a useful reagent for lithium–halogen exchange reactions. Synthesis of various other useful reagents such as lithium diisopropylamide (LDA) and diphenylphosphine is done by in situ reaction with n-BuLi[2][3] In the polymerization of dienes, n-BuLi is employed as an initiator.[4]
The product is also used in the following reactions:      
  • Anionic rearrangement reactions      
  • Metal-halogen interchange and transmetalation reactions
  • Elimination reactions      
  • [1,2]- and [1,4]-Wittig rearrangement reaction      
  • Anionic homo-Fries rearrangement reaction      
  • Asymmetric carbolithiation

Packaging

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.

Legal Information

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)

-7.6 °F - closed cup

Flash Point(C)

-22 °C - closed cup

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBS3798
STBL4388
SHBP3836
SHBR5714
STBL4824

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

n-Butyllithium
Ovaska TV, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Microstructure-thermal property relationship of high trans-1, 4-poly (butadiene) produced by anionic polymerization of 1, 3-butadiene using an initiator composed of alkyl aluminum, n-butyl lithium, and barium alkoxide
Benvenuta-Tapia JJ, et al.
Polym. Eng. Sci., 49(1), 1-10 (2009)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
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
View All Related Papers

Articles

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.

3 Reviews This action will navigate to reviews.

Questions

1–9 of 9 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

      Helpful?

  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

      Helpful?

  3. Why is there a plastic layer around the glass bottle?

    1 answer

    1. The plastic (PVC) coating on the glass bottle is an added safety measure in high-wear situations. The coating also provides a degree of shatter resistance to the glass bottle, as well a an improved gripping surface when compared to non-coated glass.

      Helpful?

  4. How are the 8 L and 18 L unit sizes of Product 230707, Butyllithium solution, packaged?

    1 answer

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

      Helpful?

  5. What are common uses for Product 230707, 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.

      Helpful?

  6. 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.

      Helpful?

  7. How are the 100 ml and 800 ml unit sizes of Product 230707, 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.

      Helpful?

  8. What should I do if precipitate is present in Product 230707, 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.

      Helpful?

  9. Is it necessary to handle Product 230707, 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.

      Helpful?

Reviews

Active Filters

    • Review 1
    • Votes 0
    5 out of 5 stars.

    Dibal

    It's great . Reaction is done successfully I want to recommend this product

    Helpful?

  2. 2 Ratings-Only Reviews

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service