Skip to Content
Merck
CN

230707

n-Butyllithium solution

2.5 M in hexanes

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Linear Formula:
CH3(CH2)3Li
CAS Number:
109-72-8
Molecular Weight:
64.06
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24853832
MDL number:
MFCD00009414
Beilstein/REAXYS Number:
1209227

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

n-Butyllithium solution, 2.5 M in hexanes

InChI

1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;

SMILES string

[Li]CCCC

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

form

liquid

concentration

2.5 M in hexanes

density

0.693 g/mL at 25 °C

storage temp.

2-8°C

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

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. 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 In the polymerization of dienes, n-BuLi is employed as an initiator.
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

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.

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

signalword

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

supp_hazards

EUH014

Storage Class

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

Regulatory Information

危险化学品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBT4492
SHBT3695
SHBT2185
SDBB4109
SHBS8033

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

  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 and 800 ml unit sizes of Product 230707, 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 230707, Butyllithium solution, packaged?

    They are packaged in our Kilo-Lab™ cylinder.

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

n-Butyllithium
Ovaska TV, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
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)
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
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
View All Related Papers

Articles

Selective Metalation and Additions

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

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