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Merck
CN

939412

n-Butyllithium solution

2.5 M (in PAO/hexanes mixture)

Synonym(s):

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

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About This Item

Linear Formula:
CH3(CH2)3Li
CAS Number:
Molecular Weight:
64.06
UNSPSC Code:
12352142
Beilstein/REAXYS Number:
1209227
MDL number:
NACRES:
NA.22
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Product Name

n-Butyllithium solution, 2.5 M (in PAO/hexanes mixture)

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

SMILES string

[Li]CCCC

InChI

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

form

liquid

concentration

2.5 M (in PAO/hexanes mixture)

color

colorless to yellow

storage temp.

2-8°C

Quality Level

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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

Features and Benefits

This n-BuLi formulation in PAO/hexanes is:
  • Considered non-pyrophoric demonstrated using EPA’s SW-846 Test Method 1050
  • Maintains the same reactivity as traditional n-BuLi reagents
  • Compatible with traditional lithiation additives like KOtBu or TMEDA
  • More bench stable than traditional n-BuLi reagents

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. This n-BuLi is a solution in poly-α-olefin (PAO)/hexanes solvent mixture is considered non-pyrophoric which is demonstrated using EPA’s SW-846 Test Method 1050.

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Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 3 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 Inhalation - Water-react 1

target_organs

Nervous system

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 3

flash_point_f

88.7 °F

flash_point_c

31.5 °C

Regulatory Information

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Articles

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

Non-pyrophoric t-BuLi and n-BuLi formulations offer robust reactivity with improved handling.

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