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n-Butyllithium


Other Names:

Butyllithium

n-BuLi

BuLi





General Information:


Structure:



CAS Number: 109-72-8

Molecular Weight: 64.06 g/mol

Appearance: Colorless solution


n-BuLi is a strong base (pKa ~ 50) and is typically sold as a solution in hexanes (1.6M or 2.5M). It reacts violently with water and needs to be stored under an inert atmosphere to prevent its reacting with moisture in the air.




Common Uses:


Reagent for lithiation (typically followed by an electrophilic quench)





Reagent for lithiation-halogen exchange (typically followed by an electrophilic quench)







Strong base for forming Wittig reagents in situ





Safety:


n-Butyllithium is a strong base and is pyrophoric.




References:


1) WO2014201173, page 366

2) WO2016014463, page 93

3) WO2012129344, page 124

4) WO2015129926, page 71

5) Wikipedia: n-Butyllithium (link)

6) www.sigmaaldrich.com: n-Butyllithium solution (link)

7) Reich, H. J.; Rigby, J. H.; Handbook of Reagents for Organic Synthesis, Acidic and Basic Reagents