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Merck
CN

20160

n-Butyllithium solution

~1.6 M in hexanes

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
PubChem Substance ID:
329751982
UNSPSC Code:
12352103
Beilstein/REAXYS Number:
1209227
MDL number:
MFCD00009414

Key Documents

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form

liquid

SMILES string

[Li]CCCC

InChI

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

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

shelf life

limited shelf life

concentration

~1.6 M in hexanes

color

yellow

density

0.68 g/mL at 25 °C

storage temp.

2-8°C

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Other Notes

This product has been replaced by 186171-ALDRICH | n-Butyllithium solution 1.6 M in hexanes

Disclaimer

a precipitate of lithium hydride can form on longer storage

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

10.4 °F - closed cup

flash_point_c

-12 °C - closed cup

Regulatory Information

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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
Bernhard J Ueberbacher et al.
Chemical communications (Cambridge, England), (28)(28), 3287-3289 (2008-07-16)
An ortho-metalation method for free ferrocenyl alcohols has been developed, which allows preparation of planar chiral ferrocene derivatives with high yields and diastereoselectivities.
Madeleine A Jacobson et al.
The Journal of organic chemistry, 67(1), 32-37 (2002-01-05)
N-(Trialkylsilyl)allylamines can be deprotonated at the cis-vinylic position to yield 3,N-dilithio-N-(trialkylsilyl)allylamines under mild conditions. N-(Trialkylsilyl)allylamines with terminal alkyl substituents were reported not to form dianions under the same conditions. During our investigations we found that N-(tert-butyldimethylsilyl)-2-buten-1-amine (1) is deprotonated under
Michael A Tarselli et al.
Organic letters, 11(20), 4596-4599 (2009-10-09)
A procedure for the coupling of aliphatic imines with allylic and allenic alkoxides is described. The success of these studies was enabled by a unique reactivity profile of Ti(IV) isopropoxide/n-BuLi compared to well-known Ti(IV) isopropoxide/RMgX systems.
Subramanian Devaraj et al.
Carbohydrate research, 344(10), 1159-1166 (2009-06-11)
O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides
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