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Sigma-Aldrich

tert-Butyllithium solution

1.7 M in pentane

Synonym(s):

Lithium-2-methyl-2-propanide, t-BuLi

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About This Item

Linear Formula:
(CH3)3CLi
CAS Number:
594-19-4
Molecular Weight:
64.06
Beilstein/REAXYS Number:
3587204
MDL number:
MFCD00008795
UNSPSC Code:
12352103
PubChem Substance ID:
24851206
NACRES:
NA.22

vapor density

~3 (vs air)

Quality Level

200

form

liquid

concentration

1.7 M in pentane

density

0.652 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li]C(C)(C)C

InChI

1S/C4H9.Li/c1-4(2)3;/h1-3H3;

InChI key

BKDLGMUIXWPYGD-UHFFFAOYSA-N

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General description

tert-Butyllithium solution (tert-BuLi) is an organolithium compound, used as a strong base in organic chemistry. It facilitates lithium-halogen exchange reaction and also can be employed in the deprotonation of C-H compounds and amines.

Application

tert-Butyllithium solution can be used as a strong base in the synthesis of:
  • Alkyllithium derivatives form alkyl iodides and diiodoalkanes by halogen-lithium exchange reaction.
  • Inorganic polymer [(LiMo3Se3)n] from [(InMo3Se3)n] by reductive intercalation method.
  • Adducts of cinnamic acid (1,3- and 1,4-adducts) by reacting with C-C double of cinnamic acid.

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

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Danger

Hazard Classifications

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

target_organs

Central nervous system

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 2

flash_point_f

-56.2 °F - closed cup

flash_point_c

-49 °C - closed cup

Certificates of Analysis (COA)

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Clean and convenient procedure for converting primary alkyl iodides and. alpha.,. omega.-diiodoalkanes into the corresponding alkyllithium derivatives by treatment with tert-butyllithium
Negishi E, et al.
The Journal of Organic Chemistry, 55(19), 5406-5409 (1990)
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