186198
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:
Molecular Weight:
64.06
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3587204
Concentration:
1.7 M in pentane
Form:
liquid
vapor density
~3 (vs air)
Quality Level
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
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.
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
WGK 2
flash_point_f
-56.2 °F - closed cup
flash_point_c
-49 °C - closed cup
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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)
On the mechanism of the addition of organolithium reagents to cinnamic acids
Aurell M, et al.
Tetrahedron, 57(6), 1067-1074 (2001)
Room-temperature synthesis of (LiMo3Se3) n and the determination of the relative reduction potential of tert-butyllithium
Golden JH, et al.
Chemistry of Materials, 6(6), 844-849 (1994)