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186198

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:
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

Signal Word

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 Code

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Alkyl lithium
Hazardous rank II

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

186198-20L:
186198-4X100ML:
186198-18L:
186198-18L-C:
186198-100ML:4548173929699
186198-4X25ML:
186198-VAR:
186198-1L:
186198-50ML:
186198-4X10ML:
186198-800ML:4548173355061
186198-BULK:
186198-8L:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8124
SHBP2807
STBK5818
STBK5355
SHBM1910

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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)
Adeline Huiling Loo et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 16(11), 2304-2306 (2015-05-28)
Owing to the attractive properties that transition metal dichalcogenides (TMDs) display, they have found recent application in the fabrication of biosensing devices. These devices involve the immobilization of a recognition element such as DNA onto the surface of TMDs. Therefore
Xinyi Chia et al.
ACS nano, 9(5), 5164-5179 (2015-04-22)
Layered transition metal dichalcogenides (TMDs) have been the center of attention in the scientific community due to their properties that can be tapped on for applications in electrochemistry and hydrogen evolution reaction (HER) catalysis. We report on the effect of
Shigeo Hayashi et al.
Journal of enzyme inhibition and medicinal chemistry, 29(6), 846-867 (2014-02-13)
Because of the pivotal role of cyclooxygenase (COX) in the inflammatory processes, non-steroidal anti-inflammatory drugs (NSAIDs) that suppress COX activities have been used clinically for the treatment of inflammatory diseases/syndromes; however, traditional NSAIDs exhibit serious side-effects such as gastrointestinal damage

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