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Sigma-Aldrich

tert-Butyllithium solution

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
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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.[1][2]

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.[2]
  • Inorganic polymer [(LiMo3Se3)n] from [(InMo3Se3)n] by reductive intercalation method.[3]
  • Adducts of cinnamic acid (1,3- and 1,4-adducts) by reacting with C-C double of cinnamic acid.[4]

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4794
SHBR3859
SHBR8812
SHBR8807
SHBR8806

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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)
t-Butyllithium
Bailey WF and Wachter-Jurcsak N
Encyclopedia of Reagents for Organic Synthesis, Second Edition (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)
On the mechanism of the addition of organolithium reagents to cinnamic acids
Aurell M, et al.
Tetrahedron, 57(6), 1067-1074 (2001)
Hsiao-Fang Wang et al.
Science advances, 6(42) (2020-10-16)
Nanonetwork-structured materials can be found in nature and synthetic materials. A double gyroid (DG) with a pair of chiral networks but opposite chirality can be formed from the self-assembly of diblock copolymers. For triblock terpolymers, an alternating gyroid (GA) with
View All Related Papers
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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