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Sigma-Aldrich

sec-Butyllithium solution

sec-Butyllithium solution
1 of 3 reviewers received a sample product or took part in a promotion

1.4 M in cyclohexane

Synonym(s):

Lithium-2-butanide, s-BuLi

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About This Item

Linear Formula:
CH3CH2CH(CH3)Li
CAS Number:
598-30-1
Molecular Weight:
64.06
Beilstein:
3587206
MDL number:
MFCD00009323
UNSPSC Code:
12352103
PubChem Substance ID:
24851700
NACRES:
NA.22
Pricing and availability is not currently available.

form

liquid

Quality Level

200

concentration

1.4 M in cyclohexane

density

0.769 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li]C(C)CC

InChI

1S/C4H9.Li/c1-3-4-2;/h3H,4H2,1-2H3;

InChI key

VATDYQWILMGLEW-UHFFFAOYSA-N

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Application

sec-Butyllithium solution (1.4M in cyclohexane) has been used in the multi-step synthesis of 5-methyl-5,6-dihydrothymidine (5-MDHT) from thymidine.[1] It has also been used in the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers in the presence of a chiral ligand.[2]

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

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - 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)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS3401
SHBQ9596
STBL2742
SHBQ5914
STBL0210

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Cheng Chen et al.
Organic & biomolecular chemistry, 15(25), 5364-5372 (2017-06-16)
A series of 6,6-dihalo-2-azabicyclo[3.1.0]hexane and 7,7-dihalo-2-azabicyclo[4.1.0]heptane compounds were prepared by the reaction of dihalocarbene species with N-Boc-2,3-dihydro-1H-pyrroles or -1,2,3,4-tetrahydropyridines. Monochloro substrates were synthesised as well, using a chlorine-to-lithium exchange reaction. The behaviour of several aldehydes and ketones under reductive amination
Lukasz Otulakowski et al.
Polymers, 12(1) (2020-01-17)
In this work, the self-assembly of a series of amphiphilic polystyrene-b-polyglycidol (PS-b-PGL) diblock copolymers in dioxane and dioxane/water mixtures is presented. The PS-b-PGL have an average degree of polymerization (DP) of PS block equal to 29 units and varied degrees
Jason V Chari et al.
The Journal of organic chemistry, 84(6), 3652-3655 (2019-03-07)
Silyl triflate precursors to cyclic alkynes and allenes serve as valuable synthetic building blocks. We report a concise and scalable synthetic approach to prepare the silyl triflate precursors to cyclohexyne and 1,2-cyclohexadiene. The strategy involves a retro-Brook rearrangement of an
Dimitrios Moschovas et al.
Nanomaterials (Basel, Switzerland), 10(8) (2020-08-06)
The synthesis, molecular and morphological characterization of a 3-miktoarm star terpolymer of polystyrene (PS, M¯n = 61.0 kg/mol), polybutadiene (PB, M¯n = 38.2 kg/mol) and polyisoprene (PI, M¯n = 29.2 kg/mol), corresponding to volume fractions (φ) of 0.46, 0.31 and
Leixing Chen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(68), 18012-18019 (2018-11-15)
Although living polymerization methods are widely applicable to organic monomers, their application to inorganic monomers is rare. For the first time, we show that the living poly(methylenephosphine) (PMPn- ) anion can function as a macroinitiator for olefins. Specifically, the phosphaalkene
View All Related Papers
3 Reviews This action will navigate to reviews.

Questions

Reviews

1 of 3 reviewers received a sample product or took part in a promotion
1–2 of 3 Reviews  

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  1. South West, UK
    • Review 1
    • Votes 6
    2 out of 5 stars.

    Titrate your s-BuLi before use

    s-BuLi when titrated came to about 0.73 M not the 1.4 M stated on the bottle

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for taking the time to leave a review! sec-Butyllithium is very sensitive to air, moisture and temperature and should be handled under inert atmosphere. During storage a white precipitate of lithium hydride may form as it slowly decomposes, which is part of the characteristics of this chemical resulting in a limited shelf life. We would love to learn more about your experience and see if there is anything more we can do to help with this issue. When you have a moment, please contact us by visiting https://www.sigmaaldrich.com/support/customer-support and submit a Product Technical Inquiry. We look forward to hearing from you soon!

  2. South West
    • Review 1
    • Votes 6
    1 out of 5 stars.

    Highly turbid, with sediment that doesn't settle

    Highly turbid, with sediment that doesn't settle, giving inconsistent results. Titre is less than half than marketed.

    Helpful?

    1. Response from MilliporeSigma:

      Thank you for taking the time to leave a review! We are sorry to hear that your experience did not meet expectations. We would like to learn more about your experience to see if there is anything we can do to help troubleshoot this issue. When you have a moment, please contact us by visiting https://www.sigmaaldrich.com/support/customer-support and submit a Report Product Issue ticket. We look forward to hearing from you soon!

  3. 1 Ratings-Only Review

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