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195596

Sigma-Aldrich

sec-Butyllithium solution

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

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. 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.

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
SHBN3056
STBK0878
STBJ6663
SHBL5554
SHBL4099

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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
Qinghui Wang et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 118, 32-39 (2018-03-20)
Tumor pH detection and pH value change monitoring have been of great interest in the field of nanomedicine. In this study, a pH-sensitive near-infrared fluorescence probe SiRB (Si-rhodamine and Boronic acid group) was synthesized by introducing a boronic acid group
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
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
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
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