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230707

Sigma-Aldrich

n-Butil-litio solution

n-Butyllithium solution

2.5 M in hexanes

Sinónimos:

n-BuLi, Butil litio, Butil-litio solution, Litio-1-butanida

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About This Item

Fórmula lineal:
CH3(CH2)3Li
Número de CAS:
109-72-8
Peso molecular:
64.06
Beilstein/REAXYS Number:
1209227
MDL number:
MFCD00009414
UNSPSC Code:
12352103
PubChem Substance ID:
24853832
NACRES:
NA.22
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form

liquid

Quality Level

200

concentration

2.5 M in hexanes

density

0.693 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li]CCCC

InChI

1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

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General description

El n-butillitio (n-BuLi) es un reactivo de organolitio comúnmente utilizado como una base fuerte en la síntesis orgánica. También se utiliza como fuente de litio para una amplia gama de bases de litio, como las amidas, las acetilidas y los alcalóxidos de litio.[1]

Application

El n-BuLi se puede utilizar como una base fuerte para formar las correspondientes sales de litio mediante desprotonación de nitrógeno, oxígeno, fósforo y ácidos de carbono. Pueden litiarse compuestos heterocíclicos, como furanos, tiofenos, oxazoles o pirroles, entre otros, α al heteroátomo del anillo usando n-BuLi. Estas sales litiadas reaccionan in situ con haluros de alquilo para obtener compuestos orgánicos útiles mediante la formación del enlace C-C.[1] El n-BuLi es también un reactivo útil para las reacciones de intercambio de litio-halógeno. La síntesis de otros varios reactivos útiles como la diisopropilamida de litio (LDA) y la difenilfosfina se realiza mediante reacción in situ con n-BuLi[2][3] En la polimerización de dienos, el n-BuLi se emplea como iniciador.[4]
El producto también se utiliza en las siguientes reacciones:      
  • Reacciones de reordenación aniónica      
  • Reacciones de intercambio de metal-halógeno y de transmetalización
  • Reacciones de eliminación      
  • Reacción de reordenación de [1,2]- y [1,4]-Wittig
  • Reacción de transposición aniónica de homo-Fries
  • Carbolitiación asimétrica

Packaging

La botella Sure/Seal™ de 25 ml se recomienda como una botella de un solo uso. Los pinchazos repetidos provocarán probablemente una disminución del rendimiento del producto.
Véase opciones de recipientes retornables.

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 - Repr. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

-7.6 °F - closed cup

flash_point_c

-22 °C - closed cup

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Certificados de análisis (COA)

Lot/Batch Number
SHBS3798
STBL4388
SHBP3836
SHBR5714
STBL4824

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n-Butyllithium
Ovaska TV, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
Microstructure-thermal property relationship of high trans-1, 4-poly (butadiene) produced by anionic polymerization of 1, 3-butadiene using an initiator composed of alkyl aluminum, n-butyl lithium, and barium alkoxide
Benvenuta-Tapia JJ, et al.
Polym. Eng. Sci., 49(1), 1-10 (2009)
Yuqiang Ma et al.
ACS nano, 9(7), 7383-7391 (2015-07-01)
Two-dimensional (2D) semiconducting monolayer transition metal dichalcogenides (TMDCs) have stimulated lots of interest because they are direct bandgap materials that have reasonably good mobility values. However, contact between most metals and semiconducting TMDCs like 2H phase WSe2 are highly resistive
Petra Rönnholm et al.
Organic letters, 9(19), 3781-3783 (2007-08-19)
A robust and scaleable route to chiral 1-isopropylamino-2-(diphenylphosphino)ethanes is described via the ring-opening of chiral, cyclic sulfamidates with potassium diphenylphosphide (KPPh(2)). The novel protocol offers a robust access to gram quantities of chiral amino phosphinoethanes in high yields. The Li-amides
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Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

Selective Metalation and Additions

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

3 Reviews This action will navigate to reviews.

Questions

1–9 of 9 Questions  

  1. 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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  2. 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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  3. Why is there a plastic layer around the glass bottle?

    1 answer

    1. The plastic (PVC) coating on the glass bottle is an added safety measure in high-wear situations. The coating also provides a degree of shatter resistance to the glass bottle, as well a an improved gripping surface when compared to non-coated glass.

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  4. What are common uses for Product 230707, Butyllithium solution?

    1 answer

    1. Butyllithium is widely use as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS).  It is also broadly employed as a strong base (superbase) in organic synthesis, both industrially and in the laboratory.

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  5. How are the 8 L and 18 L unit sizes of Product 230707, Butyllithium solution, packaged?

    1 answer

    1. They are packaged in our Kilo-Lab™ cylinder.

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  6. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  7. How are the 100 ml and 800 ml unit sizes of Product 230707, Butyllithium solution,packaged?

    1 answer

    1. They are packaged in our Sure-Seal™ bottle, which have a crown cap with a PTFE/elastomer liner crimped into place.

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  8. Is it necessary to handle Product 230707, Butyllithium solution, under inert atmosphere?

    1 answer

    1. This product ignites on exposure to air and should be handled under inert atmosphere such as under nitrogen.

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  9. What should I do if precipitate is present in Product 230707, Butyllithium solution?

    1 answer

    1. Haziness may form upon storage but does not affect the specification. If precipitation is present, then gently mix precipitate back into solution under an inert atmosphere.

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Reviews

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    • Review 1
    • Votes 0
    5 out of 5 stars.

    Dibal

    It's great . Reaction is done successfully I want to recommend this product

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  2. 2 Ratings-Only Reviews

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