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230707

Sigma-Aldrich

正丁基锂 溶液

n-Butyllithium solution

2.5 M in hexanes

别名:

1-丁基锂, n-BuLi, Butyl lithium, 丁基锂 溶液

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About This Item

线性分子式:
CH3(CH2)3Li
CAS号:
109-72-8
分子量:
64.06
Beilstein:
1209227
MDL號碼:
MFCD00009414
分類程式碼代碼:
12352103
PubChem物質ID:
24853832
NACRES:
NA.22
濃度:
2.5 M in hexanes
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形狀

liquid

品質等級

200

濃度

2.5 M in hexanes

密度

0.693 g/mL at 25 °C

儲存溫度

2-8°C

SMILES 字串

[Li]CCCC

InChI

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

InChI 密鑰

MZRVEZGGRBJDDB-UHFFFAOYSA-N

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一般說明

正-丁基锂溶液(n-BuLi)是一种有机锂化合物，通常用作有机化学中的强碱。它还被用作各种锂基的锂源，例如氨基化锂、乙炔化锂和烷氧基锂。[1]

應用

n-BuLi可作为强碱通过氮、氧、磷和碳酸的去质子化反应形成相应的锂盐。杂环化合物，如呋喃、噻吩、噁唑、吡咯等，可以使用 n-BuLi锂化 α 到环杂原子上。这些锂化盐与卤代烷原位反应，通过形成C-C键获得有用的有机化合物。[1] n-BuLi也是用于锂-卤素交换反应的有效试剂。通过使用 n-BuLi的原位反应还可合成许多其他有用试剂，如二异丙基氨基锂（LDA）和二苯基膦[2][3] 。在双烯聚合反应中， n-BuLi用作引发剂。[4]
产物也被用于以下反应：      
  • 阴离子重排反应      
  • 金属-卤素互换和转移金属化反应
  • 消除反应      
  • [1,2]- 和 [1,4]-维蒂希重排反应      
  • 阴离子homo-Fries重排反应      
  • 不对成碳锂化反应

包裝

25mL Sure/Seal™瓶推荐用作一次性瓶。 反复穿刺可能导致产品性能下降。
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法律資訊

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

訊號詞

Danger

危險分類

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

標靶器官

Central nervous system

安全危害

EUH014

儲存類別代碼

4.2 - Pyrophoric and self-heating hazardous materials

水污染物質分類（WGK）

WGK 3

閃點（°F）

-7.6 °F - closed cup

閃點（°C）

-22 °C - closed cup

历史批次信息供参考:

分析证书(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)
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)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
Jennifer L Rutherford et al.
Journal of the American Chemical Society, 124(2), 264-271 (2002-01-10)
6Li and (13)C NMR spectroscopic studies were carried out on [(6)Li]n-BuLi and [(6)Li]PhLi (RLi) in toluene-d(8) containing the following diamines: N,N,N',N'-tetramethylethylenediamine (TMEDA), N,N,N',N'-tetraethylethylenediamine, 1,2-dipyrrolidinoethane, 1,2-dipiperidinoethane, N,N,N',N'-tetramethylpropanediamine, trans-(R,R)-N,N,N',N'-tetramethylcyclohexanediamine, and (-)-sparteine. Dimers of general structure (RLi)(2)S(2) (S = chelating diamine) are formed
Deyu Li et al.
The Journal of organic chemistry, 73(6), 2373-2381 (2008-02-26)
A system consisting of a chiral lithium amide and n-BuLi in tol-d(8) solution was investigated with (1)H and (13)C INEPT DOSY, (6)Li and (15)N NMR, and other 2D NMR techniques. A mixed 2:1 trimeric complex was identified as the major
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Selective Metalation and Additions

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

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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. 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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  5. 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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  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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