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151076

Sigma-Aldrich

9-硼双环[3.3.1]壬烷 溶液

0.5 M in THF

同義詞:

9-BBN

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About This Item

經驗公式(希爾表示法):
C8H15B
CAS號碼:
分子量::
122.02
Beilstein:
605509
MDL號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22
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形狀

liquid

品質等級

反應適用性

reagent type: reductant

濃度

0.5 M in THF

密度

0.894 g/mL at 25 °C

SMILES 字串

B1C2CCCC1CCC2

InChI

1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2/t7-,8+

InChI 密鑰

FEJUGLKDZJDVFY-OCAPTIKFSA-N

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一般說明

9-Borabicyclo[3.3.1]壬烷是一种有机化合物,通常可用作氢硼酸酯化剂。与其他二烷基硼烷相比,它具有热稳定性,对氧气和水不敏感。它通常可用于利用炔烃制备醛。[1][2]

應用

使用 9-BBN 对相应环状缩醛进行还原以鉴别对称二醇。[3]
烯烃保护基团†

反应物用于:
  • 线性SPPS合成泛素衍生物
  • 铜催化有机硼化合物与伯烷基卤化物和拟卤化物发生交叉偶联反应
  • 将烯烃分子内插入钯-氮键
  • 制备(膦酰基乙酰基)鸟氨酸以研究对酵母中精氨酸生物合成基因的影响
  • Hetero-Diels-Alder反应合成螺环生物碱
选择性硼氢化还原试剂。[4][5][6]

包裝

建议将25 mL Sure/Seal瓶作为一次性瓶使用。 反复扎刺可能会使产品性能下降。

法律資訊

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

訊號詞

Danger

危險分類

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 1

標靶器官

Central nervous system, Respiratory system

安全危害

儲存類別代碼

4.3 - Hazardous materials which set free flammable gases upon contact with water

水污染物質分類(WGK)

WGK 3

閃點(°F)

1.0 °F - closed cup

閃點(°C)

-17.2 °C - closed cup


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分析證明 (COA)

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Preparation and properties
Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) (2007)
Zhishan Bo et al.
Organic letters, 6(5), 667-669 (2004-02-28)
Several useful aryl/alkyl building blocks for dendrimer and hyperbranched polymer synthesis were prepared by Suzuki-Miyaura cross-coupling reactions and iododesilylation reactions. The iododesilylations were carried out with iodine monochloride (ICl) in methylene chloride and diethyl ether (10:1). This solvent combination lowered
Chemistry Letters (Jpn), 33, 396-397 (2004)
Chemtracts, 13, 219-222 (2000)
Organic Process Research & Development, 10, 1076-1076 (2006)

文章

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf

Questions

1–3 of 3 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

      Helpful?

  3. Can you please share the method on how you determine the hydrogen evolution to check the molarity of 9-BBN in THF.

    1 answer
    1. This product is only MQ100 quality level, which means details on the QC methods cannot be shared. For more information on our M-Clarity program, please see: https://www.sigmaaldrich.com//life-science/quality-and-regulatory-management/m-clarity-program

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