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Merck

347116

Sigma-Aldrich

碘化钐(II) 溶液

0.1 M in THF, contains samarium chips as stabilizer

别名:

碘化亚钐

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25 ML
$113.00
4 X 25 ML
$170.00
100 ML
$181.00
1 L
$573.00

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25 ML
$113.00
4 X 25 ML
$170.00
100 ML
$181.00
1 L
$573.00

About This Item

线性分子式:
SmI2
CAS号:
分子量:
404.17
MDL编号:
UNSPSC代码:
12352302
PubChem化学物质编号:
NACRES:
NA.22

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表单

liquid

质量水平

包含

samarium chips as stabilizer

反应适用性

core: samarium
reagent type: catalyst
reaction type: Reductions

reagent type: reductant

浓度

0.1 M in THF

密度

0.922 g/mL at 25 °C

储存温度

2-8°C

SMILES字符串

I[Sm]I

InChI

1S/2HI.Sm/h2*1H;/q;;+2/p-2

InChI key

UAWABSHMGXMCRK-UHFFFAOYSA-L

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应用

碘化钐(II)(SmI2)作为一种试剂,用于合成:
  • 通过SmI2诱导的吲哚衍生物的环化生成的苯环吡咯里西啶和吲哚里西啶。[1]
  • 通过不对称Reformatsky型反应合成手性4-取代2-恶唑烷酮和5,5-二取代恶唑烷酮。[2]
  • γ通过羰游基-烯烃偶联反应生成-氨烷基取代γ-丁内酯。[3]

还可用于:
  • 使用SmI2/H2O/胺混合物还原共轭双键和三键成烯烃。[4]
  • 通过SmI2/H2O/Et3N将β-羟基酮转化成1,3-二醇。[5]
  • 使用SmI2/H2O试剂系统选择性还原六元内酯成相应的二醇/三醇。[6]

SmI2是一种有效的单电子还原剂,用于在温和条件下促进酮烯烃、羰游基芳香基环化和频哪醇偶联反应。[7][8][9]通常,分子内[10]和分子间偶联[10]都以较高的立体选择性方式进行。此外,它还用于合成新型芳氧钐/环戊二烯配合物。[11][12]

包装

建议将25 mL Sure/Seal 瓶作为一次性瓶使用。 反复穿刺可能会导致产品性能下降。

法律信息

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

警示用语:

Danger

危险分类

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 3

靶器官

Central nervous system, Respiratory system

补充剂危害

储存分类代码

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

WGK

WGK 3

闪点(°F)

-2.2 °F - closed cup - Solvent

闪点(°C)

-19 °C - closed cup - Solvent

个人防护装备

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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One-Step Highly Diastereoselective Synthesis of γ-Aminoalkyl-Substituted γ-Butyrolactones by an Asymmetric Samarium-Mediated Ketyl-Alkene Coupling Reaction
Fukuzawa S-I, et al.
The Journal of Organic Chemistry, 68(5), 2042-2044 (2003)
Reduction of β-Hydroxyketones by SmI2/H2O/Et3N
Davis TA, et al.
Organic Letters, 7(1), 119-122 (2005)
Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups
Motoi Kawatsura FM and Haruhisa Shirahama
The Journal of Organic Chemistry, 59, 6900-6900 (1994)
Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI2 and H2O
Parmar D, et al.
Journal of the American Chemical Society, 131(42), 15467-15473 (2009)
Selective reduction of carbon-carbon double and triple bonds in conjugated olefins mediated by SmI2/H2O/amine in THF
Dahlen A and Hilmersson G
Tetrahedron Letters, 44(13), 2661-2664 (2003)

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Rare earth elements are vital in everyday life worldwide: catalysts in cars, colors in screens, magnets in electronics. Essential for modern living.

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    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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    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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