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418218

Sigma-Aldrich

三氟甲磺酸钪 (III)

99%

别名:

Sc(OTf)3, 三氟甲基磺酸钪, 三氟甲磺酸 钪(III) 盐

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About This Item

线性分子式:
Sc(SO3CF3)3
CAS号:
144026-79-9
分子量:
492.16
Beilstein:
8510151
MDL编号:
MFCD00192433
UNSPSC代码:
12161600
PubChem化学物质编号:
24866212
NACRES:
NA.22
价格与库存信息目前不能提供

质量水平

100

方案

99%

表单

powder

反应适用性

core: scandium
reagent type: catalyst

SMILES字符串

[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChI key

HZXJVDYQRYYYOR-UHFFFAOYSA-K

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相关类别

一般描述

三氟甲磺酸钪是一种非常活跃、高效、可回收和可重复使用的酰化催化剂。[1]三氟甲磺酸钪是弗里德尔-克拉夫茨酰化反应、狄尔斯-阿尔德反应和其他碳-碳键形成反应的重要催化剂。[2] 它还可以立体化学催化丙烯酸酯的自由基聚合反应。[3](4′S,5′S)-2,6-双[4′-(三异丙基)氧甲基-5′-苯基-1′,3′-恶唑啉-2′-yl]吡啶的三氟甲磺酸钪络合物，已被用作取代吲哚与甲基(E)-2-氧代-4-芳基-3-丁烯酸甲酯之间的不对称弗里德尔-克拉夫茨反应的催化剂。[4]

应用

三氟甲磺酸钪作为催化剂用于：
  • 芳香族和脂肪族硫醇的加氢硫醇反应。[5]
  • 二茂铁衍生物对O2的选择性双电子还原。[6]
  • 吲哚和吡咯在水中的烷基化反应。[7]
  • β腈酮的合成。[8]
  • 与三乙基硅烷结合，通过还原方式开放功能化的吡喃糖苷环。[9]
  • 通过稳定的硫叶立德合成牛酮的关键步骤。[10]

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000396474
0000396474
0000430672
0000430672
MKCW7694

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1 of 2

三氟甲烷磺酸镱 水合物 Yb 25-28 % (approx.)

Sigma-Aldrich

405329

三氟甲烷磺酸镱 水合物

三氟甲烷磺酸镁 97%

Sigma-Aldrich

337986

三氟甲烷磺酸镁

Alex R Lippert et al.
Journal of the American Chemical Society, 128(46), 14738-14739 (2006-11-16)
Oligosubstituted bullvalones were synthesized in eight steps from 2,6-cycloheptadienone via a unique Lewis acid catalyzed intramolecular cyclopropanation of a stabilized sulfur ylide, leading directly to the tetracyclic cage structure. Upon exposure to base, the substituted bullvalones tautomerized to a hydroxybullvalene
Saya Kakuda et al.
Journal of the American Chemical Society, 137(9), 3330-3337 (2015-02-11)
Mononuclear copper complexes, [(tmpa)Cu(II)(CH3CN)](ClO4)2 (1, tmpa = tris(2-pyridylmethyl)amine) and [(BzQ)Cu(II)(H2O)2](ClO4)2 (2, BzQ = bis(2-quinolinylmethyl)benzylamine)], act as efficient catalysts for the selective two-electron reduction of O2 by ferrocene derivatives in the presence of scandium triflate (Sc(OTf)3) in acetone, whereas 1 catalyzes
Okamoto, Y., et al.
Macromolecular Symposia, 183, 83-83 (2002)
Kazuaki Ishihara et al.
The Journal of organic chemistry, 61(14), 4560-4567 (1996-07-12)
Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic
Giovanni Desimoni et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(12), 3630-3636 (2008-02-29)
The asymmetric Friedel-Crafts reaction between a series of substituted indoles 2 a-l and methyl (E)-2-oxo-4-aryl-3-butenoates 3 a-c has been efficiently catalyzed by the scandium(III) triflate complex of (4'S,5'S)-2,6-bis[4'-(triisopropylsilyl)oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]pyridine (pybox; 1). Substituted 4-(indol-3-yl)-2-oxo-4-arylbutyric acid methyl esters 4 a-n were usually formed
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商品

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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Questions

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  1. 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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  2. 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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