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696188

Sigma-Aldrich

1,3-双（2,4,6-三甲基苯基）-1,3-二氢-2 H -咪唑-2-亚基

97%

别名:

1,3-双(2,4,6-三甲基苯基)咪唑-2-亚基

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$253.00

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250 MG
$103.00
1 G
$253.00

About This Item

经验公式（希尔记法）:
C21H24N2
CAS号:
141556-42-5
分子量:
304.43
MDL编号:
MFCD09265338
UNSPSC代码:
12352005
PubChem化学物质编号:
329761806
NACRES:
NA.22

$103.00

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质量水平

100

方案

97%

表单

powder

反应适用性

reagent type: catalyst

mp

140 °C

储存温度

−20°C

SMILES字符串

Cc1cc(C)c(N2[C]N(C=C2)c3c(C)cc(C)cc3C)c(C)c1

InChI

1S/C21H24N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h7-12H,1-6H3

InChI key

JCYWCSGERIELPG-UHFFFAOYSA-N

相关类别

应用

1,3-双(2,4,6-三甲基苯基)-1,3-二氢-2H-咪唑-2-亚烷基 (IMes) 是亲核的N-杂环卡宾 (NHC) 配体。
它可用于合成：
  • IMes/铑络合物，其可用作将取代芳基和杂芳基硼酸酯选择性加氢生成顺式取代硼化环烷烃的催化剂。[1]
  • IMes/钌络合物 (Cp*Ru(IMes)Cl)(Cp* =η5-C5Me3)，其可用作烯烃关环复分解反应的催化剂。[2]


IMes还可用作芳基氯化物或芳基三氟甲磺酸盐与芳基硼酸的钯催化Suzuki-Miyaura交叉偶联反应中的辅助配体。[3]

象形图

FlameExclamation mark
GHS02,GHS07

警示用语：

Warning

危险分类

Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

4.1B - Flammable solid hazardous materials

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCV8720
MKCV8717
MKCV8716
MKCV8714
MKCS2748

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Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand
Huang J, et al.
Journal of the American Chemical Society, 121(12), 2674-2678 (1999)
Suzuki- Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems
Grasa GA, et al.
Organometallics, 21(14), 2866-2873 (2002)
Gilles Schnee et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(49), 17959-17972 (2015-10-21)
The present contribution reports experimental and theoretical mechanistic investigations on a normal-to-abnormal (C2-to-C4-bonded) NHC rearrangement processes occurring with bulky group 13 metal NHC adducts, including the scope of such a reactivity for Al compounds. The sterically congested adducts (nItBu)MMe3 (nItBu=1,3-di-tert-butylimidazol-2-ylidene;
Hydrogenation of (Hetero) aryl Boronate Esters with a Cyclic (Alkyl)(amino) carbene-Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles
Ling L, et al.
Angewandte Chemie (International Edition in English), 58(20), 6554-6558 (2019)
Thi Kim Hoang Trinh et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(39), 9242-9252 (2019-04-26)
In the search of smarter routes to control the conditions of N-heterocyclic carbene (NHCs) formation, a two-component air-stable NHC photogenerating system is reported. It relies on the irradiation at 365 nm of a mixture of 2-isopropylthioxanthone (ITX) with 1,3-bis(mesityl)imidazoli(ni)um tetraphenylborate. The

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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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  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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