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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%

同義詞:

1,3-双(2,4,6-三甲基苯基)咪唑-2-亚基

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About This Item

經驗公式（希爾表示法）:
C21H24N2
CAS號碼:
141556-42-5
分子量：:
304.43
MDL號碼:
MFCD09265338
分類程式碼代碼:
12352005
PubChem物質ID:
329761806
NACRES:
NA.22
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化驗

97%

形狀

powder

反應適用性

reagent type: catalyst

mp

140 °C

儲存溫度

−20°C

SMILES 字串

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 密鑰

JCYWCSGERIELPG-UHFFFAOYSA-N

相關類別

應用

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]

象形圖

FlameExclamation mark
GHS02,GHS07

訊號詞

Warning

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

4.1B - Flammable solid hazardous materials

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

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

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
MKCV8720
MKCV8717
MKCV8716
MKCV8714
MKCS2748

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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;
Suzuki- Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems
Grasa GA, et al.
Organometallics, 21(14), 2866-2873 (2002)
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)
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)
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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