736627
Mesitylcopper(I)
solid
Synonym(s):
(2,4,6-Trimethylphenyl)copper
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About This Item
Empirical Formula (Hill Notation):
C9H11Cu
CAS Number:
Molecular Weight:
182.73
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22
MDL number:
Product Name
Mesitylcopper(I),
SMILES string
Cc1cc(C)c([Cu])c(C)c1
InChI
1S/C9H11.Cu/c1-7-4-8(2)6-9(3)5-7;/h4-5H,1-3H3;
InChI key
BBUKMFLZOHNUQU-UHFFFAOYSA-N
form
solid
reaction suitability
core: copper, reagent type: catalyst
mp
184-191 °C
storage temp.
2-8°C
Quality Level
Related Categories
General description
Mesitylcopper(I) is a thermally stable and highly soluble organocopper compound, which is commonly used as a metalation reagent in organic synthesis. In mixed lithium cuprate reagents, mesitylcopper serves as a useful ″holding group″. It is very sensitive to moisture and air therefore reactions must be carried out under anhydrous conditions.
Application
Mesitylcopper(I) is can be used to synthesize:
It can also be used as a selective mesityl group transfer reagent in stoichiometric C−C and C−heteroatom bond-forming reactions.
- Homo and heteroleptic copper(I) complexes such as Cu(I) alkoxides, siloxides, phosphates, amides, and phosphides.
- Biorelevant copper(I) complexes as biomimetic model compounds.
- Copper nanoparticles from stabilizing primary amines.
It can also be used as a selective mesityl group transfer reagent in stoichiometric C−C and C−heteroatom bond-forming reactions.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Find documentation for the products that you have recently purchased in the Document Library.
Mesitylcopper-a powerful tool in synthetic chemistry
Stollenz M and Meyer F
Organometallics, 31(22), 7708-7727 (2012)
Preparation of thermally stable and soluble mesitylcopper (I) and its application in organic synthesis
Tsuda T, et al.
The Journal of Organic Chemistry, 46(1), 192-194 (1981)
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