498475
4-(Ethoxycarbonyl)phenylzinc iodide solution
0.5 M in THF
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About This Item
Linear Formula:
C2H5O2CC6H4ZnI
CAS Number:
Molecular Weight:
341.46
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/C9H9O2.HI.Zn/c1-2-11-9(10)8-6-4-3-5-7-8;;/h4-7H,2H2,1H3;1H;/q;;+1/p-1
SMILES string
CCOC(=O)c1ccc([Zn]I)cc1
InChI key
QKMCGFIQAJUQIL-UHFFFAOYSA-M
concentration
0.5 M in THF
density
1.018 g/mL at 25 °C
storage temp.
2-8°C
Application
4-(Ethoxycarbonyl)phenylzinc iodide can be used as:
- A substrate in the transition metal-catalyzed cross-coupling reactions with unsaturated thioethers and thiomethyl-substituted N-heterocycles.
- A starting material in the synthesis of indazole derived glucagon receptor antagonists.
- A substrate in the Pd-catalyzed synthesis of 5-aryl-2-furaldehydes by reacting with 5-bromo-2-furaldehyde.
Legal Information
Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
1.0 °F - closed cup
flash_point_c
-17.2 °C - closed cup
Regulatory Information
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Pd-and Ni-Catalyzed Cross-Coupling Reactions of Functionalized Organozinc Reagents with Unsaturated Thioethers
Melzig L, et al.
Chemistry?A European Journal , 17(10), 2948-2956 (2011)
Pd-catalyzed cross-coupling of functionalized organozinc reagents with thiomethyl-substituted heterocycles
Metzger A, et al.
Organic Letters, 11(18), 4228-4231 (2009)
Discovery of potent and orally bioavailable indazole-based glucagon receptor antagonists for the treatment of type 2 diabetes
Xu G, et al.
Bioorganic & Medicinal Chemistry Letters, 29(20), 126668-126668 (2019)
A convenient synthesis of 5-aryl-and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
Kim S and Rieke RD
Tetrahedron Letters, 51(19), 2657-2659 (2010)
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