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498475

Sigma-Aldrich

4-(Ethoxycarbonyl)phenylzinc iodide solution

0.5 M in THF

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About This Item

Linear Formula:
C2H5O2CC6H4ZnI
CAS Number:
131379-16-3
Molecular Weight:
341.46
MDL number:
MFCD00671982
UNSPSC Code:
12352103
PubChem Substance ID:
24873201
NACRES:
NA.22

concentration

0.5 M in THF

density

1.018 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CCOC(=O)c1ccc([Zn]I)cc1

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

InChI key

QKMCGFIQAJUQIL-UHFFFAOYSA-M

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.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.0 °F - closed cup

Flash Point(C)

-17.2 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pd-catalyzed cross-coupling of functionalized organozinc reagents with thiomethyl-substituted heterocycles
Metzger A, et al.
Organic Letters, 11(18), 4228-4231 (2009)
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)
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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