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499005

Sigma-Aldrich

5-Methyl-2-pyridylzinc bromide solution

0.5 M in THF

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About This Item

Empirical Formula (Hill Notation):
C6H6BrNZn
CAS Number:
257876-05-4
Molecular Weight:
237.41
MDL number:
MFCD01311463
UNSPSC Code:
12352103
PubChem Substance ID:
24873246
NACRES:
NA.22

concentration

0.5 M in THF

density

0.959 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Cc1ccc([Zn]Br)nc1

InChI

1S/C6H6N.BrH.Zn/c1-6-3-2-4-7-5-6;;/h2-3,5H,1H3;1H;/q;;+1/p-1

InChI key

ZWOPKPFXOHYOBO-UHFFFAOYSA-M

Application

5-Methyl-2-pyridylzinc bromide can be used as a substrate:
  • In the Pd-catalyzed C-C bond-forming reactions with 3-iodothiophene.[1]
  • In the Pd-catalyzed synthesis of 5-heteroaryl- and 5-aryl-2-furaldehydes by reacting with 5-bromo-2-furaldehyde.[2][3]

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17.0 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ0826
SHBF0510V
SHBC1337
31196AP
21796MM

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2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
Kim S and Rieke RD
Tetrahedron, 66(17), 3135-3146 (2010)
Seung-Hoi Kim et al.
The Journal of organic chemistry, 78(5), 1984-1993 (2012-10-19)
Facile synthetic routes for the preparation of a wide range of 5-substituted 2-furaldehydes have been revealed. They were accomplished through either Pd-catalyzed cross-coupling reaction of various aryl- and heteroarylzinc halides with 5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc
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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