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499021

Sigma-Aldrich

(2-Naphthylmethyl)zinc bromide solution

0.5 M in THF

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About This Item

Linear Formula:
C10H7CH2ZnBr
CAS Number:
152329-44-7
Molecular Weight:
286.48
MDL number:
MFCD01311438
UNSPSC Code:
12352103
PubChem Substance ID:
24873248
NACRES:
NA.22

concentration

0.5 M in THF

density

0.978 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Zn]Cc1ccc2ccccc2c1

InChI

1S/C11H9.BrH.Zn/c1-9-6-7-10-4-2-3-5-11(10)8-9;;/h2-8H,1H2;1H;/q;;+1/p-1

InChI key

IKDINBHMSAHXCA-UHFFFAOYSA-M

General description

(2-Naphthylmethyl)zinc bromide is an organozinc halide, which is typically used as a reagent in Negishi cross-coupling reactions. In this process, the organozinc halide reacts with organic halides or triflates to form a carbon-carbon bond in the presence of a Pd catalyst.

Application

(2-Naphthylmethyl)zinc bromide can be used as a reagent for the synthesis of:
  • 4-(5,6-dimethoxy-2-(naphthalen-2-ylmethyl)pyridin-3-yl)benzonitrile from 4-(2-bromo-5,6-dimethoxypyridin-3-yl)benzonitrile using Pd catalyst.
  • (E)-stilbene, (2,2′-[1,4-phenylenedi-(1E)-2,1-ethenediyl]bis[naphthalene]) from 1,4-benzenedicarboxaldehyde in the presence of Pd catalyst and a silylating agent.

Legal Information

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

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °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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Recent developments in Negishi cross-coupling reactions
Haas D, et al.
ACS Catalysis, 6(3), 1540-1552 (2016)
Palladium-Catalyzed Stereoselective Synthesis of (E)-Stilbenes via Organozinc Reagents and Carbonyl Compounds
Wang J-X, et al.
advanced synthesis and catalysis, 348(10-11), 1262-1270 (2006)
Hye Yeon Sagong et al.
ChemMedChem, 14(12), 1204-1223 (2019-04-16)
Seasonal influenza infections are associated with an estimated 250-500 000 deaths annually. Resistance to the antiviral M2 ion-channel inhibitors has largely invalidated their clinical utility. Resistance to neuraminidase inhibitors has also been observed in several influenza A virus (IAV) strains. These data
Palladium-Catalyzed Stereoselective Synthesis of (E)-Stilbenes via Organozinc Reagents and Carbonyl Compounds
Wang J-X, et al.
Advanced Synthesis & Catalysis, 348(10-11), 1262-1270 (2006)

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