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499021 Sigma-Aldrich

(2-Naphthylmethyl)zinc bromide solution

0.5 M in THF

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Properties

Related Categories Alkyl, Chemical Synthesis, Organometallic Reagents, Organozinc Halides, Rieke and Organozinc Reagents More...
Quality Level   100
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

Description

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.

Packaging

50 mL in Sure/Seal™

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Supplemental Hazard Statements 
EUH018 - EUH019
RIDADR 
UN 2924 8(3) / PGII
WGK Germany 
WGK 3
Flash Point(F) 
1.4 °F - closed cup
Flash Point(C) 
-17 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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