499021

(2-Naphthylmethyl)zinc bromide solution

0.5 M in THF

• 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

Properties

• 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.

Legal Information

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

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H319,H335,H336,H351
• pcodes: P202 - P210 - P233 - P240 - P305 + P351 + P338 - P308 + P313
• 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