Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

499021

Sigma-Aldrich

(2-Naphthylmethyl)zinc bromide solution

0.5 M in THF

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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

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.

Signal Word

Danger

Hazard Statements

H225,H319,H335,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCL2568
SHBC5490
19013LU
16716AO

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service