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499307

Sigma-Aldrich

Phenethylzinc bromide solution

0.5 M in THF

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About This Item

Linear Formula:
C6H5CH2CH2ZnBr
CAS Number:
308796-14-7
Molecular Weight:
250.45
MDL number:
MFCD01311437
UNSPSC Code:
12352103
PubChem Substance ID:
24873270
NACRES:
NA.22

concentration

0.5 M in THF

bp

65 °C

density

0.965 g/mL at 25 °C

functional group

phenyl

storage temp.

2-8°C

SMILES string

Br[Zn]CCc1ccccc1

InChI

1S/C8H9.BrH.Zn/c1-2-8-6-4-3-5-7-8;;/h3-7H,1-2H2;1H;/q;;+1/p-1

InChI key

SEXSOTWHLBYVNF-UHFFFAOYSA-M

Application

Phenethylzinc bromide can be used as a reagent:
  • In the transition metal-catalyzed Negishi cross-coupling reaction to prepare aryl or heteroaryl derivatives by reacting with organic halides or triflates via carbon-carbon bond formation.
  • To prepare (4-phenyl-1-butyn-1-yl)benzene by reacting with phenylacetylene via palladium-catalyzed cross-coupling reaction.
  • To synthesize benzyl substituted thienopyrimidine derivatives.

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7861
SHBM2073
SHBG9446V
SHBG2048V
SHBF1693V

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Palladium-catalyzed aerobic oxidative cross-coupling reactions of terminal alkynes with alkylzinc reagents
Chen M, et al.
Journal of the American Chemical Society, 132(12), 4101-4103 (2010)
Non-peptidic small molecule inhibitors of XIAP
Park C-M, et al.
Bioorganic & Medicinal Chemistry Letters, 15(3), 771-775 (2005)
Substituted thieno [2, 3-d] pyrimidines as adenosine A2A receptor antagonists
Shook BC, et al.
Bioorganic & Medicinal Chemistry Letters, 23(9), 2688-2691 (2013)

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