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498521

Sigma-Aldrich

3-Ethoxy-3-oxopropylzinc bromide solution

0.5 M in THF

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Synonym(s):
(2-Ethoxycarbonylethyl)zinc bromide, (3-Ethoxy-3-oxopropyl)zinc(II)bromide, 3-Ethoxy-3-oxopropylzinc bromide
Linear Formula:
C2H5O2CCH2CH2ZnBr
CAS Number:
Molecular Weight:
246.42
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

0.5 M in THF

density

0.972 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CCOC(=O)CC[Zn]Br

InChI

1S/C5H9O2.BrH.Zn/c1-3-5(6)7-4-2;;/h1,3-4H2,2H3;1H;/q;;+1/p-1

InChI key

XLKAROLEWCMBDC-UHFFFAOYSA-M

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B77207C81217680966
1-Bromo-3-phenylpropane 98%

B77207

1-Bromo-3-phenylpropane

3-Bromo-1-phenyl-1-propene 97%

C81217

3-Bromo-1-phenyl-1-propene

2-Propylzinc bromide solution 0.5 M in THF

680966

2-Propylzinc bromide solution

density

0.972 g/mL at 25 °C

density

1.31 g/mL at 25 °C (lit.)

density

1.332 g/mL at 25 °C (lit.)

density

0.963 g/mL at 25 °C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

concentration

0.5 M in THF

concentration

-

concentration

-

concentration

0.5 M in THF

Application

3-Ethoxy-3-oxopropylzinc bromide is a reagent used to insert ethyl propanoate group to the substrate. It can be used in:
  • Synthesis of γ-keto esters from aryl chlorides.
  • Synthesis of sulfones from 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and alkyl halides.
  • Negishi cross-couplings with aryl vinyl phosphates to synthesize 1,1-disubstituted alkenes.

Legal Information

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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17.0 °C - closed cup


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Investigations on the Suzuki? Miyaura and Negishi Couplings with Alkenyl Phosphates: Application to the Synthesis of 1, 1-Disubstituted Alkenes.
Hansen A L, et al.
The Journal of Organic Chemistry, 72(17), 6464-6472 (2007)
Synthesis of the Novel Tetrahydropyrazolo [3, 4-c] pyridin-5-one Scaffold.
Howe N J, et al.
Synlett, 26(02), 228-232 (2015)
Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides.
Rocke B N, et al.
Organic Letters, 16(1), 154-157 (2013)

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