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710326

Sigma-Aldrich

(1,3-Dioxolan-2-ylmethyl)zinc bromide

0.6 M in THF

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About This Item

Empirical Formula (Hill Notation):
C4H7BrO2Zn
Molecular Weight:
232.39
MDL number:
MFCD07698709
UNSPSC Code:
12352005
PubChem Substance ID:
329762915
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reaction type: C-C Bond Formation

concentration

0.6 M in THF

density

0.992 g/mL at 25 °C

functional group

ether

storage temp.

2-8°C

SMILES string

Br[Zn]CC1OCCO1

InChI

1S/C4H7O2.BrH.Zn/c1-4-5-2-3-6-4;;/h4H,1-3H2;1H;/q;;+1/p-1

InChI key

LOJRLQRGBKTHDB-UHFFFAOYSA-M

Related Categories

General description

(1,3-Dioxolan-2-ylmethyl)zinc bromide is an organozinc compound used as a reagent in Negishi cross-coupling reaction to prepare aryl or heteroaryl scaffolds via C-C bond formation.

Application

(1,3-Dioxolan-2-ylmethyl)zinc bromide can be used as a reagent in the allylic alkylation reactions in the presence of iridium catalyst.

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-22.0 °F

Flash Point(C)

-30 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6264
SHBK8351
SHBF7227V
SHBD8067V
SHBD2485V

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Synthesis of 8-C-substituted 2, 6-diaminopurine acyclic nucleoside phosphonates by Negishi cross-coupling
Sedlavcek O, et al.
Collection of Czechoslovak Chemical Communications, 10(26), 449-450 (2015)
Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides
Hamilton JY, et al.
Angewandte Chemie (International ed. in English), 54(26), 7644-7647 (2015)

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