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498033

Sigma-Aldrich

Cyclohexylzinc bromide solution

0.5 M in THF

Synonym(s):

Cyclohexylzinc(II)bromide

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About This Item

Linear Formula:
C6H11ZnBr
CAS Number:
7565-57-3
Molecular Weight:
228.45
MDL number:
MFCD00671993
UNSPSC Code:
12352103
PubChem Substance ID:
24873165
NACRES:
NA.22

concentration

0.5 M in THF

density

0.963 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Zn]C1CCCCC1

InChI

1S/C6H11.BrH.Zn/c1-2-4-6-5-3-1;;/h1H,2-6H2;1H;/q;;+1/p-1

InChI key

XHGMTEIVIUFIPO-UHFFFAOYSA-M

Application

Cyclohexylzinc bromide is an organozinc reagent, generally used in Negishi coupling. Examples include the cross-coupling of alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent and nickel-catalyzed synthesis of 4-substituted coumarins.

It can react with the SO2 surrogate, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) to afford zinc sulfinate salts which can be alkylated to synthesize various useful sulfones.

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 Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - 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)

3.0 °F - closed cup

Flash Point(C)

-16.1 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN3529
SHBJ2877
SHBH4395V
SHBF9141V
SHBF5892V

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Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent.
Calimsiz S and Organ M G
Chemical Communications (Cambridge, England), 47(18), 5181-5183 (2011)
Nickel-Catalyzed Cross-Couplings of 4-Diethylphosphonooxycoumarins with Organozinc Reagents: An Efficient New Methodology for the Synthesis of 4-Substituted Coumarins.
Wu J and Yang Z
The Journal of Organic Chemistry, 66(23), 7875-7878 (2001)
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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