Skip to Content
Merck
All Photos(1)

Documents

498033

Sigma-Aldrich

Cyclohexylzinc bromide solution

0.5 M in THF

Synonym(s):

Cyclohexylzinc(II)bromide

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

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

Quality Level

100

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

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

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)

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