7565-57-3 Usage
Description
Cyclohexylzinc bromide is an organozinc reagent characterized by its ability to participate in various chemical reactions, particularly in the field of organic synthesis. It is known for its reactivity and stability, making it a valuable compound in the synthesis of complex organic molecules.
Uses
Used in Pharmaceutical Industry:
Cyclohexylzinc bromide is used as a key reagent for Negishi coupling, a widely employed method in the synthesis of complex organic molecules, including pharmaceutical compounds. Its application in this industry is crucial for the development of new drugs and the improvement of existing ones.
Used in Chemical Synthesis:
Cyclohexylzinc bromide is used as a coupling agent for the cross-coupling of alkylzinc halides with aryl/heteroaryl halides. This reaction is facilitated by the use of Pd-PEPPSI-IPent, a palladium-based catalyst, which enhances the efficiency and selectivity of the process.
Used in Synthesis of 4-Substituted Coumarins:
In the field of organic chemistry, cyclohexylzinc bromide is used as a reagent in the nickel-catalyzed synthesis of 4-substituted coumarins. These compounds are important due to their diverse applications, including their use as pharmaceuticals, agrochemicals, and dyes.
Used in Synthesis of Sulfone Compounds:
Cyclohexylzinc bromide can react with the SO2 surrogate, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), to afford zinc sulfinate salts. These salts can be further alkylated to synthesize various useful sulfones, which are important intermediates in the production of a wide range of chemical products, including pharmaceuticals and agrochemicals.
Check Digit Verification of cas no
The CAS Registry Mumber 7565-57-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,6 and 5 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 7565-57:
(6*7)+(5*5)+(4*6)+(3*5)+(2*5)+(1*7)=123
123 % 10 = 3
So 7565-57-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H11.BrH.Zn/c1-2-4-6-5-3-1;;/h1H,2-6H2;1H;/q-1;;+2/p-1/rC6H11.BrZn/c1-2-4-6-5-3-1;1-2/h1H,2-6H2;/q-1;+1
7565-57-3Relevant articles and documents
Palladium-catalyzed secondary benzylic imidoylative reactions
Wang, Chenglong,Wu, Licheng,Xu, Wentao,He, Feng,Qu, Jingping,Chen, Yifeng
supporting information, p. 6954 - 6959 (2020/09/15)
Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.
Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide
Fulton, Tyler J.,Alley, Phebe L.,Rensch, Heather R.,Ackerman, Adriana M.,Berlin, Cameron B.,Krout, Michael R.
, p. 14723 - 14732 (2018/11/23)
Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.
