24423-70-9

Basic information

• Product Name: bis(cyclohexylmethyl)mercury
• CAS NO: 24423-70-9
• Molecular Weight: 394.95
• Mol File: 24423-70-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: bis(cyclohexylmethyl)mercury(CAS DataBase Reference)
• NIST Chemistry Reference: bis(cyclohexylmethyl)mercury(24423-70-9)
• EPA Substance Registry System: bis(cyclohexylmethyl)mercury(24423-70-9)

Safety Data

• Hazardous Substances Data: 24423-70-9(Hazardous Substances Data)

Upstream product

• 4819-11-8 bis(iodomethyl)mercury 
• 121883-35-0 cyclohexylzinc iodide 

Downstream Products

• 24423-78-7 1-(Brommethyl)-1-(dichlormethyl)-cyclohexan 

Relevant articles and documents

Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secondary alcohols

Two new methods of preparation of functionalized diorganomercurials have been developed.The first method involves a substitution reaction of (ICH2)2Hg with zinc-copper reagents FG-RCu(CN)ZnI in THF/DMF at -60 deg C.Functional groups such as an ester, nitrile, ketone, phosphonate, halide, and boronic ester are tolerated in this reaction.The second method involves a reductive transmetallation between polyfunctional organozinc halides and mercurous chloride (Hg2Cl2).This very convenient procedure provides a rapid route to various functionalized diorganomercurials in good yields (61-89percent yield).The synthetic utility of these mercury organometallics is demonstrated.Their transmetallation with zinc dust (toluene, 80 deg C, 3-5 h) affords dialkylzincs which add enantioselectively to aldehydes in the presence of a catalytic amount (20 molpercent) of the norephedrine derivative 13.This transmetallation can also be used to prepare stereoselectively (E)-alkenylzinc halides (> 98percent E).Addition of Cl(H)ZrCp2 to (E)-5-chloropentenylzinc bromide in CH2Cl2 (25 deg C, 1 min) affords a 1,1-bimetallic of zinc and zirconium Cl(CH2)4CH(ZnBr)ZrCp2(Cl) which reacts stereoselectively with an aldehyde providing the (E)-disubstituted olefin (49percent yield; 100percent E).