823-04-1

Basic information

• Product Name: PHENYLMERCURIC IODIDE
• Synonyms: PHENYLMERCURIC IODIDE;Iodo(phenyl)mercury;Mercury,iodophenyl-;Phenylmercury(II) iodide
• CAS NO: 823-04-1
• Molecular Formula: C₆H₅HgI
• Molecular Weight: 404.6
• Mol File: 823-04-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PHENYLMERCURIC IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLMERCURIC IODIDE(823-04-1)
• EPA Substance Registry System: PHENYLMERCURIC IODIDE(823-04-1)

Safety Data

• RIDADR: 2026
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 823-04-1(Hazardous Substances Data)

Upstream product

• 98-80-6 phenylboronic acid 
• 587-85-9 diphenylmercury(II) 
• 2097-19-0 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane 
• 7553-56-2 iodine 
• 79293-02-0 CH₃C₆H₄COSHgC₆H₅ 
• 79292-97-0 ClC₆H₄COSHgC₆H₅ 
• 79293-05-3 phenylmercury thiobenzoate 
• 79293-00-8 CH₃OC₆H₄COSHgC₆H₅ 
• 180210-25-7 (C₆H₅)Hg(N₃O₄) 
• 7681-11-0 potassium iodide 
• 960-16-7 tributylphenylstannane 
• 368-47-8 phenyltrifluorosilane 
• 595-90-4 tetraphenyltin(IV) 
• 141-51-5 (Iodomethyl)mercuric iodide 

Downstream Products

• 92-52-4 biphenyl 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 134-85-0 4-chlorobenzophenone 
• 31597-94-1 Hg(C₆H₅)(SC₆F₅) 

Relevant articles and documents

Dinitramide and its salts: 9. Mercury(II) dinitramidate, a new reagent in chemistry of organomercury compounds

The potentialities of synthesis on the basis of mercury(II) dinitramidate Hg(N3O4)2 in mercuration, addition to the double carbon-carbon bond, alkylation, and complexation are shown.

Nucleophilic cleavage of the Si-C bond in organotrifluorosilanes and diorganodifluorosilanes

The Si-C bond in aryltrifluorosilanes, 4-XC6H4SiF3 (X = H, CH3, Cl, Br or NO2), is readily cleaved by mercury(II) salts HgY2 (Y = Cl, Br, I, CN or OCOCH3) or HgO to form organomercurials of the type 4-XC6H4HgY or (4-XC6H4)2Hg, respectively.Electron-donating substituent X facilitate the reaction, whereas electron-withdrawing substituents make it more difficult.Mercury(II) salts and mercury(II) oxide also cleave the Si-C bond in chloromethyltrifluorosilanes, F3Si(CH3-nCln) (n = 1-3) to produce the corresponding organic mercurials containing an Hg(CH3-nCln) group.The substitution of the fluorine atom in organotrifluorosilanes by an alkyl group hinders the bond cleavage between the silicon atom and the electronegative organic substituent.The reactions studied are believed to follow a nucleophilic mechanism involving asynchronous formation of a four-centered transition state with a pentacoordinate silicon atom.

KINETICS AND MECHANISM OF MERCURIDESTANNYLATION OF PHENYLSTANNATRANES AND RELATED DERIVATIVES

The kinetics and mechanism of mercuridestannylation of phenylstannatrane derivatives, PhSn(OCH2CH2)3N and PhSn(OC6H4)3N have been investigated relative to model systems PhSnBu3, PhSn(OMe)3 in solvent MeOH.For the latter two, the reaction proceeded via the

DIRECT TRANSFER OF ALIPHATIC AND AROMATIC SUBSTITUENTS FROM ORGANOSILATRANES TO MERCURY(II) SPECIES

The relative reaction rates of several silatranes (derivatives of 2,8,9-trioxa-5-aza-1-silatricyclo1,5>undecane) and HgCl2 in acetone-d6 to yield the corresponding organomercury compound are of the order of e.g., 5 * 10-1 1 mol-1 sec-1 or slightly less, a rate that is unexpectedly high compared to the essentially inert parent organotrialkoxysilanes.Thus, the apical Si-C bond of the silatrane is extraordinarily susceptible to direct electrophilic attack by mercury(II).The rates decrease in the order CH2=CH, C6H5, p-ClC6H4 > CH3 > CH3CH2, CH3CH2CH2 > C6H11, ClCH2, Cl2CH, CH3CH2O.The effects of varying the solvent and the counterions are noted, and the probable mechanism is discussed.

Bis(Iodomethyl) Mercury as a CH2 Transfer Reagent

Bis(iodomethyl) mercury, Hg(CH2I)2, is an effective transfer agent of one CH2 group to olefins to form cyclopropanes.Transfer of the second group (i.e., from ICH2HgI) is not a favourable process.However, the ICH2HgI/Ph2Hg or the ICH2HgI/(PhCH2)2Hg couples serve to transfer the second CH2 group to olefins.