Dibenzylmercury

Base Information

• Chemical Name: Dibenzylmercury
• CAS No.: 780-24-5
• Molecular Formula: C14H14 Hg
• Molecular Weight: 382.855
• DSSTox Substance ID: DTXSID50228651
• Mol file: 780-24-5.mol

Synonyms:Dibenzylmercury;780-24-5;Mercury,bis(phenylmethyl)-;MERCURY, DIBENZYL-;Mercury, bis(phenylmethyl)-;Mercury dibenzyl;BRN 3606128;AI3-19390;4-16-00-01706 (Beilstein Handbook Reference);Mercury, dibenzyl-,;DTXSID50228651;MFCD00014429;AKOS015839031;AS-58935;LS-89745;FT-0632951

Chemical Property of Dibenzylmercury

Chemical Property:

• Melting Point: 108-110°C
• PSA: 0.00000
• LogP: 4.00210
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 384.080194
• Heavy Atom Count: 15
• Complexity: 137

Purity/Quality:

98%Min ^*data from raw suppliers

DIBENZYLMERCURY 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metals, Organic Compounds
• Canonical SMILES: C1=CC=C(C=C1)C[Hg]CC2=CC=CC=C2

Technology Process of Dibenzylmercury

There total 19 articles about Dibenzylmercury which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

potassium tert-butylate (865-47-4) + benzylmercury(II) chloride (2117-39-7) + phosphonic acid diethyl ester (762-04-9) → dibenzylmercury(II) (780-24-5)

Guidance literature:

In dimethyl sulfoxide; Hg deriv. adding to a stirred soln. of potassium tert-butoxide and diethyl phosphite in N2-purged DMSO, stirring for 5 min;

DOI:10.1016/S0022-328X(00)86809-6

Reference yield: 78.0%

mercury(I) chloride (104923-33-3) + benzyl(bromo)zinc (62673-31-8) → dibenzylmercury(II) (780-24-5)

Guidance literature:

In tetrahydrofuran; addn. of dry THF to Hg2Cl2 (4 mmol) in three-necked flask (flushed with Ar); cooling to -50°C; dropwise addn. of soln. of C6H5CH2ZnBr (10 mmol) in THF; stirring for 0.5 h at -50°C, warming to room temp.; stirring for 2 h;; addn. of aq. NH4Cl, extg. with ether (3 times); washing combined org. layers succesively with H2O and brine, drying over MgSO4; evapg. solvents; flash chromy. of crude product; 95% purity (2% (C6H5(CH2)3)2Hg impurity);;

DOI:10.1016/0022-328X(92)88002-Z

Reference yield: 17.0%

benzyl bromide (100-39-0) + mercury → dibenzylmercury(II) (780-24-5) + PhCH2HgBr (4109-72-2)

Guidance literature:

With catalyst: Et₄NBr; In N,N-dimethyl-formamide; mixt. of benzyl bromide and Hg in satd. soln. of Et4NBr in dry DMF agitated (sealed ampoule, Ar, in the dark, 100 h);; ppt. filtered off, washed with ether, dried, (chromy. of the mother liquor: silica gel, CHCl3-hexane (2:1), protected from light);;

DOI:10.1007/BF00947734

upstream raw materials:

phenylmagnesium bromide

bromo(phenyl)mercury

benzylmercury(II) chloride

benzylphenylmercury

Downstream raw materials:

benzyllithium

Methyl-benzyl-chlorphosphin

C₈H₁₀AsCl

methyl-dibenzyl-arsine

Refernces

• 1、 Rozema, Michael J.,Rajagopal, Duddu,Tucker, Charles E.,Knochel, Paul. "Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secondary alcohols". . p. 11 - 27. Retrieved 2007/10/02.