Phenyl(tribromomethyl)mercury

Base Information

• Chemical Name: Phenyl(tribromomethyl)mercury
• CAS No.: 3294-60-8
• Molecular Formula: C7H5 Br3 Hg
• Molecular Weight: 529.419
• Hs Code.: 2931900090
• European Community (EC) Number: 221-963-5
• NSC Number: 173931
• DSSTox Substance ID: DTXSID20186592
• Mol file: 3294-60-8.mol

Synonyms:Phenyl(tribromomethyl)mercury;3294-60-8;EINECS 221-963-5;NSC173931;C7H5Br3Hg;C(Br)(Br)Br.c1ccccc1;C7-H5-Br3-Hg;SCHEMBL6968552;Mercury, phenyl(tribromomethyl)-;DTXSID20186592;NSC 173931;NSC-173931;NCI60_001412

Chemical Property of Phenyl(tribromomethyl)mercury

Chemical Property:

• Melting Point: 119-120 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 3.61030
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 529.76273
• Heavy Atom Count: 11
• Complexity: 115

Purity/Quality:

PHENYL(TRIBROMOMETHYL)MERCURY 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[Hg]C(Br)(Br)Br
• General Description: Phenyl(tribromomethyl)mercury is a mercury-based reagent that serves as a source of dibromocarbene, which is utilized in the deoxygenation of aldehydes and ketones. This reaction proceeds via the formation of carbonyl ylides, which subsequently rearrange to produce carbon monoxide and dihalides. The reagent demonstrates broad reactivity, effectively deoxygenating both aliphatic and aromatic carbonyl compounds under mild conditions (75–80°C in benzene), making it a versatile tool in synthetic organic chemistry for carbonyl deoxygenation.

Technology Process of Phenyl(tribromomethyl)mercury

There total 2 articles about Phenyl(tribromomethyl)mercury 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: 95.0%

Bromoform (75-25-2) + phenylmercury(II) chloride (100-56-1) → phenyl(tribromomethyl)mercury(II) (3294-60-8)

Guidance literature:

With potassium hydroxide; In Bromoform; water; an aq. KOH soln. was added to react. mixt. at 25 °C, stirred 2 h; washed (H2O), extd. (Et2O), org. layer was dried (anhyd. MgSO4), filtered, solvent was removed by rotary evapn., recrystd. (Et2O/petroleum ether); elem. anal.;

Reference yield:

→ phenyl(tribromomethyl)mercury(II) (3294-60-8)

Guidance literature:

DOI:10.1016/S0022-328X(00)81631-9

Reference yield: 92.0%

phenyl(tribromomethyl)mercury(II) (3294-60-8) + 3-((1S,2S,6R,8R,11R)-8-Benzyloxymethyl-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-4-en-11-yl)-propionic acid ethyl ester → C26H32Br2O5

Guidance literature:

In benzene; at 80 ℃;

DOI:10.1021/ja00248a042

upstream raw materials:

Bromoform

phenylmercury(II) chloride

Downstream raw materials:

Brommethyl-triethylsilan

dimethyl 2-bromomalonate

1,1-Dibrom-2-fluor-cyclopropan

1,1-Dibrom-2-fluor-2-methyl-cyclopropan

Refernces

DEOXYGENATION OF ALDEHYDES AND KETONES; A NEW GENERAL REACTION OF DIBROMOCARBENE AND DIBROMOCARBONYL YLIDES

10.1016/S0040-4039(00)88035-1

The research investigates the deoxygenation of aldehydes and ketones using phenyl(tribromomethyl)mercury, which generates dibromocarbene. This study demonstrates that the formation of carbon monoxide from the reaction of dibromocarbene with various aldehydes and ketones is a general reaction, contrary to earlier suggestions that mercurial carbene precursors might not react with simple aliphatic ketones. The key chemicals involved in this research include phenyl(tribromomethyl)mercury as the source of dibromocarbene, a variety of aldehydes such as benzaldehyde and propionaldehyde, and ketones like acetone, cyclohexanone, and norcamphor. The reaction typically involves treating these carbonyl compounds with phenyl(tribromomethyl)mercury in benzene at 75-80°C for 4 hours, resulting in the production of carbon monoxide with yields ranging from about 16% to 46%. The study also explores the mechanistic aspects of the reaction, suggesting that the formation of carbon monoxide involves the rearrangement of an initially formed carbonyl ylide to alkoxyhalocarbene, followed by the formation of dihalide and CO.