4-Chloromercuribenzoic acid

4-Chloromercuribenzoic acid[1]
Names
IUPAC name
(4-Carboxyphenyl)chloromercury
Other names
p-Chloromercurybenzoic acid; p-Chloromercuribenzoate; 4-Chloromercuribenzoate
Identifiers
CAS Number
3D model (JSmol)
Abbreviations PCMB
Beilstein Reference
 3662892
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.402
EC Number
  • 200-442-6
Gmelin Reference
 261316
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5O2.ClH.Hg/c8-7(9)6-4-2-1-3-5-6;;/h2-5H,(H,8,9);1H;/q;;+1/p-1 checkY
    Key: YFZOUMNUDGGHIW-UHFFFAOYSA-M checkY
  • InChI=1/C7H5O2.ClH.Hg/c8-7(9)6-4-2-1-3-5-6;;/h2-5H,(H,8,9);1H;/q;;+1/p-1/rC7H5ClHgO2/c8-9-6-3-1-5(2-4-6)7(10)11/h1-4H,(H,10,11)
    Key: YFZOUMNUDGGHIW-PSWPUYSSAS
SMILES
  • O=C(O)c1ccc([Hg]Cl)cc1
Properties
Chemical formula
 C7H5ClHgO2
Molar mass 357.16 g·mol−1
Melting point 287 °C (549 °F; 560 K) (dec.)
Hazards
GHS labelling:
Pictograms
 GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word
 Danger
Hazard statements
 H300, H310, H330, H373, H410
Precautionary statements
 P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P330, P361, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Chloromercuribenzoic acid (p-chloromercuribenzoic acid, PCMB) is an organomercury compound that is used as a protease inhibitor, especially in molecular biology applications.

PCMB reacts with thiol groups in proteins and is therefore an inhibitor of enzymes that are dependent on thiol reactivity, including cysteine proteases such as papain and acetylcholinesterase. Because of this reactivity with thiols, PCMB is also used in titrimetric quantification of thiol groups in proteins.

Preparation

4-Chloromercuribenzoic acid can be prepared by oxidation of 4-chloromercuritoluene using potassium permanganate.[2] 4-chloromercuritoluene is in turn obtained by the chloromercuration of sodium toluene sulfinite:[3]

CH3C6H4SO2Na + HgCl2 → CH3C6H4HgCl + SO2 + NaCl

See also

References

  1. ^ 4-Chloromercuribenzoic acid at Sigma-Aldrich
  2. ^ Whitmore, Frank C.; Hamilton, Frances H.; Thurman, N. (1927). "P-Chloromercuribenzoic ACID". Organic Syntheses. 7: 18. doi:10.15227/orgsyn.007.0018.
  3. ^ Whitmore, Frank C.; Woodward, Gladys E. (1923). "p-Tolyl Chloride CHLORIDE". Organic Syntheses. 3: 99. doi:10.15227/orgsyn.003.0099.
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