4-Chloromercuribenzoic acid

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4-Chloromercuribenzoic acid [1]
4-chloromercuribenzoic acid.png
4-Chloromercuribenzoic-acid-3D-vdW.svg
Names
IUPAC name
(4-Carboxyphenyl)chloromercury
Other names
p-Chloromercurybenzoic acid; p-Chloromercuribenzoate; 4-Chloromercuribenzoate
Identifiers
3D model (JSmol)
AbbreviationsPCMB
3662892
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.402 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-442-6
261316
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: YFZOUMNUDGGHIW-UHFFFAOYSA-M Yes check.svgY
  • 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
  • O=C(O)c1ccc([Hg]Cl)cc1
Properties
C7H5ClHgO2
Molar mass 357.16 g·mol−1
Melting point 287 °C (549 °F; 560 K) (dec.)
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H300, H310, H330, H373, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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

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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.