Chemistry:Mercaptobenzimidazole

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Mercaptobenzimidazole
Mercaptobenzimidazole.svg
Names
Preferred IUPAC name
1,3-Dihydro-2H-1,3-benzimidazole-2-thione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 604-756-8
  • 209-502-6
RTECS number
  • DE1050000
UNII
UN number 2811
Properties
C7H6N2S
Molar mass 150.20 g·mol−1
Appearance white solid
Density 1.42 g/cm3
Melting point 298 °C (568 °F; 571 K)
Hazards
GHS pictograms GHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Warning
H302, H332, H361, H373, H410
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+312, P304+312, P304+340, P308+313, P312, P314, P330, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mercaptobenzimidazole is the organosulfur compound with the formula C6H4(NH)2C=S. It is the mercaptan of benzimidazole. It is a white solid that has been investigated as a corrosion inhibitor. The name is a misnomer because the compound is a thiourea, characterized with a short C=S bond length of 169 pm.[1] A similar situation applies to 2-mercaptoimidazole, which is also a thiourea properly called 2-imidazolidinethione and mercaptobenzothiazole, which is also a thioamide.

It is prepared from o-phenylenediamine.[2]

References

  1. Form, G. R.; Raper, E. S.; Downie, T. C. (1976). "The crystal and molecular structure of 2-mercaptobenzimidazole". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry 32 (2): 345–348. doi:10.1107/S0567740876003026. 
  2. VanAllan, J. A.; Deacon, B. D. (1950). "2-Mercaptobenzimidazole". Organic Syntheses 30: 56. doi:10.15227/orgsyn.030.0056.