Mercaptobenzimidazole

Last updated
Mercaptobenzimidazole
Mercaptobenzimidazole.svg
Names
Preferred IUPAC name
1,3-Dihydro-2H-1,3-benzimidazole-2-thione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.640 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 604-756-8
  • 209-502-6
PubChem CID
RTECS number
  • DE1050000
UNII
UN number 2811
  • InChI=1S/C7H6N2S/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)
    Key: YHMYGUUIMTVXNW-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)NC(=S)N2
Properties
C7H6N2S
Molar mass 150.20 g·mol−1
Appearancewhite solid
Density 1.42 g/cm3
Melting point 298 °C (568 °F; 571 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H302, H332, H361, H373, H410
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P312, P304+P340, P308+P313, 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).

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]

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Dithiobiuret is an organosulfur compound with the formula HN(C(S)NH2)2. It is a colourless solid that is soluble in warm water and polar organic solvents. It is a planar molecule with short C-S and C-N distances (1.69, 1.38 Å, resp.) indicative of multiple C-S and C-N bonding.

<i>N</i>,<i>N</i>-Di-<i>n</i>-butylthiourea Chemical compound

N,N′-Di-n-butylthiourea is an organic compound with the formula S=C(N(H)Bu)2 (Bu = butyl). A symmetrical N,N′-dialkyl thiourea derivative, it is a white solid. Like other thiourea derivatives, it features a planar core. The C=S bond distance is 1.712(2) Å, while C−N distances are in range of 1.33 to 1.46 Å. Molecules of this compound exhibit syn-anti conformation.

<span class="mw-page-title-main">4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole</span> Chemical compound

4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is an organic compound with the formula SC2N3H(NH2)(N2H3). The compound consists of a 1,2,4-triazole heterocycle with three functional groups: amine, thioamide and hydrazyl. X-ray crystallography shows that this molecule is polar but with a C=S double bond. It is prepared by the reaction of hydrazine with thiourea:

<span class="mw-page-title-main">2-Imidazolidinethione</span> Chemical compound

2-Imidazolidinethione is the organosulfur compound with the formula C2H2(NH)2C=S. It is a cyclic unsaturated thiourea with a short C=S bond length of 169 pm. The compound is often referred to as 2-mercaptoimidazole, which is a tautomer that is not observed. The compound forms a variety of metal complexes. In terms of bonding and reactivity, 2-imidazolidinethione is similar to mercaptobenzimidazole.

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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.