5,6-Dimethylbenzimidazole

5,6-Dimethylbenzimidazole is a natural benzimidazole derivative. It is a component of vitamin B12 where it serves as a ligand for the cobalt atom.[1]

5,6-Dimethylbenzimidazole
Names
Preferred IUPAC name
5,6-Dimethyl-1H-benzimidazole
Identifiers
3D model (JSmol)
116595
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.627
EC Number
  • 209-488-1
279255
KEGG
UNII
  • InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)
    Key: LJUQGASMPRMWIW-UHFFFAOYSA-N
  • InChI=1/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)
    Key: LJUQGASMPRMWIW-UHFFFAOYAV
  • CC1=CC2=C(C=C1C)N=CN2
Properties
C9H10N2
Molar mass 146.193 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335, H412
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5,6-Dimethylbenzimidazole is biosynthesized from flavin mononucleotide by the enzyme 5,6-dimethylbenzimidazole synthase.[2]

References
  1. Barker, HA; Smyth, RD; Weissbach, H; Toohey, JI; Ladd, JN; Volcani, BE (1960). "Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole". The Journal of Biological Chemistry. 235 (2): 480–8. doi:10.1016/S0021-9258(18)69550-X. PMID 13796809.
  2. "5,6-Dimethylbenzimidazole biosynthesis". MetaCyc.


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