| Identification | Back Directory | [Name]
2,2'-BIIMIDAZOLE | [CAS]
492-98-8 | [Synonyms]
NSC 522950
bisimidazole
2,2'-BIIMIDAZOLE
2,2'-Diimidazole
2,2'-Biimidazolyl
2,2'-Bisimidazole
Glycosine of Debus
2,2'-bi-1H-imidazole
LABOTEST-BB LTBB005450
1H,1'H-2,2'-BiiMidazole
1H,1'H-[2,2']BIIMIDAZOLYL
2-(1H-imidazol-2-yl)-1H-imidazole | [EINECS(EC#)]
207-768-8 | [Molecular Formula]
C6H6N4 | [MDL Number]
MFCD00047014 | [MOL File]
492-98-8.mol | [Molecular Weight]
134.14 |
| Chemical Properties | Back Directory | [Melting point ]
>350°C | [Boiling point ]
455.5±28.0 °C(Predicted) | [density ]
1.371±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
pK1: 5.01(+1) (25°C,μ= 0.3) | [color ]
Light yellow to Brown to Dark green | [λmax]
274nm(HCl aq.)(lit.) | [InChI]
InChI=1S/C6H6N4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H,(H,7,8)(H,9,10) | [InChIKey]
AZUHIVLOSAPWDM-UHFFFAOYSA-N | [SMILES]
C1(C2NC=CN=2)NC=CN=1 |
| Hazard Information | Back Directory | [Chemical Properties]
2,2'-Biimidazole is soluble in polar solvents such as methanol, water and dimethyl sulfoxide (DMSO). | [Uses]
1H,1''H-2,2''-Biimidazole is used in the preparation of complexes that exhibits photoluminescence and optical properties. Also used in the preparation of bismuth biimidazoles as semi-conductors. | [Application]
2,2'-Biimidazole is an important organic reagent used as:
(1) Preparation of catalytically active coordination compounds. It is a Lewis base capable of producing coordination compounds with metal ions such as Cu(I), Ag(I), Au(I-II) and palladium, which are used as efficient catalysts in other chemical reactions.
(2) Construction of hypercrosslinked polymers 2,2′-biimidazolyl HCPs, which are used as adsorbents and sensors for iodine capture and DNP detection in the field of environmental remediation.
(3) Synthesis of fluorescent proteins, nanoparticles and other ligand compounds. | [Synthesis]
120 ml of distilled water was added to 1,092 g (14.2 mol, 4.0 eq.) of ammonium acetate at 40 ℃, 500 g of 20 wt percent aqueous glyoxal (3.45 mol) was then slowly added dropwise to the resulting slurry for three hours while stirring vigorously. Immediately after the addition was finished, the reaction mixture was neutralized with distilled water to adjust the pH to 5-7. The produced brown-colored solid was filtered and washed alternately with 500 ml of acetone and 500 ml of distilled water several times to obtain 82.0 g (53.2 percent yield) of 2,2'-Biimidazole.
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