| Identification | Back Directory | [Name]
2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole | [CAS]
21211-65-4 | [Synonyms]
ipyrromethane
dipyrroMethane
dipyrrolylmethane
Di(1H-pyrrol-2-yl)
Di-2-pyrrolylmethane
2,2'-Dipyrrolylmethane
Di(1H-pyrrol-2-yl)Methane
2,2'-Dipyrrolylmethane>
1H-Pyrrole, 2,2'-Methylenebis-
2,2'-Methanediylbis(1H-pyrrole)
2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole ISO 9001：2015 REACH | [Molecular Formula]
C9H10N2 | [MDL Number]
MFCD03931560
| [MOL File]
21211-65-4.mol | [Molecular Weight]
146.19 |
| Chemical Properties | Back Directory | [Melting point ]
72.0 to 77.0 °C | [Boiling point ]
120°C/2mmHg(lit.) | [density ]
1.0976 (rough estimate) | [refractive index ]
1.5600 (estimate) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
Chloroform, Methanol | [form ]
Solid | [pka]
17.25±0.50(Predicted) | [color ]
Green Grey | [λmax]
449nm(CHCl3)(lit.) | [InChI]
InChI=1S/C9H10N2/c1-3-8(10-5-1)7-9-4-2-6-11-9/h1-6,10-11H,7H2 | [InChIKey]
PBTPREHATAFBEN-UHFFFAOYSA-N | [SMILES]
C(C1=CC=CN1)C1=CC=CN1 |
| Hazard Information | Back Directory | [Chemical Properties]
gray solid | [Uses]
Dipyrromethane is a new organic reagent for the synthesis of gold nanoparticles. | [Definition]
ChEBI: Dipyrromethane is a dipyrrole. | [Synthesis]
The general procedure for the synthesis of di(1H-pyrrol-2-yl)methane from pyrrole and formaldehyde was as follows: paraformaldehyde (0.5 g, 16.7 mmol) was added to pyrrole (118 mL, 1.67 mol) as a solvent, followed by the addition of catalyst indium(III) chloride (370 mg, 1.67 mmol). The reaction mixture was stirred at room temperature for 10 h under argon protection. Subsequently, the reaction system was warmed up to 55 °C and stirring was continued for 6 hours. After completion of the reaction, sodium hydroxide (NaOH, 0.2 g, 83.5 mmol) was added and stirred for 4 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography using dichloromethane: hexane (1:1, v/v) as eluent to afford 2.05 g (yield: 84%) of the target compound di(1H-pyrrol-2-yl)methane as a white solid. | [References]
[1] Tetrahedron, 2011, vol. 67, # 26, p. 4924 - 4932
[2] Monatshefte fur Chemie, 2004, vol. 135, # 10, p. 1265 - 1273
[3] Patent: KR101545325, 2015, B1. Location in patent: Paragraph 0096-0100
[4] Journal of the American Chemical Society, 2014, vol. 136, # 51, p. 17802 - 17807
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 2, p. 691 - 695 |
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