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21211-65-4

21211-65-4 Structure

21211-65-4 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
[HS Code ]

2933.99.8290
Hazard InformationBack 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]

Pyrrole

109-97-7

Formaldehyde

50-00-0

2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole

21211-65-4

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
Spectrum DetailBack Directory
[Spectrum Detail]

2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole(21211-65-4)1HNMR
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