(2-THIENYLMETHYLENE)METHANE-1,1-DICARBONITRILE Chemical Properties

Melting point:

91 °C

Boiling point:

308.6±27.0 °C(Predicted)

Density 

1.302±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

Safety Information

HazardClass 

IRRITANT

(2-THIENYLMETHYLENE)METHANE-1,1-DICARBONITRILE Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 14, p. 790, 1949 DOI: 10.1021/jo01157a011

Synthesis

The general procedure for the synthesis of (2-thienylmethylene)methane-1,1-dicarbonitrile from 2-thiophenecarboxaldehyde and malononitrile was as follows: 5.068 g (50 mmol) of 2-thiophenecarboxaldehyde (I-10) and 0.5 g (5 mol%) of Ru/C catalyst were added to a reaction flask. Subsequently, 3.303 g (50 mmol) of malononitrile (II) and 100 mL of ethanol were added and the reaction was stirred for 15 hours at room temperature. The subsequent processing steps were the same as in Example 1. Finally, 7.769 g of the target product was obtained with 97.0% yield and 98.0% purity analyzed by GC-MS.

References

[1] RSC Advances, 2013, vol. 3, # 45, p. 23075 - 23079
[2] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4927 - 4928
[3] Green Chemistry, 2010, vol. 12, # 3, p. 514 - 517
[4] Patent: CN108383755, 2018, A. Location in patent: Paragraph 0076-0079
[5] European Journal of Organic Chemistry, 2004, # 3, p. 546 - 551

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