5-NITROTHIOPHENE-2-CARBONITRILE Chemical Properties

Melting point:

42-46 °C

Boiling point:

273.9±25.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

White to yellow Solid

BRN 

123934

InChI

InChI=1S/C5H2N2O2S/c6-3-4-1-2-5(10-4)7(8)9/h1-2H

InChIKey

FLYONFCGDKAMIH-UHFFFAOYSA-N

SMILES

C1(C#N)SC([N+]([O-])=O)=CC=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/37/39

RIDADR 

UN 3439 6.1/PG 3

WGK Germany 

3

F 

10-13-23

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-NITROTHIOPHENE-2-CARBONITRILE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-nitrothiophene-2-carbonitrile from the compound (CAS: 6030-18-8): oxime (1.0 mmol) and 2-nitrobenzenesulfonate (1.5 mmol) were dissolved in anhydrous dichloromethane (5.0 mL) under nitrogen protection in an oven-drying 50 mL round-bottomed flask fitted with a stirrer. The reaction mixture was stirred at room temperature for 5 min and then 1,8-diazabicycloundec-7-ene (DBU, 2.5 mmol) was slowly added dropwise over 2 min. Upon completion of the dropwise addition, the reaction mixture changed to a clarified homogeneous solution. The reaction process was monitored by thin layer chromatography (TLC). After complete consumption of the starting material, the reaction mixture was diluted with ethyl acetate and washed sequentially with water (2 × 5 mL) and brine (2 × 5 mL). The product was purified by column chromatography. The by-product Oxyma can be recovered by acidifying the aqueous layer followed by extraction with ethyl acetate. The recovered Oxyma can be used to regenerate Oxyma sulfonate, which in turn can be used in another batch reaction.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 33, p. 4397 - 4400
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3173 - 3174,2
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3173 - 3174

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