5-NITROTHIOPHENE-2-CARBOXALDEHYDE Chemical Properties

Melting point:

75-77 °C (lit.)

Boiling point:

118-120 °C(Press: 3-4 Torr)

Density 

1.534±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

acetone: soluble1%, clear, yellow

form 

Solid

color 

Brown

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

120540

InChI

InChI=1S/C5H3NO3S/c7-3-4-1-2-5(10-4)6(8)9/h1-3H

InChIKey

CHTSWZNXEKOLPM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4521-33-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29349990

MSDS

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

5-NITROTHIOPHENE-2-CARBOXALDEHYDE Usage And Synthesis

Uses

5-Nitrothiophene-2-carboxaldehyde is a reagent that is used in the activity of mefloquine-oxazolidine derivatives against multidrug-resistant Mycobacterium tuberculosis.

Uses

5-Nitro-2-thiophenecarboxaldehyde was used in preparation of 2, 3-dihydro-2-(5-nitro-2-thienyl) quinazolin-4-(1H)-ones and various novel oxime ether derivatives, anti-protozoan agents.

General Description

Diastereoselectivity in [4+2] cycloaddition of 1-methoxy-2-methyl-3-(trimethylsiloxy)-1,3-pentadiene with 5-nitro-2-thiophenecarboxaldehyde was investigated.

Synthesis

General procedure for the synthesis of 5-nitrothiophene-2-carbaldehyde and 4-nitrothiophene-2-carbaldehyde from 2-thiophenecarboxaldehyde: Step 1: Synthesis of 4-nitrothiophene-2-carbaldehyde (1) Fuming nitric acid (40 mL) was mixed with concentrated sulfuric acid (31 mL) and slowly added to a cooled solution of thiophene-2-carbaldehyde (20 g, 17.8 mmol) in concentrated sulfuric acid (4 mL). The reaction was carried out in an ice-salt bath and stirring was continued for 5 min after addition. Subsequently, the reaction was quenched by the addition of ice water and the mixture was extracted with ether. The combined ether extracts were washed sequentially with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give a brown oily crude product. 1H NMR analysis of the crude product showed a mixture of 4-nitrothiophene-2-carboxaldehyde and 5-nitrothiophene-2-carboxaldehyde in the ratio of about 40:60. Separation of the mixture by column chromatography (eluent: 30-50% dichloromethane/hexanes) gave 4-nitrothiophene-2-carboxaldehyde in 40% yield as a light yellow solid.1H NMR (CDCl3) δ (ppm). 9.95 (s, 1H), 8.63 (s, 1H), 8.27 (s, 1H).

References

[1] Journal of Chemical Research, Miniprint, 1997, # 9, p. 2001 - 2013
[2] Patent: WO2008/104077, 2008, A1. Location in patent: Page/Page column 46
[3] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 1, p. 162 - 165
[4] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 1378

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