2-CHLORO-3-NITROBENZALDEHYDE Chemical Properties

Boiling point:

293.5±25.0 °C(Predicted)

Density 

1.485±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder

color 

Yellow

Safety Information

HS Code 

2913000090

2-CHLORO-3-NITROBENZALDEHYDE Usage And Synthesis

Synthesis

Step 2. Synthesis of 2-chloro-3-nitrobenzaldehyde: To a 250 mL three-necked round-bottomed flask, a solution of oxalyl chloride (5.42 g, 42.70 mmol, 1.10 eq.) in dichloromethane (DCM, 100 mL) was added. Subsequently, a solution of dimethyl sulfoxide (DMSO, 6.65 g, 85.11 mmol, 2.20 eq.) in DCM (15 mL) was added dropwise and the reaction system was kept at -78 °C. At this temperature, a solution of (2-chloro-3-nitrophenyl)methanol (7.23 g, 38.54 mmol, 1.00 eq.) in DCM (35 mL) was slowly added and stirred continuously for 1 hour. Then, triethylamine (TEA, 30 mL) was added at the same temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched with water and extracted with DCM (3 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether (PE):ethyl acetate (EA) = 10:1 as eluent to afford 2-chloro-3-nitrobenzaldehyde (5.3 g, 74% yield) as a light yellow solid.

References

[1] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 936 - 944
[2] Patent: US2011/34450, 2011, A1. Location in patent: Page/Page column 101; 102
[3] Patent: US2003/225053, 2003, A1. Location in patent: Page 24
[4] Patent: US8080566, 2011, B1. Location in patent: Page/Page column 72
[5] Tetrahedron, 2000, vol. 56, # 2, p. 165 - 173

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