2,6-DICHLORO-3-NITROBENZOIC ACID Chemical Properties

Melting point:

152-158 °C(lit.)

Boiling point:

374.4±42.0 °C(Predicted)

Density 

1.713±0.06 g/cm3(Predicted)

Flash point:

152-158°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

0.76±0.29(Predicted)

color 

White to Orange to Green

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2916399090

MSDS

• Language:English Provider:SigmaAldrich

2,6-DICHLORO-3-NITROBENZOIC ACID Usage And Synthesis

Uses

2,6-Dichloro-3-nitrobenzoic acid may be used in the preparation of 9-chloro-2-methoxy-6-nitro-5,10-dihydrobenzo[b][1,5]naphthyridin-10-one, required for the synthesis of potential DNA-binding antitumor agents. It may be used in the preparation of 2-(aminoalkyl)-5-nitropyrazolo [3,4,5-kl] acridines.

General Description

FT-IR and Raman spectra of 2, 6-dichloro-3-nitrobenzoic acid (DCNBA) have been investigated.

Synthesis

Step a: Synthesis of 2,6-dichloro-3-nitrobenzoic acid 2,6-Dichlorobenzoic acid (10 g, 52 mmol) was added to a pre-stirred mixture of nitric acid (15 mL) and sulfuric acid (30 mL) and reacted at 55 °C for 30 min, followed by continued stirring at room temperature for 30 min. Upon completion of the reaction, the reaction mixture was slowly poured into ice-cold water (1 L) and the precipitated solid was filtered and dried to afford 2,6-dichloro-3-nitrobenzoic acid (9 g). The filtrate was extracted with ethyl acetate (2 x 200 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to dryness to give the additional product (2 g). The total yield was 11 g in 88% yield. 1H NMR (400 MHz, MeOH-d4): δ 7.98 (d, J=8.8 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H).

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6597 - 6611
[2] Patent: WO2012/160464, 2012, A1. Location in patent: Page/Page column 79
[3] Patent: US2014/155398, 2014, A1. Location in patent: Paragraph 0474
[4] Chemische Berichte, 1987, vol. 120, p. 803 - 810
[5] Chemische Berichte, 1937, vol. 70, p. 1526,1531

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