5-Chloro-2-nitrobenzoic acid Chemical Properties

Melting point:

137-139 °C (lit.)

Boiling point:

160.5°C (rough estimate)

Density 

1,608g/cm

refractive index 

1.6000 (estimate)

Flash point:

100 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

9.67g/l

pka

1.86±0.25(Predicted)

form 

Crystalline Powder

color 

Light yellow to yellow-green

Water Solubility 

SLIGHTLY SOLUBLE

BRN 

1963952

InChIKey

ZKUYSJHXBFFGPU-UHFFFAOYSA-N

CAS DataBase Reference

2516-95-2(CAS DataBase Reference)

NIST Chemistry Reference

5-Chloro-2-nitrobenzoic acid(2516-95-2)

EPA Substance Registry System

Benzoic acid, 5-chloro-2-nitro- (2516-95-2)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-50/53-41-37/38-22

Safety Statements 

22-24/25-61-60-36/37/39-26-36

RIDADR 

UN3077 9/PG 3

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

9

PackingGroup 

Ⅲ

HS Code 

29163900

MSDS

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5-Chloro-2-nitrobenzoic acid Usage And Synthesis

Chemical Properties

light yellow to yellowish-green crystalline powder.
5-Chloro-2-nitrobenzoic acid is a crystalline solid sparingly soluble in cold water but readily soluble in hot water and also in ethanol and benzene. Its electrolytic dissociation constant is 1.52 × 10?2 (25 °C), and its melting point is 139 °C.

Uses

5-Chloro-2-nitrobenzoic acid was used as a component of 5,5′-dithiobis-2-nitrobenzoic acid, which found application to the determination of the acid-soluble disulphide content of the blood. Benzene and some of its derivatives (e.g. chloronitrobenzoic acids) have been shown to cause alterations in heme and globin synthesis. Chloronitrobenzoic acids inhibited the activity of δ-aminolevulinic acid (δ-ALA) and enhanced ferrochelatase (FC) activity. 5-Chloro-2-nitrobenzoic acid was also used as component of synthesis of 2-aryl 4(3H)-quinazolinones and 6-pyrrolidinyl-2-(2-substituted phenyl)-4-quinazolinones, which are potential anticancer candidates[1].

Synthesis

Fe(NO3)3-9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol) and 5-chloro-2-nitrobenzenemethanol (108.5 mg, 1.0 mmol) were added sequentially to the Schlenk tube. Under oxygen atmosphere, DCE (4.0 mL) was added (using a gas bag, commercial size: 2 L, expandable to 5 L). The reaction mixture was stirred at 25 °C and the progress of the reaction was monitored by TLC (unfolding agent: petroleum ether/EtOAc = 5:1) until the reaction was complete (~48 h). After completion of the reaction, the crude reaction mixture was filtered through a short silica gel column (height: 2 cm, diameter: 3 cm) and eluted with Et2O (3 × 25 mL). After evaporation of the solvent, the residue was purified by silica gel column chromatography [eluent: petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford 5-chloro-2-nitrobenzoic acid (69.9 mg, 57% yield) as a pale yellow solid. The yield of 5-chloro-2-nitrobenzoic acid in the crude product was determined to be 57% by NMR analysis, using CH2Br2 as an internal standard and comparing the spectral data with those reported in the literature, while 5-chloro-2-nitrobenzaldehyde was detected in 38% yield.

References

[1] W. Ferenc, J. Sarzyński, B. Cristóv?o. “Thermal and magnetic behaviour of 5-chloro-2-nitrobenzoates of Co(II), Ni(II) and Cu(II).” Journal of Thermal Analysis and Calorimetry 34 1 (2010): 761–767.

5-Chloro-2-nitrobenzoic acid(2516-95-2)Related Product Information

• 5-Chloro-2-methylbenzoic acid
• 3-Nitrobenzoic acid
• Epichlorohydrin
• 2-Nitrobenzoic acid
• 4-Nitrobenzoic acid
• 2-Chlorobenzoic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Chloro-3-nitrobenzoic acid
• 1-Chloro-3-nitrobenzene
• NITROGEN DIOXIDE
• Methyl chloroformate
• 4-Chloronitrobenzene
• 2-Nitrochlorobenzene
• Difluorochloromethane
• Chloroacetic acid
• Ethyl chloroformate
• 5-CHLORO-2-NITROBENZOIC ACID METHYL ESTER,METHYL 5-CHLORO-2-NITROBENZOIC ACID
• 5-CHLORO-2,4-DINITROBENZOIC ACID