5-Chloro-2-nitrotoluene Chemical Properties

Melting point:

27-30 °C (lit.)

Boiling point:

124-126 °C (16 mmHg)

Density 

1.32

refractive index 

1.57-1.572

Flash point:

202 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to lump

color 

White to Light yellow

Water Solubility 

insoluble

CAS DataBase Reference

5367-28-2(CAS DataBase Reference)

NIST Chemistry Reference

5-Chloro-2-nitrotoluene(5367-28-2)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36-36/37/38-20/21/22-52/53

Safety Statements 

26-36-36/37/39-61

RIDADR 

UN 3457 6.1/PG 3

WGK Germany 

3

RTECS 

XS9134000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049090

MSDS

• Language:English Provider:3-Chloro-6-nitrotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Chloro-2-nitrotoluene Usage And Synthesis

Application

5-Chloro-2-nitrotoluene is an organic intermediate that can be obtained by nitrifying o-chlorotoluene.

Chemical Properties

clear yellow liquid

General Description

The cytotoxicity of 5-chloro-2-nitrotoluene, an analog of chlorphenamidine, was studied.

Synthesis

General procedure for the synthesis of 5-chloro-2-nitrotoluene and 3-chloro-4-nitrotoluene from 3-chlorotoluene: Concentrated nitric acid (16 mL) was added slowly and dropwise at 0°C to a solution of glacial acetic acid (20 mL) containing 3-chlorotoluene (3 mL, 25.4 mmol) and concentrated sulfuric acid (6 mL). The reaction mixture was stirred at room temperature for 24 hours. Subsequently, the reaction mixture was poured into ice water and liquid-liquid partitioned with ether. After separating the aqueous phase, the aqueous phase was extracted twice with ether. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The yellow oily crude product obtained was purified by silica gel column chromatography and after two rapid chromatographic separations, 1.22 g (14% yield) of 5-chloro-2-nitrotoluene (yellow oily) and 3.39 g (39% yield) of 3-chloro-4-nitrotoluene were obtained.

References

[1] Patent: US2012/15962, 2012, A1. Location in patent: Page/Page column 83
[2] Chemische Berichte, 1900, vol. 33, p. 2505
[3] Bulletin de la Societe Chimique de France, 1900, vol. <3> 23, p. 838
[4] Chemische Berichte, 1900, vol. 33, p. 2505,2506

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