2-Chloro-5-nitrobenzonitrile Chemical Properties

Melting point:

105-107 °C (lit.)

Boiling point:

122 °C / 0.6mmHg

Density 

1.6133 (rough estimate)

refractive index 

1.5557 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

BRN 

1818642

InChI

InChI=1S/C7H3ClN2O2/c8-7-2-1-6(10(11)12)3-5(7)4-9/h1-3H

InChIKey

ZGILLTVEEBNDOB-UHFFFAOYSA-N

SMILES

C(#N)C1=CC([N+]([O-])=O)=CC=C1Cl

CAS DataBase Reference

16588-02-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-36

RIDADR 

3276

WGK Germany 

3

RTECS 

DI3040000

HazardClass 

IRRITANT

HS Code 

29269090

MSDS

• Language:English Provider:2-Chloro-5-nitrobenzonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-5-nitrobenzonitrile Usage And Synthesis

Chemical Properties

LIGHT YELLOW CRYSTALLINE POWDER. 2-Chloro-5-nitrobenzonitrile [16588-02-6], 1-chloro-2-cyano-4-nitrobenzene, Mr 182.57, mp 108 – 109℃, forms yellow needle-shaped crystals. The chlorine atom ortho to the nitrile group is prone to a range of nucleophilic substitution reactions, of which that with ammonia has achieved industrial importance. The nitrile is produced by nitration of 2-chlorobenzonitrile (see above) at 0 ℃.

Uses

2-Chloro-5-nitrobenzonitrile was used in online detection of rat glutathione S-transferase P1-specific inhibitors by high-resolution screening technology.

General Description

2-Chloro-5-nitrobenzonitrile effectively conjugates with rat glutathione S-transferase (GST) isoenzymes and is an alternative model substrate in GST-research.

Synthesis

In one embodiment of the present invention, a medium concentration of sulfuric acid solution and a medium concentration of nitric acid solution are accurately metered in proportion to each other in an acid mixing kettle. After mixing, the mixed acid is transferred to the metering tank and supplemented with an appropriate amount of nitric acid to ensure the required acidity for the reaction. Subsequently, the reaction was initiated by slowly adding 654 kg of o-chlorobenzonitrile to the nitrification reactor through the metering tank. The nitrification reaction temperature was controlled between 11 °C and 60 °C, and the reaction mixture was kept stirred in this temperature range for 1 h to ensure that the reaction proceeded adequately. The reaction process is shown in Figure 1. The specific feed amounts of the raw materials and their quality standards are detailed in Table 2. 30 kg of sulfuric acid at a concentration of 90% and 30 kg of nitric acid at a concentration of 90% were used as catalysts in the reaction system, and the amount of phthalonitrile fed was 564 kg. The composition of the reaction products was analyzed in Table 3, in which the content of 2-chloro-5-nitrobenzonitrile was 97.95%, the content of hexanitrobenzene was 1.28%, and the content of benzonitrile was 0.17%.

References

[1] Patent: CN105859581, 2016, A. Location in patent: Paragraph 4; 5

2-Chloro-5-nitrobenzonitrile(16588-02-6)Related Product Information

• 2-Chloro-5-nitrophenol
• 1-Chloro-3-nitrobenzene
• 4-Nitrobenzonitrile
• Benzonitrile
• 2-Chloro-5-nitrobenzoic acid
• 2-Chlorobenzonitrile
• 2-CHLORO-4-NITROBENZONITRILE
• 4-CHLORO-2-NITROBENZONITRILE
• 2-AMINO-3-CHLORO-5-NITROBENZONITRILE
• 2-CHLORO-5-NITROBENZONITRILE
• Difluorochloromethane
• 2,6-DICHLORO-3-NITROBENZONITRILE
• 4-Chloronitrobenzene
• 3-CHLORO-5-NITROBENZONITRILE,3-Chloro-5-nitrobenzonitrile 98%
• 4-Chloro-3-nitrobenzonitrile
• 2-CHLORO-6-NITROBENZONITRILE,6-CHLORO-2-NITROBENZONITRILE
• 5-CHLORO-2-NITROBENZONITRILE 97%,3-Chloro-6-nitrobenzonitrile,5-CHLORO-2-NITROBENZONITRILE
• 4-Chloro-2-nitroaniline