3-Chloro-2-nitrobenzoic acid

3-Chloro-2-nitrobenzoic acid Property

Melting point:

237-239 °C (lit.)

Boiling point:

365.6±27.0 °C(Predicted)

Density 

1.5660

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

1.82±0.10(Predicted)

color 

White to Off-White

Water Solubility 

0.47g/L(25 ºC)

BRN 

2109828

InChI

InChI=1S/C7H4ClNO4/c8-5-3-1-2-4(7(10)11)6(5)9(12)13/h1-3H,(H,10,11)

InChIKey

VCHSXYHBMFKRBK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4771-47-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25-36

WGK Germany 

3

HazardClass 

IRRITANT-HARMFUL

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Chloro-2-nitrobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

almost white to beige crystalline powder

Uses

3-Chloro-2-nitrobenzoic acid has been used in the preparation of:

• 2-amino-3-chlorobenzonitrile
• 3-chloro-2-nitrobenzaldehyde

General Description

Hydrogen-bonded structures of isomeric compounds of 3-chloro-2-nitrobenzoic acid with quinoline have been investigated.

Synthesis

General procedure for the synthesis of 3-chloro-2-nitrobenzoic acid from 2-amino-3-chlorobenzoic acid: 216 g of glacial acetic acid was added to a 500 ml triple-necked flask, a condensing unit was installed and stirring was turned on. Subsequently, 57 g of sodium borate and 5 g of titanate catalyst prepared in Example 1 were added. The internal air of the system was replaced with nitrogen three times and the reaction temperature was raised to 85°C. Under stirring conditions, a mixed solution comprising 10 g of 2-amino-3-chlorobenzoic acid and 30 g of glacial acetic acid was slowly added dropwise. The reaction temperature was maintained at 85°C-90°C and the reaction was stirred for 1 hour. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the system was cooled to room temperature and the reaction mixture was filtered. The resulting solid was washed with 20 g of methanol and subsequently dried under vacuum at 40°C -50°C for 3 h to give 11.3 g of 2-nitro-3-chlorobenzoic acid crude product. 40 g of the crude product was dissolved in anhydrous ethanol, 2-nitro-3-chlorobenzoic acid was added and heated to 75°C -80°C refluxing for 0.5 hours. The temperature of the reaction solution was then lowered to 0°C -5°C, held and stirred for 0.5 hours and filtered. The solid was dried under vacuum at 40°C -50°C for 3 hours to obtain 10 g of 2-nitro-3-chlorobenzoic acid with 99.7% purity and 84.9% yield.

References

[1] Patent: CN104086429, 2016, B. Location in patent: Paragraph 0040; 0041; 0042