3,4,5-Trichloronitrobenzene Chemical Properties

Melting point:

68-71 °C (lit.)

Boiling point:

288°C (rough estimate)

Density 

1.8070

refractive index 

1.6300 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Orange

Water Solubility 

<0.1 g/100 mL at 15 ºC

BRN 

2505480

InChI

InChI=1S/C6H2Cl3NO2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H

InChIKey

HHLCSFGOTLUREE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20098-48-0(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,2,3-trichloro-5-nitro-(20098-48-0)

EPA Substance Registry System

Benzene, 1,2,3-trichloro-5-nitro- (20098-48-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37/39-36/37

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049090

MSDS

• Language:English Provider:1,2,3-Trichloro-5-nitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4,5-Trichloronitrobenzene Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3,4,5-Trichloronitrobenzene a reagent, used in the synthesis of INT131, a PPARγ molecule that regulates insulin sensitivity. Also is used in the synthesis of thyroid hormone receptor β selective ligands that are used in hormone treatments.

General Description

Pale-yellow crystals or yellow crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

This type of compound is incompatible with strong bases and strong oxidizing agents. .

Fire Hazard

Flash point data for 3,4,5-Trichloronitrobenzene are not available; however, 3,4,5-Trichloronitrobenzene is probably combustible.

Synthesis

General procedure for the synthesis of 1,2,3-trichloro-5-nitrobenzene from 2,6-dichloro-4-nitroaniline: 96 g of 98% concentrated sulphuric acid was added to the reaction flask at 20 °C, 7.2 g of sodium nitrite was added slowly with stirring, and then the temperature was raised to 70 °C. After the sodium nitrite was completely dissolved, the solution was cooled to 50°C. 20g of 2,6-dichloro-4-nitroaniline was added at once and the reaction was maintained at this temperature for 1 hour. After the reaction was completed, the mixture was cooled to 5 °C and 27.3 g of glacial acetic acid was slowly added dropwise. After the dropwise addition was completed, stirring was continued for 1 hour to obtain a 2,6-dichloro-4-nitroaniline diazonium salt solution. In another reaction flask, 18 g of cuprous chloride and 7.14 g of concentrated hydrochloric acid were added. The above diazonium salt solution was slowly added dropwise to this reaction flask under rapid stirring, keeping the temperature below 15 °C. After completion of the dropwise addition, the reaction was maintained for 1 hour, followed by raising the temperature to 70°C to continue the reaction for 1 hour. At the end of the reaction, the mixture was cooled to room temperature, poured into a 2L reaction flask, and 60 g of water was added under stirring. 0.5 h later, filtration was carried out to obtain 1,2,3-trichloro-5-nitrobenzene as a yellow solid with a dry weight of 21.5 g. The yield was 98.5%, and the purity was 98.3% by HPLC.

References

[1] Patent: CN104447597, 2018, B. Location in patent: Paragraph 0020; 0023; 0045-0047
[2] Patent: CN107746390, 2018, A. Location in patent: Paragraph 0021; 0022; 0023
[3] Journal of Medicinal Chemistry, 1980, vol. 23, # 10, p. 1083 - 1087
[4] Journal of the Chemical Society, 1926, p. 3044
[5] Patent: CN104098521, 2016, B. Location in patent: Paragraph 0038; 0039; 0040; 0041

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