4,5-DICHLORO-2-NITROTOLUENE

4,5-DICHLORO-2-NITROTOLUENE Property

Melting point:

62 °C

Boiling point:

277.1±35.0 °C(Predicted)

Density 

1.456±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow to Green

InChI

InChI=1S/C7H5Cl2NO2/c1-4-2-5(8)6(9)3-7(4)10(11)12/h2-3H,1H3

InChIKey

AOTWCYSQDSKAQT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

7494-45-3

Safety

HS Code 

2904.99.4700

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.

P304IF INHALED:

P305IF IN EYES:

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P313Get medical advice/attention.

P332IF SKIN irritation occurs:

P337If eye irritation persists:

P338Remove contact lenses, if present and easy to do. Continue rinsing.

P340Remove victim to fresh air and keep at rest in a position comfortable for breathing.

P351Rinse cautiously with water for several minutes.

P352Wash with plenty of soap and water.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

4,5-DICHLORO-2-NITROTOLUENE Chemical Properties,Usage,Production

Uses

3,4-Dichloro-6-nitrotoluene is used as a reagent in the synthesis of N-hydroxyindole-2-carboxylates as inhibitors of lactate dehydrogenase against cancer cell proliferation. 3,4-Dichloro-6-nitrotoluene is also used in the preparation of polyhalogenated quinoline C-nucleosides as potential antiviral agents.This compound is suitable for lactate dehydrogenase (LDH) related research.

Synthesis

General procedure for the synthesis of 4,5-dichloro-2-nitrotoluene from 3,4-dichlorotoluene: Fuming nitric acid (40 mL) was slowly added dropwise to a solution of 1,2-dichloro-4-methylbenzene (20 g, 124.20 mmol) at 0 °C. After the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Subsequently, the reaction mixture was slowly poured into 200 mL of a water/ice mixture. The precipitated solid was collected by filtration and dried under vacuum to afford 1,2-dichloro-4-methyl-5-nitrobenzene (25.2 g, 98% yield) as a yellow solid.1H-NMR (DMSO-d6, 300 MHz) δ (ppm): 8.39 (s, 1H), 7.96 (s, 1H), 2.48 (s, 3H).

References

[1] Patent: WO2018/75959, 2018, A1. Location in patent: Paragraph 0639-0640
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1568 - 1573
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1966 - 1982
[4] Tetrahedron, 1998, vol. 54, # 12, p. 2953 - 2966
[5] Journal of the Chemical Society, 1902, vol. 81, p. 1349