4,5-DICHLORO-2-NITROTOLUENE Chemical Properties

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 Information

HS Code 

2904.99.4700

4,5-DICHLORO-2-NITROTOLUENE Usage And Synthesis

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

4,5-DICHLORO-2-NITROTOLUENE(7494-45-3)Related Product Information

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• 2,6-DICHLORO-3-NITROTOLUENE, 99% ** SEE,2,6-DICHLORO-3-NITROTOLUENE
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• 2,5-dichloro-3-nitrotoluene-4-sulphonic acid
• 2,6-Dichloro-4-Nitrotoluene
• α,α-Dichloro-m-nitrotoluene
• 2,6-dichloro-3-nitrotoluene-4-sulphonic acid