| Identification | Back Directory | [Name]
4,5-DICHLORO-2-NITROTOLUENE | [CAS]
7494-45-3 | [Synonyms]
7494-45-3
4,5-DICHLORO-2-NITROTOLUENE
4,5-Dichloro-2-nitrotoluene>
4,5-Dichloro-2-Methylnitrobenzene
1,2-DICHLORO-4-METHYL-5-NITRO-BENZENE
Benzene, 1,2-dichloro-4-methyl-5-nitro- | [Molecular Formula]
C7H5Cl2NO2 | [MDL Number]
MFCD01109847 | [MOL File]
7494-45-3.mol | [Molecular Weight]
206.03 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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