28286-86-4

Basic information

• Product Name: 2,4-DICHLORO-5-METHYLBENZENESULFONYL CHLORIDE
• Synonyms: 4,6-DICHLORO-M-TOLUENESULFONYL CHLORIDE;2,4-DICHLORO-5-METHYLBENZENE-1-SULFONYL CHLORIDE;2,4-DICHLORO-5-METHYLBENZENESULFONYL CHLORIDE;2,4-dichloro-5-methylbenzene-1-sulphonyl chloride;2,4-Dichloro-5-methylbenzenesulphonyl chloride;2,4-Dichloro-5-methylbenzenesulfonic acid chloride;2,4-Dichloro-5-methylbenzenesulfonyl chloride,97%;2,4-Dichloro-5-methylbenzene-1-sulfonyl chloride, 95%+
• CAS NO: 28286-86-4
• Molecular Formula: C₇H₅Cl₃O₂S
• Molecular Weight: 259.54
• EINECS: 248-938-1
• Mol File: 28286-86-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 67-72 °C
• Boiling Point: 333.2°Cat760mmHg
• Flash Point: 155.3°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 0.000268mmHg at 25°C
• Refractive Index: 1.571
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2,4-DICHLORO-5-METHYLBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-5-METHYLBENZENESULFONYL CHLORIDE(28286-86-4)
• EPA Substance Registry System: 2,4-DICHLORO-5-METHYLBENZENESULFONYL CHLORIDE(28286-86-4)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36
• Safety Statements: 45-36/37/39-26
• RIDADR: 1760
• RTECS: QR8650000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 28286-86-4(Hazardous Substances Data)

Usage

Chemical Properties

off-white crystalline powder

InChI:InChI=1/C7H5Cl3O2S/c1-4-2-7(13(10,11)12)6(9)3-5(4)8/h2-3H,1H3

Upstream product

• 95-73-8 2,4-dichlorotoluene 

Downstream Products

• 925442-27-9 2,4-dichloro-N-(4-formyl-3,5-dimethylphenyl)-5-methylbenzenesulfonamide 
• 235427-10-8 C₂₁H₁₈Cl₃N₃O₄S 
• 1269500-14-2 C₂₂H₂₇Cl₂N₃O₅S 
• 1032418-30-6 N-(4-methylbenzoyl)-N'-(2,4-dichloro-5-methylphenylsulfonyl)hydrazine 
• 1032418-29-3 N-(4-chlorobenzoyl)-N'-(2,4-dichloro-5-methylphenylsulfonyl)hydrazine 
• 1136536-87-2 3-(2,4-dichloro-5-methylphenylsulfonylamino)-6-chloropyridazine 
• 295790-33-9 N-{2-[4-(1H-benzimidazol-2-yl)piperazin-1-yl]ethyl}-2,4-dichloro-5,N-dimethylbenzenesulfonamide 
• 295790-57-7 2,4-dichloro-5-methyl-N-(2-chloroethyl)-N-methylbenzenesulfonamide 
• 64454-20-2 2.4-Dichlor-5-methylphenylthioacetaldehyd-diethylacetal 

Relevant articles and documents

Redox-active dinitrodiphenylthioethers against Leishmania: Synthesis, structure-activity relationships and mechanism of action studies

BTB 06237 (2-[(2,4-dichloro-5-methylphenyl)sulfanyl]-1,3-dinitro-5-(trifluoromethyl) benzene), a compound previously identified through QSAR pharmacophore development and a virtual screen of the Maybridge database, possesses potent and selective activity against Leishmania parasites. In the present study, several analogs of BTB 06237 were synthesized and analyzed for activity against Leishmania axenic amastigotes, their ability to reduce the level of parasitemia in peritoneal macrophages, and their ability to generate reactive oxygen species (ROS) in L. donovani promastigotes. It was found that an aromatic ring must be present in the position occupied by the 2,4-dichloro-5-methylphenyl group in the lead compound, but changing the functional groups generally has little effect on the antileishmanial potency. Alterations to the 1,3-dinitro-5-(trifluoromethyl)benzene ring have more influence on antiparasitic activity with two aromatic nitro groups and a third electron-withdrawing group being required. This structural requirement corresponds with redox potential, the ability to generate ROS in the parasites, and dissipation of the mitochondrial membrane potential. Finally, we used this collection of data to design a new antileishmanial compound with strong activity in vitro and improved properties as an antileishmanial candidate.