528-76-7

Usage

Uses

Used in Chemical Synthesis:
2,4-Dinitrobenzenesulfenyl chloride is used as a reagent in the preparation of chlorine and bromine biphenyls. Its unique chemical properties allow it to facilitate the formation of these complex organic compounds, which have various applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-dinitrobenzenesulfenyl chloride is used as a synthetic intermediate for the production of various drugs and pharmaceutical compounds. Its ability to participate in addition reactions and convert allylic alcohols to dienes makes it a valuable tool in the synthesis of complex molecular structures.
Used in Research and Development:
2,4-Dinitrobenzenesulfenyl chloride is also utilized in research and development settings, where its reactivity and versatility in chemical reactions are harnessed to explore new synthetic pathways and develop novel compounds with potential applications in various fields, including materials science, agriculture, and environmental science.

Preparation

CAUTION: This reaction should be carried out in a hood behind a safety shield. The product decomposes explosively if heated above 90-100°C . To a 500-ml, three-necked flask equipped with a mechanical stirrer, distillation column, and distillation head is added 100 gm (0.25 mole) of dry 2,4-dinitrophenyl disulfide and 250 ml of ethylene chloride. The contents are heated with an oil bath at 125°C until 30-40 ml of the solvent is collected by distillation. The contents are cooled and the distillation head replaced by a gas inlet and exit tube connected to an alkali trap. Then 0.15 gm (0.002 mole) of Merck "Iron by Hydrogen" powder is added as a catalyst [51a-c], and dry chlorine gas is slowly bubbled into the reaction. In a few minutes, the reaction warms up, and the flask is surrounded with a 20°C water bath. The chlorine gas is bubbled in at such a rate that 18 gm (0.25 mole) is added over a 1-1?-hr period. After this time, the suspended disulfide should gradually disappear, and a clear, amber-red solution results. The flow of chlorine gas is stopped, the solution stirred for 1 hr, filtered through diatomaceous earth, the filtrate aspirated to remove excess chlorine, and then 400 ml of anhydrous ether is added. Within ? hr, most of the product crystallizes by cooling the flask in an ice-salt-water bath for 3-4 hr. The product is filtered, washed with 100 ml of cold ether, and then dried to afford 70 gm (60%) of brilliant yellow needles, m.p. 95-95.5°C.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1796, 1950 DOI: 10.1021/ja01160a108

Purification Methods

Crystallise the sulfenyl chloride from CCl4. [Beilstein 6 II 316.]

InChI:InChI=1/C6H3ClN2O4S/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H

Upstream product

• 128-09-6 N-chloro-succinimide 
• 2218-96-4 2,4-dinitrothiophenol 
• 35539-24-3 S-2,4-dinitrophenyl thiobenzoate 
• 60775-11-3 1-benzyl-2-(2,4-dinitrophenyl)disulfane 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 7343-61-5 benzyl-(2,4-dinitro-phenyl)-sulfide 
• 2217-55-2 bis(2,4-dinitrophenyl) disulphide 

Downstream Products

• 32894-59-0 N-(2,4-Dinitrobenzol-sulfenyl)-piperidin 
• 22552-36-9 2-(2,4-dinitro-phenylsulfanyl)-thiophene 
• 109557-05-3 4-chloro-1-(2,6-dichloro-benzyl)-5-(2,4-dinitro-phenylsulfanyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid amide 
• 100119-26-4 (+/-)-2,4-dinitro-benzenesulfenic acid-(trans-2-chloro-cyclohexyl ester) 
• 21851-47-8 2-(2,4-dinitrophenylthio)-1-phenyl-1-chloroethane 
• 10344-04-4 dinitrobenzenesulfenic acid methyl ester 
• 10344-07-7 2,4-dinitro-benzenesulfenic acid propyl ester 
• 73959-94-1 (E)-β-(2,4-dinitro-phenylsulfanyl)-4-methoxy-styrene 
• 61807-32-7 (2,4-dinitro-phenyl)-(2,2-diphenyl-vinyl)-sulfide 
• 2218-96-4 2,4-dinitrothiophenol 
• 60775-11-3 1-benzyl-2-(2,4-dinitrophenyl)disulfane 
• 89039-18-9 (β-chloro-4-methyl-phenethyl)-(2,4-dinitro-phenyl)-sulfide 
• 99361-70-3 trans-1-acetoxy-2-(2,4-dinitro-phenylsulfanyl)-ethene 
• 60775-10-2 (4-bromo-phenyl)-(2,4-dinitro-phenyl)-sulfide 

Relevant academic research and scientific papers

Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents

A total of 29 novel sulfenamide compounds were synthesized, spectroscopically characterized and evaluated in vitro for antimicrobial activity against various infectious pathogens. Compounds 1b and 2c exhibited potent inhibition against clinical Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentration (MIC) values of 1.56 μg/mL.

Electrophilic cleavage of cyclopropanes. II. Concerning the effect of increasing electron demand upon the product-determining transition state in the reaction of 4-substituted-2-nitrobenzenesulphenyl chlorides and benzenesulphenyl chlorides with tetracyclo2,7.04,6>heptane....

The effect of increasing electron demand upon the product-determining transition state in the reaction of arenesulphenyl chlorides with tetracyclo2,7.04,6>heptane has been investigated.As the electron donating ability of the remote substituents on the phenyl ring of the sulphenyl chloride is varied from nitro to methoxy the relative proportion of adducts derived from edge-on attack is found to increase relative to that of adducts derived from corner attack.An ortho-nitro group was found to lead to a stabilizing interaction only in the case of 2,4-dinitrobenzenesulphenyl chloride.A mechanism involving the competition between the two conceptual modes of approach is suggested.