528-76-7 Usage
Uses
2,4-Dinitrobenzenesulfenyl chloride was used in preparation of chlorine and bromine biphenyls.
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
General Description
2,4-Dinitrobenzenesulfenyl chloride undergoes addition reactions with transannularly substituted cycloalkenes and norbornenes. 2,4-Dinitrobenzenesulfenyl chloride can convert allylic alcohols to dienes by 1,4-elimination.
Purification Methods
Crystallise the sulfenyl chloride from CCl4. [Beilstein 6 II 316.]
Check Digit Verification of cas no
The CAS Registry Mumber 528-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 528-76:
(5*5)+(4*2)+(3*8)+(2*7)+(1*6)=77
77 % 10 = 7
So 528-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H3ClN2O4S/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H
528-76-7Relevant articles and documents
Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents
Shang, Jian-Li,Guo, Hui,Li, Zai-Shun,Ren, Biao,Li, Zheng-Ming,Dai, Huan-Qin,Zhang, Li-Xin,Wang, Jian-Guo
, p. 724 - 727 (2013/02/25)
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.
