| Identification | More | [Name]
2,4-DINITROBENZENESULFENYL CHLORIDE | [CAS]
528-76-7 | [Synonyms]
2,4-DINITROBENZENESULFENYL CHLORIDE
2,4-DINITROPHENYLSULFENYL CHLORIDE
DNP-SULFENYL CHLORIDE
KHARASCH REAGENT
LABOTEST-BB LT00453936
2,4-dinitro-benzenesulfenylchlorid
2,4-Dinitrobenzenesulphenyl chloride
Benzenesulfenyl chloride,2,4-dinitro-
2 4-DINITROPHENYL SULFENYL CHLORIDE 96%
2,4-Dinitrophenylsulfenyl chloride, Kharasch reagent
(2,4-Dinitrophenylthio) chloride
2,4-Dinitrophenylthio chloride | [EINECS(EC#)]
208-441-2 | [Molecular Formula]
C6H3ClN2O4S | [MDL Number]
MFCD00007129 | [Molecular Weight]
234.62 | [MOL File]
528-76-7.mol |
| Questions And Answer(Q&A) | Back Directory | [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 1-1½-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 ½ 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.
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| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
8-9-19-21 | [HS Code ]
2930.90.2900 | [HazardClass ]
8 | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Uses]
2,4-Dinitrobenzenesulfenyl chloride was used in preparation of chlorine and bromine biphenyls. | [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.] |
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| Company Name: |
Energy Chemical
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021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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