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2,4-DINITROBENZENESULFENYL CHLORIDE

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2,4-DINITROBENZENESULFENYL CHLORIDE Basic information

Product Name:
2,4-DINITROBENZENESULFENYL CHLORIDE
Synonyms:
  • 2,4-dinitro-benzenesulfenylchlorid
  • KHARASCH REAGENT
  • LABOTEST-BB LT00453936
  • DNP-SULFENYL CHLORIDE
  • 2,4-Dinitrobenzenesulphenyl chloride
  • Benzenesulfenyl chloride,2,4-dinitro-
  • 2 4-DINITROPHENYL SULFENYL CHLORIDE 96%
  • 2,4-DINITROBENZENESULFENYL CHLORIDE
CAS:
528-76-7
MF:
C6H3ClN2O4S
MW:
234.62
EINECS:
208-441-2
Product Categories:
  • Biochemistry
  • Peptide Synthesis
  • Protection & Derivatization Reagents (for Synthesis)
  • Protective Reagents (Peptide Synthesis)
  • Synthetic Organic Chemistry
Mol File:
528-76-7.mol
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2,4-DINITROBENZENESULFENYL CHLORIDE Chemical Properties

Melting point:
94-97 °C(lit.)
Boiling point:
430.1±35.0 °C(Predicted)
Density 
1.700 (estimate)
refractive index 
1.6000 (estimate)
storage temp. 
2-8°C
solubility 
benzene: soluble
form 
solid
color 
Light orange to Yellow to Green
Merck 
14,3274
BRN 
405600
CAS DataBase Reference
528-76-7(CAS DataBase Reference)
EPA Substance Registry System
Benzenesulfenyl chloride, 2,4-dinitro- (528-76-7)
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Safety Information

Hazard Codes 
C
Risk Statements 
34-37
Safety Statements 
26-36/37/39-45
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
8-9-19-21
HS Code 
2930.90.2900
HazardClass 
8
PackingGroup 
III

MSDS

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2,4-DINITROBENZENESULFENYL CHLORIDE Usage And Synthesis

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 1-1½-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.

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.]

2,4-DINITROBENZENESULFENYL CHLORIDESupplier

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