2-Nitrobenzenesulfenyl chloride

2-Nitrobenzenesulfenyl chloride Basic information
Product Name:2-Nitrobenzenesulfenyl chloride
Synonyms:2-NITROBENZENESULPHENYL CHLORIDE;2-NITROPHENYLSULFENYL CHLORIDE;2-NITROBENZENESULFENYL CHLORIDE;NPS REAGENT;NPS-CL;o-nitrobenzenesulphenyl chloride;O-NITROBENZENESULFENYL CHLORIDE;O-NITROPHENYLSULFENYL CHLORIDE
CAS:7669-54-7
MF:C6H4ClNO2S
MW:189.62
EINECS:231-644-2
Product Categories:Biochemistry;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry
Mol File:7669-54-7.mol
2-Nitrobenzenesulfenyl chloride Structure
2-Nitrobenzenesulfenyl chloride Chemical Properties
Melting point 70-75 °C
Boiling point 350.0±25.0 °C(Predicted)
density 1.492 (estimate)
refractive index 1.6000 (estimate)
storage temp. 2-8°C
form Crystalline Powder or Needles
color Yellow to gold
Water Solubility decomposes
Sensitive Moisture Sensitive
BRN 473741
CAS DataBase Reference7669-54-7(CAS DataBase Reference)
EPA Substance Registry SystemBenzenesulfenyl chloride, 2-nitro- (7669-54-7)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 36/39-45-36/37/39-26
RIDADR 3261
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29309090
MSDS Information
ProviderLanguage
2-Nitrophenylsulfenyl chloride English
ACROS English
ALFA English
2-Nitrobenzenesulfenyl chloride Usage And Synthesis
Chemical Propertiesyellow to gold crystalline powder or needles
Uses2-Nitrobenzenesulfenyl Chloride is used in the synthesis of α-amino phosphonic acids
PreparationCAUTION: This chloride is explosive, and the solvent has to be removed under reduced pressure.
To a 500-ml, three-necked flask equipped with a mechanical stirrer, thermometer, gas addition tube, and condenser is added 200 ml of dry carbon tetrachloride, 30 gm (0.1 mole) of 2,2'-dinitrophenyl disulfide, and 0.05 gm of iodine as a catalyst. The suspension is heated to 50-60°C, and chlorine gas is added at such a flow rate that 10 gm (0.14 mole) is added over a 2-2^-hr period at this temperature. After this time, the solid starting disulfide finally goes into solution, and the warm dark yellow solution is filtered. The solution is cooled to 5°C, and the product that crystallizes out is filtered and dried to afford 25.2-27.0 gm (66-71%), m.p. 73-74.5°C.
Preparation of 2-Nitrobenzenesulfenyl Chloride

Purification MethodsRecrystallise it from CCl4 (2mL/g), filter off the solution at 5o (recovery 75%). It has also been recrystallised from pet ether (b 40-60o), dried rapidly at 50o and stored in a brown glass bottle, sealed well and stored away from moisture. [Hubacher Org Synth Coll Vol II 455 1943, Ito et al. Chem Pharm Bull Jpn 26 296 1978, Beilstein 6 I 157.]
2-Nitrobenzenesulfenyl chloride Preparation Products And Raw materials
Raw materialsCarbon tetrachloride-->1,3-Dinitrobenzene
Preparation Products2-NITROTHIOPHENOL-->N-METHYL-N-PHENYLURETHANE-->N-(2-NITROPHENYLTHIO)SACCHARIN, 95%
2-Nitrobenzenesulfonyl chloride 2,4-DINITROBENZENESULFONYL CHLORIDE Benzyl chloride alpha-Chloro-o-fluorotoluene Calcium chloride 2-Nitrochlorobenzene Sodium chloride 2-NITRO-4-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE 4-METHYL-2-NITROBENZENESULFONYL CHLORIDE 2-NITRO-4-CARBOXYPHENYLSULFENYL CHLORIDE 2-Methylbenzyl chloride Ammonium chloride Nitrobenzene Polyvinyl chloride 2-Chloroaniline 2,4-DINITROBENZENESULFENYL CHLORIDE Potassium chloride 4-METHOXY-2-NITROBENZENESULFONYL CHLORIDE

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