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 Reference

7669-54-7(CAS DataBase Reference)

EPA Substance Registry System

Benzenesulfenyl 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

• Language:English Provider:2-Nitrophenylsulfenyl chloride
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2-Nitrobenzenesulfenyl chloride Usage And Synthesis

Chemical Properties

yellow to gold crystalline powder or needles

Uses

2-Nitrobenzenesulfenyl Chloride is used in the synthesis of α-amino phosphonic acids

Preparation

CAUTION: 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.

Purification Methods

Recrystallise 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.]

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