7669-54-7

Usage

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.]

InChI:InChI=1/C6H4ClNO2S/c7-11-6-4-2-1-3-5(6)8(9)10/h1-4H

Upstream product

• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 33224-04-3 N-methyl-N-phenyl-2-nitrobenzenesulfenanilide 
• 541-41-3 chloroformic acid ethyl ester 
• 78945-08-1 2-nitro-benzenesulfenic acid-[1]naphthylamide 
• 98-88-4 benzoyl chloride 
• 112-67-4 n-hexadecanoyl chloride 
• 7647-01-0 hydrogenchloride 
• 4837-33-6 o-nitrobenzenesulfenanilide 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 88-73-3 2-Chloronitrobenzene 
• 22057-44-9 1-(benzylsulfanyl)-2-nitrobenzene 
• 14933-91-6 N-phenyl-benzenesulphenamide 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 89639-95-2 2-nitrophenyl chloromethyl sulfide 
• 7257-62-7 4-[(2-nitrophenyl)sulfanyl]morpholine 
• 115247-53-5 2-nitro-benzenesulfenic acid pyrimidin-2-ylamide 
• 95174-23-5 4,5-dimethyl-2-(2-nitro-phenyldisulfanyl)-thiazole 
• 14756-41-3 2-(2-nitro-phenyldisulfanyl)-benzothiazole 
• 61639-74-5 N-2-nitrophenylsulfenylphthalimide 
• 92463-14-4 o-nitrophenyl phenylselenyl sulfide 
• 39853-75-3 2-<(2-Nitrophenyl)thio>-1-cyclohexanon 
• 861072-66-4 2,4-bis-(2-nitro-phenylsulfanyl)-[1]naphthylamine 
• 33224-41-8 2-nitro-benzenesulfenic acid-(2,4-dichloro-anilide) 
• 101258-04-2 S-methyl-N-(2-nitro-benzenesulfenyl)-isothiourea 
• 100621-38-3 S-methyl-N,N'-bis-(2-nitro-benzenesulfenyl)-isothiourea 
• 102024-80-6 S-methyl-N,N,N'-tris-(2-nitro-benzenesulfenyl)-isothiourea 
• 4837-32-5 S-(2-nitrophenyl)-N-(p-tolyl)thiohydroxylamine 

Relevant academic research and scientific papers

Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents

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.

Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase

46 Novel nonsymmetrical aromatic disulfides containing [1,3,4]thiadiazole or [1,3,4]oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500 g/ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition.

An efficient preparative route to substituted alkyl benzenesulfenates, versatile reagents for site-selective sulfenylative cyclizations

A versatile procedure for the synthesis of alkyl benzenesulfenates possessing varied patterns of nuclear substitution is described.

Synthesis of Sequential Polydepsipeptides Involving Depsipeptide Formation by the 2-Nitrophenylsulphenyl N-Carboxy α-Amino Acid Anhydride (Nps-NCA) Method

Sequential polydepsipeptides containing a tripeptide sequence Ala-Ala-Glu(OEt) and various α-hydroxy acids have been successfully prepared by polycondensation of tetradepsipeptide pentachlorophenyl esters.The latter were synthesized by preparation of didepsipeptide free acids by the Nps-NCA method followed by active esterification and peptide chain elongation by the so-called 'back-up' procedure.

Sulphur-substituted Organotin Compounds. Part 8. Preparation and Reactions of 3-(p-Tolylthio)propyl- and 4-(p-Tolylthio)butyl-triphenyltin. Interactions with Tetracyanoethylene

The reactions of SnPh3 (n= 3 or 4) with mercury(II) chloride, bromine and iodine lead to phenyl-tin bond cleavage.In contrast, reactions with methyl iodide provide SnPh3 and MeSC6H4Me-p.Charge-transfer adducts are formed between SnPh3 (n= 1-4) and tetracyanoethylene or p-bromoanil.The values of λmax. of the complexes indicate similar donor character for SnPh3 (n= 2,3, or 4); however, the compound SnPh3(CH2SC6H4Me-p) is a stronger donor.