21272-85-5

Basic information

• Product Name: NITROMETHYL PHENYL SULFONE
• Synonyms: BENZENESULPHONYL NITROMETHANE;BENZENESULFONYLNITROMETHANE;4-BENZENESULPHONYLNITROMETHANE;TIMTEC-BB SBB003532;(NITROMETHYL)(DIOXO)PHENYL-LAMBDA6-SULFANE;NITROMETHYL PHENYL SULFONE;(NITROMETHYLSULFONYL)BENZENE;(PHENYLSULFONYL)NITROMETHANE
• CAS NO: 21272-85-5
• Molecular Formula: C₇H₇NO₄S
• Molecular Weight: 201.2
• EINECS: 244-308-5
• Mol File: 21272-85-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 78-80 °C
• Boiling Point: 399.8 °C at 760 mmHg
• Flash Point: 195.6 °C
• Appearance: /
• Density: 1.397 g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Refractive Index: 1.555
• PKA: 4.07±0.29(Predicted)
• BRN: 1876502
• CAS DataBase Reference: NITROMETHYL PHENYL SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: NITROMETHYL PHENYL SULFONE(21272-85-5)
• EPA Substance Registry System: NITROMETHYL PHENYL SULFONE(21272-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 21272-85-5(Hazardous Substances Data)

Usage

Purification Methods

Recrystallise the sulfone from CHCl3, or 95% EtOH, then sublime it at 100-120o/0.1 Torr and recrystallise again. It is an acidic analogue of nitromethane used for the general synthesis of aliphatic acids and nitriles and in cycloaddition reactions with olefins to form heterocycles. [Wade et al. J Org Chem 46 765 1981, 49 4595 1984, Beilstein 6 II 292.]

InChI:InChI=1/C7H7NO4S/c9-8(10)6-13(11,12)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 1794-84-9 monochloronitromethane 
• 873-55-2 sodium benzenesulfonate 
• 75-52-5 nitromethane 
• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 77422-70-9 azidomethyl phenyl sulphide 
• 100-39-0 benzyl bromide 
• 74737-89-6 phenylsulfonylnitromethane sodium salt 
• 6940-76-7 1-iodo-3-chloro-propane 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 74738-03-7 lithium <(phenylsulfonyl)methylene>nitronate 
• 60595-16-6 (phenylthio)nitromethane 
• 64-17-5 ethanol 
• 618-41-7 Benzenesulfinic acid 

Downstream Products

• 87843-08-1 1-((3aS,4R,7aR)-3-Benzenesulfonyl-4-phenyl-3a,7a-dihydro-4H-isoxazolo[4,5-c]pyridin-5-yl)-ethanone 
• 87843-07-0 (3aR,7aS)-3-Benzenesulfonyl-3a,7a-dihydro-4H-isoxazolo[4,5-c]pyridine-5-carboxylic acid methyl ester 
• 87843-09-2 1-((3aS,4S,7aR)-3-Benzenesulfonyl-4-butyl-3a,7a-dihydro-4H-isoxazolo[4,5-c]pyridin-5-yl)-ethanone 
• 78258-04-5 1-nitro-1-(phenylsulfonyl)heptane 
• 74737-90-9 1-nitro-1-(phenylsulfonyl)ethane 
• 1141926-17-1 2,4-dinitro-2,4-bis(phenylsulfonyl)butan-1-ol 
• 1141926-23-9 2,4-dinitro-2,4-bis(phenylsulfonyl)-pentane-1,5-diol 
• 1082-18-4 C₁₆H₁₆ 
• 1589528-73-3 (E)-6-nitro-6-(phenylsulfonyl)hept-3-en-1-yl benzoate 

Relevant articles and documents

Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes

The comparative reaction efficiencies of currently used nucleophilic and electrophilic probes toward cysteine sulfenic acid have been thoroughly evaluated in two different settings-(i) a small molecule dipeptide based model and (ii) a recombinant protein model. We further evaluated the stability of corresponding thioether and sulfoxide adducts under reducing conditions which are commonly encountered during proteomic protocols and in cell analysis. Powered by the development of new cyclic and linear C-nucleophiles, the unsurpassed efficiency in the capture of sulfenic acid under competitive conditions is achieved and thus holds great promise as highly potent tools for activity-based sulfenome profiling.

A simple synthesis of some new arylsulfonylnitromethanes

Arylsulfonylnitromethanes were obtained by a nucleophilic substitution reaction. The suggested method of obtaining arylsulfonylnitromethanes has some important advantages over the methods known so far: It is a relatively short, one-stage process; no byproducts are obtained, so there is no need for further procedures to separate the main products from thereaction mixture; and the final compounds possess a good degree of purity. The structure of the new products were confirmed by 1H NMR, IR, and elemental analysis. The solid state structure of 6 was established by X-ray analysis. Copyright

Reactions of (1-nitroethenyl)sulfonylbenzene, a nitroethene derivative geminally substituted by a second W-group

Nitroaldol reaction of phenylsulfonylnitromethane with formaldehyde affords a mixture of 2, 4-dinitro-2, 4-bis (phe-nylsulfonyl)butan-1-ol and 2, 4-dinitro-2, 4- bis (phenylsulfonyl)pentane-1, 5-diol. Treatment of this mixture with base followed by reacidification affords 1,1′-[(1, 3-dinitro-1, 3-propanediyl)bis (sulfonyl)]bis (benzene) as a mixture of (R*, R*) and (R*, S*)- diastereomers from which the (R*, S*)- diastereomer can be obtained pure. The intermediate in the nitroaldol reaction is (1-nitroethenyl)sulfonylbenzene and, if dienes are present, additional products are also obtained. If either (E)-2-methyl-1, 3-pentadiene or 1-(1-methylethenyl)cyclohexene are present, typical Diels-Alder adducts are obtained with the major isomers explainable by assuming a transition state in which the nitro group is endo. If furan is present, its formal conjugate addition product, 2-[2-nitro-2-(phenylsulfonyl)ethyl]furan, is formed. If cyclooctatetraene is present, it first dimerizes and then affords isomeric Diels-Alder cycloadducts of the dimer. Semiempirical calculations comparing the LUMO energies of (1-nitroethenyl)sulfonylbenzene to the corresponding trans-1,2 isomer are presented to explain relative reactivity of 1, 1- and 1, 2-disubstituted dienophiles. Copyright