1142-27-4

Basic information

• Product Name: p-nitrophenyl dimethylsulphamate
• Synonyms: p-nitrophenyl dimethylsulphamate;Dimethylsulfamic acid 4-nitrophenyl ester;p-nitrophenyl dimethylsulfamate
• CAS NO: 1142-27-4
• Molecular Formula: C₈H₁₀N₂O₅S
• Molecular Weight: 246.2404
• EINECS: 214-533-3
• Mol File: 1142-27-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 377.4°Cat760mmHg
• Flash Point: 182°C
• Appearance: /
• Density: 1.447g/cm³
• Vapor Pressure: 6.78E-06mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: p-nitrophenyl dimethylsulphamate(CAS DataBase Reference)
• NIST Chemistry Reference: p-nitrophenyl dimethylsulphamate(1142-27-4)
• EPA Substance Registry System: p-nitrophenyl dimethylsulphamate(1142-27-4)

Safety Data

• Hazardous Substances Data: 1142-27-4(Hazardous Substances Data)

Usage

General Description

p-Nitrophenyl dimethylsulphamate is a chemical compound that belongs to the class of sulfonamide compounds. It is commonly used as a reagent for spectrophotometric determination of trace amounts of fluoride ions. p-nitrophenyl dimethylsulphamate has a nitro group (-NO2) and a dimethylsulphamoyl group (-SO2N(CH3)2) attached to a phenyl ring. It is a yellow crystalline solid with a high melting point and is sparingly soluble in water. p-Nitrophenyl dimethylsulphamate is known for its role in analytical chemistry and biochemistry research, particularly in the study of fluoride ion detection and quantification.

InChI:InChI=1/C8H10N2O5S/c1-9(2)16(13,14)15-8-5-3-7(4-6-8)10(11)12/h3-6H,1-2H3

Upstream product

• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 13360-57-1 dimethylamino sulfonyl chloride 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 94838-58-1 tert-butyl 4-nitrobenzylcarbamate 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 1694-20-8 4-nitrostilbene 
• 131061-15-9 3-(4-nitrophenyl)acrylic acid n-butyl ester 
• 2301-25-9 1-(4-nitrophenyl)-1H-imidazole 

Relevant articles and documents

N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst

An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is

AMINOLYSIS AND HYDROLYSIS OF SULPHAMATE ESTERS: SUBSTANTIAL N=S BONDING IN THE TRANSITION STATE LEADING TO N=SULFONYLAMINES

The aminolysis and hydrolysis of several sulphamate esters, RNHSO2ONp (R = PhCH2, Ph, 4-MeC6H4, 3-MeC6H4, 4-FC6H4, 4-ClC6H4, 3-ClC6H4, H; Np = 4-NO2C6H4) were been studied in 50 percent (v/v) aqueous acetonitrile at various temperatures.Reaction of the esters with an amine (R1NH2) gives -ONp and both sulphamide, (RNHSO2NHR1) and sulphamate (RNHSO2O-R1NH3+) products.First-order rates were determined by the appearance of -ONp and sometimes also by the disappearance of ester.The reaction was found to be independent of amine type and concentration and at the high pHs that obtain the substrate esters are fully ionized.A Hammett ρacyl of -1.8 was obtained for the decomposition of the sulphamate anions and this is consistent with substantial N=S bonding in the transition state leading to N-sulphonylamine, RN=SO2.This intermediate then partitions very rapidly, reacting with R1NH2 and H2O respectively. ΔH*, ΔS* and a deuterium solvent isotope effect were determined and were also interpreted in favour of the proposed mechanism.The dimethyl sulphamate ester (Me2NSO2ONp) does not react under the conditions used.

Betylates. 1. Synthesis and reactions of an isolable betylate, N,N-dimethyl-N-(phenoxysulfonyl)methanaminium fluorosulfate

Phenyl betylate fluorosulfate (2), the first example of a "betylate" (trialkylammoniosulfate ester), has been prepared by methylation of phenyl N,N-dimethylsulfamate with methyl fluorosulfate.Nucleophiles react with 2 either by attack on the sulfur or methyl carbon atoms, but with no sign of any products derived from benzyne or the phenyl cation.A synthesis of enol N,N-dimethylsulfamates has been devised using a reagent, Me2NSO2N(1+)Me3 FSO3(1-), prepared from tetramethylsulfamide and methyl fluorosulfate, but no satisfactory method was found for converting the sulfamic ester to the betylate.Evidence is presented that phenyl chlorosulfate reacts with trimethylamine to give the phenylbetylate which then undergoes further reaction.