Names | |
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Preferred IUPAC name 4-Aminobenzene-1-sulfonic acid [1] | |
Other names | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ECHA InfoCard | 100.004.075 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H7NO3S | |
Molar mass | 173.19 |
Density | 1.485 |
Melting point | 288 °C (550 °F; 561 K) |
12.51 g/L | |
Acidity (pKa) | 3.23 (H2O) [2] |
Related compounds | |
Related sulfonic acids | Benzenesulfonic acid p-Toluenesulfonic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Sulfanilic acid (4-aminobenzenesulfonic acid) is an organic compound with the formula H3NC6H4SO3. It is an off-white solid. It is a zwitterion, which explains its high melting point. It is a common building block in organic chemistry. [3]
Sulfanilic acid can be produced by sulfonation of aniline with concentrated sulfuric acid. [4] This proceeds via phenylsulfamic acid; a zwitterion with a N-S bond. Eugen Bamberger originally proposed a mechanism involving a series of intramolecular rearrangements, with phenylsulfamic acid forming orthanilic acid, which rearranged to sulfanilic acid on heating. [5] [6] Subsequent radiosulphur studies showed that the process is intermolecular, with the phenylsulfamic acid desulfating to generate sulfur trioxide, which then reacts with aniline at the para position in manner similar to a Bamberger rearrangement. [7] [8]
As the compound readily forms diazo compounds, it is used to make dyes and sulfa drugs. [3] This property is also used for the quantitative analysis of nitrate and nitrite ions by diazonium coupling reaction with N-(1-Naphthyl)ethylenediamine, resulting in an azo dye, and the concentration of nitrate or nitrite ions were deduced from the color intensity of the resulting red solution by colorimetry. [9]
It is also used as a standard in combustion analysis and in the Pauly reaction.
Reflecting its wide use, sulfanilic acid is found in the leachates of landfills. [10] It is produced by reduction of some azo dyes. [11]
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.
The Griess test is an analytical chemistry test which detects the presence of nitrite ion in solution. One of its most important uses is the determination of nitrite in drinking water. The Griess diazotization reaction, on which the Griess reagent relies, was first described in 1858 by Peter Griess. The test has also been widely used for the detection of nitrates, which are a common component of explosives, as they can be reduced to nitrites and detected with the Griess test.
Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.
In organic chemistry, an azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated carbon act as a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.
In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. Named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978), the method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids.
The Baker–Venkataraman rearrangement is the chemical reaction of 2-acetoxyacetophenones with base to form 1,3-diketones.
The Bamberger triazine synthesis in organic chemistry is a classic organic synthesis of a triazine first reported by Eugen Bamberger in 1892.
4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.
The Kornblum–DeLaMare rearrangement is a rearrangement reaction in organic chemistry in which a primary or secondary organic peroxide is converted to the corresponding ketone and alcohol under acid or base catalysis. The reaction is relevant as a tool in organic synthesis and is a key step in the biosynthesis of prostaglandins.
3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes.
The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.
The Barton reaction, also known as the Barton nitrite ester reaction, is a photochemical reaction that involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol.
The Achmatowicz reaction, also known as the Achmatowicz rearrangement, is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish Chemist Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.
N-Chlorosuccinimide ("NCS")is the organic compound with the formula C2H4(CO)2NCl. A white solid, it is used for chlorinations. It is also used as a mild oxidant. NCS is related to succinimide, but with N-Cl in place of N-H. The N–Cl bond is highly reactive, and NCS functions as a source of "Cl+".
Electrophilic amination is a chemical process involving the formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen.
Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.
Silver nitrite is an inorganic compound with the formula AgNO2.
Silica sulfuric acid, a solid acid, is prepared by soaking silica gel with sulfuric acid. SSA is used as a catalyst in different organic synthesis process. Silica sulfuric acid is considered as cheap, nonhazardous and easy to handle solid acid catalyst with high acidity.
The name 'sulfanilic acid' is not retained.