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Names | |
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Preferred IUPAC name Sodium 4-{[4-(dimethylamino)phenyl]diazenyl}benzene-1-sulfonate | |
Other names Sodium 4-[(4-dimethylamino)phenylazo]benzenesulfonate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.008.115 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 3143 |
CompTox Dashboard (EPA) | |
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Properties | |
C14H14N3NaO3S | |
Molar mass | 327.33 g·mol−1 |
Appearance | Orange or yellow solid [1] |
Density | 1.28 g/cm3 |
Melting point | >300 °C (572 °F; 573 K) (not precisely defined) |
Boiling point | Decomposes [1] |
5 g/L (20 °C) | |
Solubility in diethyl ether | Insoluble [2] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Toxic (T) |
GHS labelling: | |
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Danger | |
H301 | |
P308, P310 | |
NFPA 704 (fire diamond) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 60 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Methyl orange is a pH indicator frequently used in titration because of its clear and distinct color variance at different pH values. Methyl orange shows red color in acidic medium and yellow color in basic medium. Because it changes color at the pKa of a mid strength acid, it is usually used in titration of strong acids in weak bases that reach the equivalence point at a pH of 3.1-4.4. [3] Unlike a universal indicator, methyl orange does not have a full spectrum of color change, but it has a sharp end point. In a solution becoming less acidic, methyl orange changes from red to orange and, finally, to yellow—with the reverse process occurring in a solution of increasing acidity.
In a solution that decreases in acidity, methyl orange moves from the color red to orange and finally to yellow with the opposite occurring for a solution increasing in acidity. This color change from yellow to red occurs because the protons in the acidic solution react with the N=N bond of the molecule, protonating one of them and changing the visible light absorption of the molecule to reflect more red light than orange/yellow.
Methyl orange(pH indicator) | ||
below pH 3.1 | above pH 4.4 | |
3.1 | ⇌ | 4.4 |
In an acid, it is reddish and in alkali, it is yellow. Methyl orange has a pKa of 3.47 in water at 25 °C (77 °F). [4]
Methyl orange in xylene cyanol solution(pH indicator) | ||
below pH 3.2 | above pH 4.2 | |
3.2 | ⇌ | 4.2 |
Modified (or screened) methyl orange, an indicator consisting of a solution of methyl orange and xylene cyanol, changes from grey-violet to green as the solution becomes more basic.
Methyl orange has mutagenic properties. [2] When methyl orange is put under oxidative stress, one of the double-bonded nitrogen atoms that connects the aromatic rings gets radicalized and can further break down into reactive oxygen species or anilines, which are carcinogenic and can mutate DNA. [5] Various bacteria and enzymes can also cause this breakdown to occur.
Methyl orange is an azobenzene derivative that can be formed from dimethylaniline and sulfanilic acid, first through a diazonium salt formation with the sulfanilic acid, followed by a nucleophilic attack from the dimethylaniline and rearomatization. [6]
The absorption of methyl orange on the UV-vis spectrum is between 350-550 nm, with its peak at 464 nm. This is in the green-purple visible light range and explains why methyl orange is, in fact, orange. [7]
Titration is a common laboratory method of quantitative chemical analysis to determine the concentration of an identified analyte. A reagent, termed the titrant or titrator, is prepared as a standard solution of known concentration and volume. The titrant reacts with a solution of analyte to determine the analyte's concentration. The volume of titrant that reacted with the analyte is termed the titration volume.
A pH indicator is a halochromic chemical compound added in small amounts to a solution so the pH (acidity or basicity) of the solution can be determined visually or spectroscopically by changes in absorption and/or emission properties. Hence, a pH indicator is a chemical detector for hydronium ions (H3O+) or hydrogen ions (H+) in the Arrhenius model.
Phenolphthalein ( feh-NOL(F)-thə-leen) is a chemical compound with the formula C20H14O4 and is often written as "HIn", "HPh", "phph" or simply "Ph" in shorthand notation. Phenolphthalein is often used as an indicator in acid–base titrations. For this application, it turns colorless in acidic solutions and pink in basic solutions. It belongs to the class of dyes known as phthalein dyes.
Bromothymol blue is a pH indicator. It is mostly used in applications that require measuring substances that would have a relatively neutral pH. A common use is for measuring the presence of carbonic acid in a liquid. It is typically sold in solid form as the sodium salt of the acid indicator.
Chrysoine resorcinol is a synthetic azo dye which was formerly used as a food additive. In Europe, it was banned as a food additive in 1977. In the US, it was banned in 1988.
Congo red is an organic compound, the sodium salt of 3,3′-([1,1′-biphenyl]-4,4′-diyl)bis(4-aminonaphthalene-1-sulfonic acid). It is an azo dye. Congo red is water-soluble, yielding a red colloidal solution; its solubility is greater in organic solvents. The use of Congo red in the textile industry has long been abandoned, primarily because of its carcinogenic properties, but it is still used for histological staining.
Methyl yellow, or C.I. 11020, is an organic compound with the formula C6H5N2C6H4N(CH3)2. It is an azo dye derived from dimethylaniline. It is a yellow solid. According to X-ray crystallography, the C14N3 core of the molecule is planar.
Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antifungal, and anthelmintic (vermicide) properties and was formerly important as a topical antiseptic. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.
The equivalence point, or stoichiometric point, of a chemical reaction is the point at which chemically equivalent quantities of reactants have been mixed. For an acid-base reaction the equivalence point is where the moles of acid and the moles of base would neutralize each other according to the chemical reaction. This does not necessarily imply a 1:1 molar ratio of acid:base, merely that the ratio is the same as in the chemical reaction. It can be found by means of an indicator, for example phenolphthalein or methyl orange.
A chromophore is a molecule which absorbs light at a particular wavelength and emits color as a result. Chromophores are commonly referred to as colored molecules for this reason. The word is derived from Ancient Greek χρῶμᾰ (chroma) 'color', and -φόρος (phoros) 'carrier of'. Many molecules in nature are chromophores, including chlorophyll, the molecule responsible for the green colors of leaves. The color that is seen by our eyes is that of the light not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore indicates a region in the molecule where the energy difference between two separate molecular orbitals falls within the range of the visible spectrum. Visible light that hits the chromophore can thus be absorbed by exciting an electron from its ground state into an excited state. In biological molecules that serve to capture or detect light energy, the chromophore is the moiety that causes a conformational change in the molecule when hit by light.
Methyl red (2-(N,N-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also called C.I. Acid Red 2, is an indicator dye that turns red in acidic solutions. It is an azo dye, and is a dark red crystalline powder. Methyl red is a pH indicator; it is red in pH under 4.4, yellow in pH over 6.2, and orange in between, with a pKa of 5.1. Murexide and methyl red are investigated as promising enhancers of sonochemical destruction of chlorinated hydrocarbon pollutants. Methyl red is classed by the IARC in group 3 - unclassified as to carcinogenic potential in humans.
Patent Blue V, also called Food Blue 5, Sulphan Blue, Acid Blue 3, L-Blau 3, C-Blau 20, Patentblau V, Sky Blue, or C.I. 42051, is a sky blue synthetic triphenylmethane dye used as a food coloring. As a food additive, it has E number E131. It is a sodium or calcium salt of [4-(α- -5-hydroxy- 2,4-disulfophenylmethylidene)-2,5-cyclohexadien-1-ylidene] diethylammonium hydroxide inner salt.
Litmus is a water-soluble mixture of different dyes extracted from lichens. It is often absorbed onto filter paper to produce one of the oldest forms of pH indicator, used to test materials for acidity. In an acidic medium, blue litmus paper turns red, while in a basic or alkaline medium, red litmus paper turns blue. In short, it is a dye and indicator which is used to place substances on a pH scale.
Biebrich scarlet is a molecule used in Lillie's trichrome.
Azobenzene reductase also known as azoreductase (EC 1.7.1.6) is an enzyme that catalyzes the chemical reaction:
Brooker's merocyanine is an organic dye belonging to the class of merocyanines.
Azo violet (Magneson I; p-nitrobenzeneazoresorcinol) is an azo compound with the chemical formula C12H9N3O4. It is used commercially as a violet dye and experimentally as a pH indicator, appearing yellow below pH 11, and violet above pH 13. It also turns deep blue in the presence of magnesium salt in a slightly alkaline, or basic, environment. Azo violet may also be used to test for the presence of ammonium ions. The color of ammonium chloride or ammonium hydroxide solution will vary depending upon the concentration of azo violet used. Magneson I is used to test Be also; it produces an orange-red lake with Be(II) in alkaline medium.
Quinaldine red is a dark green–red or black solid that does not dissolve easily in water. In addition to being used as colored indicator, quinaldine red is also used as a fluorescence probe and an agent in bleaching.
Bromopyrogallol red is frequently used in analytical chemistry as a reagent for spectrophometric analysis and as an complexometric indicator.
Optical air sensors center around the detection of some form of light created by a chemical process, in order to identify or measure amounts of individual molecules. Portable sensors are specifically sensors that are easy to transport and use in the field.