3,5-Dinitrobenzoic acid

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3,5-Dinitrobenzoic acid
Skeletal formula 3,5-dinitrobenzoic acid structure.svg
Skeletal formula
Ball-and-stick model 3,5-dinitrobenzoic-acid-3D-balls.png
Ball-and-stick model
3,5-dinitrobenzoic acid sample.jpg
Names
Preferred IUPAC name
3,5-Dinitrobenzoic acid
Identifiers
3D model (JSmol)
1914286
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.501 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-751-1
PubChem CID
UNII
  • InChI=1S/C7H4N2O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11) Yes check.svgY
    Key: VYWYYJYRVSBHJQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H4N2O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)
    Key: VYWYYJYRVSBHJQ-UHFFFAOYAQ
  • O=[N+]([O-])c1cc(cc([N+]([O-])=O)c1)C(=O)O
Properties
C7H4O6N2
Molar mass 212.118 g/mol
AppearanceYellow or colourless crystals
Melting point 205 to 207 °C (401 to 405 °F; 478 to 480 K)
Acidity (pKa)2.82
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335, H413
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

3,5-Dinitrobenzoic acid is an organic chemical that is an important corrosion inhibitor and is also used in photography. This aromatic compound is used by chemists to identify alcohol components in esters and in the fluorometric analysis of creatinine.

Contents

Synthesis

3,5-dinitrobenzoic acid is obtained from benzoic acid by the nitration reaction with nitric acid in the presence of concentrated sulfuric acid. [1] [2]

3 5 Dinitrobenzoesaure.svg

The nitration can also be started with 3-nitrobenzoic acid, which leads to yields of approximately 98 %. [3]

Properties

3,5-Dinitrobenzoic acid is an odorless, yellowish solid. Due to the mesomeric effect of the two nitro groups, it is more acidic (pKa = 2.82) than benzoic acid (pKa = 4.20) and 3-nitrobenzoic acid (pKa = 3.47).

Uses

3,5-Dinitrobenzoic acid finds use in the identification of various organic substances, especially alcohols, by derivatization. For such an analysis, the substance to be analyzed is reacted with 3,5-dinitrobenzoic acid in the presence of sulfuric acid in order to form a derivate. By doing so, many substances that are liquid or have a low melting point are converted to easily crystallized derivates with sharp melting points. For instance, alcohols can be identified by the melting point of their esters with 3,5-dinitrobenzoic acid. This method is also applicable to a large number of amines.

Identification of isopropanol as a derivate of 3,5-dinitrobenzoic acid:
3,5-dinitrobenzoic acid-2-propylester (mp.: 123 degC ). 3-5-Dinitrobenzoesaure-2-propylester.svg
Identification of isopropanol as a derivate of 3,5-dinitrobenzoic acid:
3,5-dinitrobenzoic acid-2-propylester (mp.: 123 °C ).

Compared to 4-nitrobenzoic acid, another acid that is used similarly, derivates of 3,5-dinitrobenzoic acid have higher melting points, so that it is preferred when the 4-nitrobenzoic acid derivate has a melting point too low to be accurately identified. [4]

For more sensitive compounds, the reaction is carried out using the acid chloride, 3,5-dinitrobenzoyl chloride. This allows for example the identification of amino acids. [1]

Related Research Articles

Acid Chemical compound giving a proton or accepting an electron pair

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

Benzoic acid Chemical compound

Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Carboxylic acid Organic compound

A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixture for glass. Chromic acid may also refer to the molecular species, H2CrO4 of which the trioxide is the anhydride. Chromic acid features chromium in an oxidation state of +6 (or VI). It is a strong and corrosive oxidising agent.

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Acyl halide Chemical compound

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

In chemistry, a chemical test is a qualitative or quantitative procedure designed to identify, quantify, or characterise a chemical compound or chemical group.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

Benzoyl chloride Chemical compound

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<i>p</i>-Toluenesulfonic acid Chemical compound

p-Toluenesulfonic acid (PTSA or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C6H4SO2 group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH.H2O.

Boronic acid

A boronic acid is a compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes. Boronic acids act as Lewis acids. Their unique feature is that they are capable of forming reversible covalent complexes with sugars, amino acids, hydroxamic acids, etc.. The pKa of a boronic acid is ~9, but they can form tetrahedral boronate complexes with pKa ~7. They are occasionally used in the area of molecular recognition to bind to saccharides for fluorescent detection or selective transport of saccharides across membranes.

3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.

Nitrobenzoic acid Index of chemical compounds with the same name

Nitrobenzoic acids are derivatives of benzoic acid. Two are commercially important. They are about ten times more acidic than the parent benzoic acid.

4-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is a pale yellow solid. It is a precursor to 4-nitrobenzoyl chloride, the precursor to the anesthetic procaine and folic acid. It is also a precursor to 4-aminobenzoic acid.

Trichloroacetonitrile Chemical compound

Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of trichloroacetamide. As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility towards hydrolysis.

<i>N</i>-Hydroxyphthalimide Chemical compound

N-Hydroxyphthalimide is the N-hydroxy derivative of phthalimide. The compound can be utilized as a catalyst for oxidation reactions, in particular for the selective oxidation with molecular oxygen under mild conditions.

3,5-Dinitrobenzoyl chloride Chemical compound

3,5-Dinitrobenzoyl chloride (C7H3ClN2O5) is an organic compound with a melting point of 68–69 °C. It is the acyl chloride of 3,5-dinitrobenzoic acid and like it is mainly used in the analysis of organic substances by derivatization.

Ortho effect refers mainly to the set of steric effects and some bonding interactions along with polar effects caused by the various substituents which are in a given molecule altering its chemical properties and physical properties. In a general sense the ortho effect is associated with substituted benzene compounds.

References

  1. 1 2 Saunders, B. C.; Stacey, G. J.; Wilding, I. G. E. (1942). "The Preparation of 3:5-Dinitrobenzoic Acid and 3:5-Dinitrobenzoyl Chloride – Observations on the Acylation of Amino-acids by means of 3:5-Dinitrobenzoyl Chloride and certain other Acid Chlorides". Biochem. J. 36 (3–4): 368–375. doi:10.1042/bj0360368. PMC   1265703 . PMID   16747534.
  2. R. Q. Brewster; Bill Williams; Ross Phillips (1942). "3,5-Dinitrobenzoic Acid". Organic Syntheses . 22: 48. doi:10.15227/orgsyn.022.0048.
  3. Lebedev, B. A.; Dolmatov, V. Yu.; Zubarev, P. S.; Latynov, N. V.; Aleksandrov, M. M.; Ponamareva, R. I (1988). "Preparation of 3,5-dinitrobenzoic acid from meta-nitrobenzoic acid". Pharmaceutical Chemistry Journal . 22 (5): 399–401. doi:10.1007/BF00769656. S2CID   34335456..
  4. 1 2 CRC Handbook of Tables for Organic Compound Identification, Third Edition, 1984, ISBN   0-8493-0303-6.

Literature