Phthalaldehyde

Last updated
Phthalaldehyde
Phthalaldehyde Structural Formulae.png
Names
IUPAC name
Phthalaldehyde [1]
Preferred IUPAC name
Benzene-1,2-dicarbaldehyde [1]
Other names
Benzene-1,2-dicarboxaldehyde
o-Phthalaldehyde
o-Phthalic dicarboxaldehyde
Phthaldialdehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.367 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-402-2
PubChem CID
RTECS number
  • TH6950000
UNII
UN number 2923
  • InChI=1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H
  • O=Cc1ccccc1C=O
Properties
C8H6O2
Molar mass 134.134 g·mol−1
AppearanceYellow solid
Density 1.19 g/mL
Melting point 55.5–56 °C (131.9–132.8 °F; 328.6–329.1 K) [2]
Boiling point 266.1 °C (511.0 °F; 539.2 K)
Low
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, Irritant
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H228, H301, H314, H315, H317, H335, H373, H410
P210, P240, P241, P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P233, P405, P501
Flash point 132 °C (270 °F; 405 K) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phthalaldehyde (sometimes also o-phthalaldehyde or ortho-phthalaldehyde, OPA) is the chemical compound with the formula C6H4(CHO)2. It is one of three isomers of benzene dicarbaldehyde, related to phthalic acid. This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.

Contents

Synthesis and reactions

The compound was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-o-xylene. [4] A more modern synthesis is similar: the hydrolysis of the related tetrabromo-o-xylene using potassium oxalate, followed by purification by steam distillation. [2]

The reactivity of OPA is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively. Its reactions with nucleophiles often involves the reaction of both carbonyl groups. [5]

Orthophthalaldehyde and hydrated forms 001.png

Biochemistry

OPA is used in a very sensitive fluorogenic reagent for assaying amines or sulfhydryls in solution, [6] notably contained in proteins, peptides, and amino acids, by capillary electrophoresis and chromatography. OPA reacts specifically with primary amines above their isoelectric point Pi in presence of thiols. OPA reacts also with thiols in presence of an amine such as n-propylamine or 2-aminoethanol. The method is spectrometric (fluorescent emission at 436-475 nm (max 455 nm) with excitation at 330-390 nm (max. 340 nm)). [7]

Disinfection

OPA is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex OPA or TD-8. Disinfection with a High-level disinfectant such as OPA is indicated for semi-critical instruments that come into contact with mucous membranes or broken skin, such as specula, laryngeal mirrors, and internal ultrasound probes. [8]

Poly(phthalaldehyde)

OPA can be polymerized. In the polymer, one of the oxygen atoms forms a bridge to the other non-ring carbon of the same phthalaldehyde unit, while the other bridges to a non-ring carbon of another phthalaldehyde unit. Poly(phthalaldehyde) is used in making a photoresist. [9]

In winemaking

The Nitrogen by O-Phthaldialdehyde Assay (NOPA) is one of the methods used in winemaking to measure yeast assimilable nitrogen (or YAN) needed by wine yeast in order to successfully complete fermentation. [10]

Isomeric phthalaldehydes

Related Research Articles

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In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Pyridine</span> Heterocyclic aromatic organic compound

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Phenyl group</span> Cyclic chemical group (–C₆H₅)

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

The following outline is provided as an overview of and topical guide to organic chemistry:

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

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<span class="mw-page-title-main">Ninhydrin</span> Chemical compound

Ninhydrin (2,2-dihydroxyindane-1,3-dione) is an organic compound with the formula C6H4(CO)2C(OH)2. It is used to detect ammonia and amines. Upon reaction with these amines, ninhydrin gets converted into deep blue or purple derivatives, which are called Ruhemann's purple. Ninhydrin is most commonly used to detect fingerprints in forensic cases, as the terminal amines of lysine residues in peptides and proteins sloughed off in fingerprints react with ninhydrin.

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<span class="mw-page-title-main">Michael addition reaction</span> Reaction in organic chemistry

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<span class="mw-page-title-main">Maleimide</span> Chemical compound

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<span class="mw-page-title-main">Carbonyldiimidazole</span> Chemical compound

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In organic chemistry, umpolung or polarity inversion is the chemical modification of a functional group with the aim of the reversal of polarity of that group. This modification allows secondary reactions of this functional group that would otherwise not be possible. The concept was introduced by D. Seebach and E.J. Corey. Polarity analysis during retrosynthetic analysis tells a chemist when umpolung tactics are required to synthesize a target molecule.

<span class="mw-page-title-main">Biuret test</span> Chemical test for detecting peptide bonds

In chemistry, the biuret test, also known as Piotrowski's test, is a chemical test used for detecting the presence of at least two peptide bonds in a molecule. In the presence of peptides, a copper(II) ion forms mauve-colored coordination complexes in an alkaline solution. The reaction was first observed in 1833; In Poland, the biuret test is also known as Piotrowski's test in honor of the Polish physiologist Gustaw Piotrowski who independently rediscovered it in 1857. Several variants on the test have been developed, such as the BCA test and the Modified Lowry test.

<span class="mw-page-title-main">Cyclohexenone</span> Chemical compound

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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.

<span class="mw-page-title-main">Xylylene</span>

In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides.

Tetrabromo-<i>o</i>-xylene Chemical compound

α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:

<span class="mw-page-title-main">Terephthalaldehyde</span> Chemical compound

Terephthalaldehyde (TA) is an organic compound with the formula C6H4(CHO)2. It is one of three isomers of benzene dicarboxaldehyde, in which the aldehyde moieties are positioned in the para conformation on the benzene ring. Terephthalaldehyde appears as a white to beige solid, typically in the form of a powder. It is soluble in many organic solvents, such as alcohols (e.g., methanol or ethanol) and ethers (e.g., tetrahydrofuran or diethylether).

References

  1. 1 2 IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-66.6.1.2.2". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN   978-0-85404-182-4.
  2. 1 2 Bill, J. C.; Tarbell, D. S. (1954). "o-Phthalaldehyde". Organic Syntheses. 34: 82. doi:10.15227/orgsyn.034.0082.
  3. Phthaldialdehyde from Sigma-Aldrich
  4. Colson, A.; Gautier, H. (1887). "Nouveau Mode de Chloruration des Carbures". Annales de Chimie . 6 (11): 28.
  5. Zuman, Petr (2004). "Reactions of Orthophthalaldehyde with Nucleophiles". Chemical Reviews. 104 (7): 3217–38. doi:10.1021/cr0304424. PMID   15250740.
  6. Roth, Marc. (1971-06-01). "Fluorescence reaction for amino acids". Analytical Chemistry. 43 (7). American Chemical Society (ACS): 880–882. doi:10.1021/ac60302a020. ISSN   0003-2700. PMID   5576608.
  7. Protocol by Uptima
  8. "Infection Control in the Physician's Office" (PDF). College of Physicians and Surgeons of Ontario. 2004.
  9. Tsuda, M.; Hata, M.; Nishida, R. I. E.; Oikawa, S. (1993). "Chemically amplified resists IV. Proton-catalyzed degradation mechanism of poly(phthalaldehyde)". Journal of Photopolymer Science and Technology. 6 (4): 491. doi: 10.2494/photopolymer.6.491 .
  10. B. Zoecklein, K. Fugelsang, B. Gump, F. Nury Wine Analysis and Production pgs 152-163, 340-343, 444-445, 467 Kluwer Academic Publishers, New York (1999) ISBN   0834217015