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 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

<span class="mw-page-title-main">Aromatic compound</span> Compound containing rings with delocalized pi electrons

Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation with their smell.

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

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 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.

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

In chemistry, an ester is a compound 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">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<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. 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. 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, 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">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.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

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

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

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

Maleimide is a chemical compound with the formula H2C2(CO)2NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Maleimides also describes a class of derivatives of the parent maleimide where the NH group is replaced with alkyl or aryl groups such as a methyl or phenyl, respectively. The substituent can also be a small molecule (such as biotin, a fluorescent dye, an oligosaccharide, or a nucleic acid), a reactive group, or a synthetic polymer such as polyethylene glycol. Human hemoglobin chemically modified with maleimide-polyethylene glycol is a blood substitute called MP4.

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

1,1'-Carbonyldiimidazole (CDI) is an organic compound with the molecular formula (C3H3N2)2CO. It is a white crystalline solid. It is often used for the coupling of amino acids for peptide synthesis and as a reagent in organic synthesis.

The nitrosonium ion is NO+, in which the nitrogen atom is bonded to an oxygen atom with a bond order of 3, and the overall diatomic species bears a positive charge. It can be viewed as nitric oxide with one electron removed. This ion is usually obtained as the following salts: NOClO4, NOSO4H (nitrosylsulfuric acid, more descriptively written ONSO3OH) and NOBF4. The ClO−4 and BF−4 salts are slightly soluble in acetonitrile CH3CN. NOBF4 can be purified by sublimation at 200–250 °C and 0.01 mmHg (1.3 Pa).

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

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

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.

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.

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">Sulfenamide</span>

Sulfenamides (also spelled sulphenamides) are a class of organosulfur compounds characterized by the general formula RSNR'2, where R and R' are H, alkyl, or aryl. Sulfenamides have been used extensively in the vulcanization of rubber using sulfur. They are related to the oxidized compounds sulfinamides (RS(O)NR'2) and sulfonamides (RS(O)2NR'2).

<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. American Chemical Society (ACS). 43 (7): 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