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.
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]
Biochemistryedit
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]
Disinfectionedit
OPA is commonly used as a high-leveldisinfectant 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)edit
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]
^ abIUPAC 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. IUPAC–RSC. ISBN978-0-85404-182-4.
^ abBill, J. C.; Tarbell, D. S. (1954). "o-Phthalaldehyde". Organic Syntheses. 34: 82. doi:10.15227/orgsyn.034.0082.
^"Infection Control in the Physician's Office" (PDF). College of Physicians and Surgeons of Ontario. 2004.
^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.
^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) ISBN0834217015
April 04, 2024
phthalaldehyde, sometimes, also, phthalaldehyde, ortho, phthalaldehyde, chemical, compound, with, formula, c6h4, three, isomers, benzene, dicarbaldehyde, related, phthalic, acid, this, pale, yellow, solid, building, block, synthesis, heterocyclic, compounds, r. 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 lt 11 5 Its solutions degrade upon UV illumination and exposure to air Phthalaldehyde NamesIUPAC name Phthalaldehyde 1 Preferred IUPAC name Benzene 1 2 dicarbaldehyde 1 Other names Benzene 1 2 dicarboxaldehydeo Phthalaldehydeo Phthalic dicarboxaldehydePhthaldialdehydeIdentifiersCAS Number 643 79 8 Y3D model JSmol Interactive imageChEBI CHEBI 70851 YChemSpider 4642 YECHA InfoCard 100 010 367EC Number 211 402 2PubChem CID 4807RTECS number TH6950000UNII 4P8QP9768A YUN number 2923CompTox Dashboard EPA DTXSID6032514InChI InChI 1S C8H6O2 c9 5 7 3 1 2 4 8 7 6 10 h1 6HSMILES O Cc1ccccc1C OPropertiesChemical formula C 8H 6O 2Molar mass 134 134 g mol 1Appearance Yellow solidDensity 1 19 g mLMelting 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 Solubility in water LowHazardsOccupational safety and health OHS OSH Main hazards Toxic IrritantGHS labelling PictogramsSignal word DangerHazard statements H228 H301 H314 H315 H317 H335 H373 H410Precautionary statements 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 P501Flash 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 N verify what is Y N Infobox references Contents 1 Synthesis and reactions 2 Biochemistry 3 Disinfection 4 Poly phthalaldehyde 5 In winemaking 6 Isomeric phthalaldehydes 7 ReferencesSynthesis and reactions editThe compound was first described in 1887 when it was prepared from a a a a 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 nbsp Biochemistry editOPA 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 editOPA 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 editOPA 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 editThe 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 editisophthalaldehyde benzene 1 3 dicarbaldehyde terephthalaldehyde benzene 1 4 dicarbaldehyde References edit a b 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 IUPAC RSC ISBN 978 0 85404 182 4 a b Bill J C Tarbell D S 1954 o Phthalaldehyde Organic Syntheses 34 82 doi 10 15227 orgsyn 034 0082 Phthaldialdehyde from Sigma Aldrich Colson A Gautier H 1887 Nouveau Mode de Chloruration des Carbures Annales de Chimie 6 11 28 Zuman Petr 2004 Reactions of Orthophthalaldehyde with Nucleophiles Chemical Reviews 104 7 3217 38 doi 10 1021 cr0304424 PMID 15250740 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 Protocol by Uptima Infection Control in the Physician s Office PDF College of Physicians and Surgeons of Ontario 2004 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 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 Retrieved from https en wikipedia org w index php title Phthalaldehyde amp oldid 1167632278, wikipedia, wiki, book, books, library,
