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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 265834945 | verifiedrevid = 394292963
| ImageFileL1 = Phthalaldehyde-2D-skeletal.svg | ImageFile = Phthalaldehyde Structural Formulae.png
⚫ | ImageName = Skeletal formula of ''o''-phthaldehyde
| ImageSizeL1 = 105px
| PIN = Benzene-1,2-dicarbaldehyde<ref name="iupac">{{BlueBook2013|rec=66.6.1.2.2}}</ref>
⚫ | ImageNameL1 = Skeletal formula of O-phthaldehyde
| ImageFileR1 = Phthalaldehyde-3D-balls.png | IUPACName = Phthalaldehyde<ref name="iupac" />
⚫ | OtherNames = Benzene-1,2-dicarboxaldehyde<br />''o''-Phthalaldehyde<br />''o''-Phthalic dicarboxaldehyde<br />Phthaldialdehyde
| ImageSizeR1 = 125px
⚫ |Section1={{Chembox Identifiers
| ImageNameR1 = Ball-and-stick model
| IUPACName = o-Phthalaldehyde
⚫ | OtherNames = o-Phthalic dicarboxaldehyde<br/>Benzene-1,2-dicarboxaldehyde<br/>Phthaldialdehyde
⚫ | Section1 = {{Chembox Identifiers
| Abbreviations = | Abbreviations =
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 643-79-8 | CASNo = 643-79-8
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS =
| InChI = | ChemSpiderID = 4642
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | RTECS = TH6950000}}
| ChEBI = 70851
⚫ | Section2 = {{Chembox Properties
| EC_number = 211-402-2
| Formula = C<sub>8</sub>H<sub>6</sub>O<sub>2</sub>
| PubChem = 4807
| MolarMass = 134.13 g/mol
⚫ | RTECS = TH6950000
⚫ | Appearance = yellow solid
| Density = | UNNumber = 2923
| UNII_Ref = {{fdacite|correct|FDA}}
| MeltingPt = 114-116 °C
| BoilingPt = | UNII = 4P8QP9768A
| SMILES = O=Cc1ccccc1C=O
⚫ | Solubility in water = low
| InChI = InChI=1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H
⚫ | SolubleOther = organic solvents
}}
⚫ |Section2={{Chembox Properties
| C=8 | H=6 | O=2
⚫ | Appearance = Yellow solid
| Density = 1.19 g/mL
| MeltingPtC = 55.5–56
| MeltingPt_ref = <ref name=OS>{{cite journal |doi=10.15227/orgsyn.034.0082|title=''o''-Phthalaldehyde|journal=Organic Syntheses|year=1954|first1=J. C.|last1=Bill|first2=D. S.|last2=Tarbell |volume=34|page=82}}</ref>
| BoilingPtC = 266.1
⚫ | Solubility = Low
⚫ | SolubleOther =
| Solvent = | Solvent =
| pKa = }} | pKa = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
⚫ | MainHazards = Toxic, Irritant
| EUClass =
| EUIndex =
⚫ | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| RPhrases = 36/37/38
| GHSSignalWord = Danger
| SPhrases = 26-28-36
| HPhrases = {{H-phrases|228|301|314|315|317|335|373|410}}
| RSPhrases =
| PPhrases = {{P-phrases|210|240|241|260|261|264|270|271|272|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|314|321|330|332+313|333+313|362|363|370+378|391|403+233|405|501}}
| FlashPt =
| FlashPtC = 132
| FlashPt_ref = <ref name=Sigma> from ]</ref>
| PEL = }} | PEL = }}
}} }}


'''o-Phthalaldehyde''' or '''''ortho''-phthalaldehyde''' is the ] with the formula C<sub>6</sub>H<sub>4</sub>(CHO)<sub>2</sub>. Often abbreviated OPA, the molecule is a di], consisting of two ] (CHO) groups attached to adjacent carbon centres on a ] ring. This pale yellow solid is a building block in the synthesis of ]s and a ] in the analysis of ]s. '''Phthalaldehyde''' (sometimes also '''''o''-phthalaldehyde''' or '''''ortho''-phthalaldehyde''', '''OPA''') is the ] with the formula C<sub>6</sub>H<sub>4</sub>(CHO)<sub>2</sub>. It is one of three isomers of benzene ], related to ]. This pale yellow solid is a building block in the synthesis of ]s and a ] in the analysis of ]s. OPA dissolves in water solution at pH < 11.5. Its solutions degrade upon UV illumination and exposure to air.


==Synthesis== ==Synthesis and reactions==
The molecule was first described in 1887 when it was prepared from α,α,α',α’-tetrachloro-].<ref>Colson, A.; Gautier, H. "Nouveau Mode de Chloruration des Carbures" '']'' (Paris), 1887, volume 6, number 11, pp. 28.</ref> A more modern synthesis is similar: the hydrolysis of the related tetrabromoxylene using potassium ], followed by purification by ].<ref>Bill J. C.; Tarbell, D. S. “o-Phthalaldehyde” Organic Syntheses, Collected Volume 4, p.807 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0807.pdf</ref> The reactivity of OPA is complicated by the fact that with water it forms both a mono- and dihydrate, C<sub>6</sub>H<sub>4</sub>(CHO)(CH<sub>2</sub>OH) and C<sub>6</sub>H<sub>4</sub>(CH<sub>2</sub>OH)<sub>2</sub>, respectively.<ref>Zuman, H. "Reactions of Orthophthalaldehyde with Nucleophiles" Chemical Reviews 2004; volume 104, pp. 3217-3238. {{DOI|10.1021/cr0304424}}</ref> The compound was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-].<ref>{{Cite journal |author1=Colson, A. |author2=Gautier, H. | title = Nouveau Mode de Chloruration des Carbures | journal = ] | year = 1887 | volume = 6 | issue = 11 | page = 28}}</ref> A more modern synthesis is similar: the hydrolysis of the related ] using potassium ], followed by purification by ].<ref name=OS/>


The reactivity of OPA is complicated by the fact that in water it forms both a mono- and dihydrate, C<sub>6</sub>H<sub>4</sub>(CHO)(CH(OH)<sub>2</sub>) and C<sub>6</sub>H<sub>4</sub>(CH(OH))<sub>2</sub>O, respectively. Its reactions with nucleophiles often involves the reaction of both carbonyl groups.<ref>{{cite journal | doi = 10.1021/cr0304424 | title = Reactions of Orthophthalaldehyde with Nucleophiles | year = 2004 | last1 = Zuman | first1 = Petr | journal = Chemical Reviews | volume = 104 | issue = 7 | pages = 3217–38 | pmid = 15250740}}</ref>
⚫ ==Isomeric phthalaldehydes==

Related to ''o''-phthalaldehyde are the meta and para ]s, which are respectively named ] (m.p. 87-88 °C, CAS# 626-19-7) and ] (m.p. 114-116 °C, CAS# 623-27-8).<!--link when these articles are written-->
]


==Biochemistry== ==Biochemistry==
⚫ OPA is used in a very sensitive ] reagent for assaying ]s or ]s in solution,<ref name="Roth 1971 pp. 880–882">{{cite journal | last=Roth | first=Marc. | title=Fluorescence reaction for amino acids | journal=Analytical Chemistry | publisher=American Chemical Society (ACS) | volume=43 | issue=7 | date=1971-06-01 | issn=0003-2700 | doi=10.1021/ac60302a020 | pages=880–882| pmid=5576608 }}</ref> notably contained in proteins, peptides, and amino acids, by ] and ]. 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 ] (fluorescent ] at 436-475&nbsp;nm (max 455&nbsp;nm) with excitation at 330-390&nbsp;nm (max. 340&nbsp;nm)).<ref></ref>
''Ortho''-phthalaldehyde (OPA) is well soluble, and stable in water solution at pH<11.5. It is however sensitive to UV illumination and air oxidation.

⚫ OPA is used as a very sensitive fluorescent reagent for assaying ]s or ]s in solution, notably contained in proteins, peptides, and aminoacids, by ] and ]. 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 ] (optical ] at 436-475nm (max 455nm) with excitation at 330-390nm (max.340nm))
<ref></ref>.


==Disinfection== ==Disinfection==
''Ortho''-phthalaldehyde is commonly used as a ] ] for medical instruments. 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.<ref>College of Physicians and Surgeons of Ontario. "Infection Control in the Physician's Office". 2004 edition. http://www.cpso.on.ca/Publications/infectioncontrolv2.pdf</ref> OPA is commonly used as a ] ] 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.<ref>{{cite web | publisher = College of Physicians and Surgeons of Ontario | title = Infection Control in the Physician's Office | year = 2004 | url = http://www.cpso.on.ca/uploadedFiles/policies/guidelines/office/Infection_Controlv2.pdf}}</ref>


==Poly(phthalaldehyde)== ==Poly(phthalaldehyde)==
Phthalaldehyde 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 ]. OPA can be polymerized. In the ], 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. ] is used in making a ].<ref>{{Cite journal | last1 = Tsuda | first1 = M. | last2 = Hata | first2 = M. | last3 = Nishida | first3 = R. I. E. | last4 = Oikawa | first4 = S. | title = Chemically amplified resists IV. Proton-catalyzed degradation mechanism of poly(phthalaldehyde) | doi = 10.2494/photopolymer.6.491 | journal = Journal of Photopolymer Science and Technology | volume = 6 | issue = 4 | pages = 491 | year = 1993 | doi-access = free }}</ref>

==In winemaking==
The Nitrogen by ''O''-Phthaldialdehyde Assay (NOPA) is one of the methods used in ] to measure ] (or YAN) needed by ] in order to successfully complete ].<ref name="Zoecklein">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}}</ref>

⚫ ==Isomeric phthalaldehydes==
* ] (benzene-1,3-dicarbaldehyde)
* ] (benzene-1,4-dicarbaldehyde)


==References== ==References==
<references/> <references/>


⚫ ]
==External links==

⚫ ]
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